Ultimate Road Trip: Route 66
- shannastewart4443
- Apr 29
- 33 min read
"Adventure is worthwhile in itself." —Amelia Earhart
The open road is calling, and there’s no better place to answer than the legendary Route 66—the highway that fueled the dreams of countless travelers and adventurers. A journey down this historic route isn’t just a road trip; it’s a time capsule of neon-lit diners, quirky roadside attractions, and landscapes that stretch beyond the horizon. Whether you're chasing nostalgia, uncovering hidden gems, or simply craving the freedom of the road, Route 66 delivers an adventure unlike any other. So, buckle up, roll down the windows, and let the rhythmic hum of the asphalt guide you through America’s most iconic highway—because every mile tells a story, and it’s yours to write.
Tips for an excellent adventure:
🚗 Embrace the detours – Some of the best moments happen when you take an unexpected turn. Route 66 is full of hidden gems!
📸 Capture the quirky roadside attractions – From giant muffler men to Cadillac Ranch, keep your camera ready for one-of-a-kind photo ops.
🍔 Eat at vintage diners – Skip the fast food and enjoy classic roadside meals at historic diners like Lou Mitchell’s in Chicago or The Big Texan in Amarillo.
🛣 Visit the ghost towns – Route 66 has a few abandoned towns that feel frozen in time—perfect for a little eerie exploration.
🎶 Make a road trip playlist – Fill it with classic tunes like “Route 66” by Bobby Troup, old-school rock, or whatever fuels your adventure.
🏁 Talk to the locals – They have the best stories and insider tips for Route 66 treasures that aren’t in guidebooks.
🌅 Time your stops for golden hour – Sunrises and sunsets along Route 66 make for jaw-dropping views.
🛍 Pick up souvenirs from quirky shops – Route 66 is packed with retro gas stations, neon-lit motels, and funky roadside gift shops.
✨ Leave room for spontaneity – The beauty of this trip is going with the flow and soaking in the sights, sounds, and surprises of the open road.
This road trip will take us from Chicago, then stops through 11 different towns across the U.S. and ends in Santa Monica, California. We will traverse over 2,200 miles, visit 7 states, and make 11 overnight stops along the way. I have allotted 3 weeks for this trip, but you could stay shorter/longer in each town.
Here is a link to the map: Santa Monica Trip Roadtrip - Roadtrippers
The stops include:
Best time to drive Route 66:
Spring (April–June) – Mild weather and blooming parks.
Summer (July–September) – Festivals, outdoor concerts, and lakefront activities.
Fall (October–November) – Crisp air and beautiful autumn colors.
Winter (December–March) – Holiday lights, ice skating, and cozy indoor attractions.
Days 1 - 3: Chicago, Illinois (Chi-Town)
Chicago is a fantastic city known for its iconic architecture, deep-dish pizza, world-class museums, and lively neighborhoods. Whether you're exploring the Magnificent Mile, catching a show at The Chicago Theatre, or taking in the skyline from Willis Tower, Chicago has plenty to offer.
Where to stay in Chicago:
Royal Sonesta Chicago River North
4-Star Hotel
In a city as colossal as Chicago — wide boulevards, soaring architecture — it’s only natural that a boutique hotel should want to scale up. Fortunately, this is something Sonesta does especially well, building towering, all-the-amenities hotels that retain the character and warmth of a boutique, and the Royal Sonesta Chicago River North is a textbook example. It’s got the beautiful sky-scraping pool, the spacious 24-hour fitness center and all the full-on business facilities expected of a modern high-rise hotel. But it’s also a friendly enough place that kids get special attention, pets are encouraged and Midwestern generosity abounds — it’s all proof that going big doesn’t have to mean growing cold.
261 rooms and suites, all comfortably stylish without being ostentatious, offer lots of layouts to choose from. Even the most basic have beds with triple Frette sheeting and down comforters, a large business-friendly desk and a 37” HDTV. The City View rooms add floor-to-ceiling windows at an altitude where they count, and the various suites, though spacious and generously appointed throughout, shine brightest in the bathrooms: they’re big, with granite-topped vanities, Fuji soaking tubs and separate marble showers.
The hotel’s location in the River North neighborhood fits its grown-up boutique sensibilities perfectly. Outside Manhattan, nowhere else in the U.S. has a greater concentration of art galleries (there are over 100 here), and the food scene, with more options than anywhere else in the city, is likewise a draw to Chicagoans and visitors alike. No doubt you can have your gigantic steak here, but with all the other options, you can easily beat it, too. Like the hotel, River North presents a more modern image of Chicago — confidently cosmopolitan, without a hint of “second-city” insecurity.
Eurostars Magnificent Mile
4-Star Hotel
Eurostars Magnificent Mile is a boutique hotel that believes in life’s small pleasures. This hedonistic commitment can be seen in the numerous details that accompany your stay. From its sleek contemporary design to an award-winning spa, this hotel has been designed to create the perfect environment for enjoying a unique experience, where avant-garde art, designer furniture and a classical feel come together with the beauty of the natural elements and cutting-edge technology.
Decidedly personal and daringly original, Eurostars Magnificent Mile offers all the luxury of a high-end hotel experience, with a more relaxed and approachable philosophy. Each room has been painstakingly designed down to the finest detail to keep the hotel’s character imaginative, all while meeting the needs of each guest.
Culture-loving travelers will find the perfect getaway right in the heart of bustling Chicago. Located in River North, a stone’s throw from the world-famous Michigan Avenue, Eurostars Magnificent Mile is within walking distance of the city’s vibrant cultural scene.
The St. Regis Chicago
5-Star Hotel
The St. Regis has all of the niceties you’d expect of a hotel of this caliber. It has a great location where the river meets Lake Michigan and the views—well, they’re classic Chicago skyline. The rooms and suites are comfortably luxurious with a smart style and plenty of space to stretch out, and the amenities are top notch (think two restaurants and a bar, plus a 12,000-square-foot wellness center that puts most hotel spas to shame) but the real reason most stay here is the service.
Things to do in Chicago:
Millennium Park & Cloud Gate ("The Bean") – A must-see sculpture reflecting the city’s skyline.
Art Institute of Chicago – One of the best art museums in the world, featuring works by Van Gogh, Monet, and Picasso.
Willis Tower Skydeck – Step onto the glass-floored Ledge for breathtaking views of the city.
Museum of Science and Industry – A fascinating museum with interactive exhibits.
Chicago Cultural Center – A stunning architectural gem with free exhibits and performances.
Buckingham Fountain – One of the largest fountains in the world, located in Grant Park.
Chicago Riverwalk – A scenic walkway with restaurants, bars, and boat tours.
Navy Pier – Home to the Centennial Wheel, shops, and waterfront dining.
Chicago Waterworks Visitors Center – A great resource for planning your trip.
Food & Dining
Chicago is famous for its deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. Be sure to try:
Lou Malnati’s or Giordano’s for deep-dish pizza.
Portillo’s for a classic Chicago-style hot dog.
Al’s Beef for an authentic Italian beef sandwich.
Days 3 - 5: Springfield, Illinois "Birthplace of Route 66"
(about 3.5-hour drive)
Springfield, Illinois, is a historic city known for its deep connections to Abraham Lincoln, charming Route 66 attractions, and lively cultural scene.
Things to see on route to Springfield:
Historic Route 66 Begin Sign – Start your journey at the official Route 66 starting point in downtown Chicago.
Dell Rhea’s Chicken Basket (Willowbrook, IL) – A Route 66 classic serving crispy fried chicken since 1946.
Gemini Giant (Wilmington, IL) – A 30-foot-tall Muffler Man statue wearing a space helmet, perfect for a photo op.
Odell Standard Oil Gas Station (Odell, IL) – A restored 1932 gas station, offering a glimpse into Route 66’s past.
Route 66 Hall of Fame & Museum (Pontiac, IL) – A free museum packed with Route 66 memorabilia and vintage cars.
Paul Bunyon Hot Dog Statue (Atlanta, IL) – A giant statue of Paul Bunyon holding a hot dog, one of four roadside giants in Illinois.
Lincoln’s Tomb (Springfield, IL) – Pay tribute to Abraham Lincoln at his final resting place in Oak Ridge Cemetery.
Meramac Caves (Sullivan, IL) - a system of caves that stretches over 4 miles long. These caverns are the largest commercial caves in the state and are home to the rare Ozark cavefish, a species that can only be found in a few locations in the world.
Where to stay in/near Springfield:
Crowne Plaza Springfield by IHG
3-Star Hotel
Great Hotel & Convention Center on Famous Route 66! The Crowne Plaza Springfield – Convention Center is conveniently located on I-55 & I-72, better known as Historic Route 66. Near the University of Illinois Springfield, the hotel is perfect for those coming in to visit the school or catch a game at one of the nearby sports complexes. With a short drive to Downtown Springfield, history buffs will enjoy a visit to the Lincoln Home National Historic Site and the Abraham Lincoln Presidential Library and Museum. Other nearby attractions include Knight’s Action Park and the Illinois State Fairgrounds. The complimentary shuttle operates a generous 3-mile radius and takes you to UIS, the Amtrak train station, and Abraham Lincoln Capital Airport. The accommodations also offer Free Wi-Fi, parking, and always open business center. Maintain your workout routine at our 24-hour fitness center, go for a swim in the 14th floor indoor pool, or relax in the hot tub and dry sauna. Each room is equipped with a mini-refrigerator, Keurig, and 43” TV.
Inn at 835 Boutique Hotel
3-Star Hotel
Historic architecture meets modern convenience at the beautiful Inn at 835. Located centrally near downtown Springfield, IL, just two blocks from the Illinois State Capitol Building in the Aristocracy Hill Neighborhood. Our peaceful surroundings provide a quiet setting to leisurely read the morning newspaper or enjoy a few moments of calm before a busy day.
Each evening, relax and unwind in our guest sitting room and savor a glass of wine or retire to your room with freshly baked warm cookies each night of your stay.
Villa DeWolf (42 minutes' drive from Springfield)
4-Star Hotel
Villa DeWolf is an elegant Boutique Hotel/B&B located in the historic, 1857 Ayers Mansion in Jacksonville, IL. Enjoy all of Villa Dewolf, including luxurious suites, dining room, parlor, grand ballroom, library, game room, gourmet breakfast and a personal tour provided by the owner. Villa DeWolf is a beautiful place to book your next stay or host your special event or wedding.
Things to do in Springfield and Jacksonville:
Springfield, IL
Abraham Lincoln Presidential Library and Museum – A must-visit for Lincoln enthusiasts, featuring interactive exhibits and historical artifacts.
Lincoln Home National Historic Site – Step inside Lincoln’s only home, beautifully preserved with guided tours.
Old State Capitol – A stunning historic building where Lincoln delivered speeches and debated politics.
Lincoln Tomb & War Memorials – Pay tribute to Lincoln at his final resting place in Oak Ridge Cemetery.
Route 66 Attractions – Springfield is packed with quirky Route 66 stops, including the Cozy Dog Drive-In and Route 66 Motorheads Museum.
Springfield City Scavenger Hunt – A fun way to explore the city while solving clues.
Live Music at Route 66 Motorheads Bar & Grill – Enjoy classic rock and themed events.
Jacksonville, IL
Prairieland Heritage Museum – A non-profit museum showcasing agriculture and pioneer history.
Big Eli Ferris Wheel – A historic Ferris wheel operated by the Jacksonville Rotary Club. Jacksonville Symphony Orchestra – Enjoy live classical performances at Rammelkamp Chapel. Lake Jacksonville – A top bass fishing lake with scenic trails and picnic spots.
David Strawn Art Gallery – A local art gallery featuring rotating exhibits.
Jacksonville Raceway – Catch high-speed stock car races at the Morgan County Fairgrounds. Market House Antiques – A treasure trove of vintage finds.
Days 5 -7: Drive to St. Louis, Missouri "The Lou"
(about 1.5 hours' drive)
Traveling to St. Louis via Route 66 is a journey through history, Americana, and scenic landscapes. As one of the largest cities along the Mother Road, St. Louis offers a mix of iconic landmarks, cultural attractions, and nostalgic Route 66 stops.
Things to see on route to St. Louis:
Litchfield Museum & Route 66 Welcome Center – A great place to learn about the history of Route 66 and see vintage memorabilia.
Cozy Dog Drive-In – Famous for inventing the corn dog on a stick, this Springfield staple is a must-visit.
Motorheads Bar & Grill – A Route 66-themed restaurant and museum featuring classic cars and neon signs.
Chain of Rocks Bridge – A historic bridge that once carried Route 66 traffic over the Mississippi River.
Manners Park – A scenic park in Taylorville, IL, perfect for a quick stop to stretch your legs.
Where to stay in St. Louis:
Seven Gables Inn
3-Star Hotel
The Seven Gables Inn is a charming boutique hotel in Saint Louis that provides delightful accommodations with the intimacy of a bed and breakfast. Located just fifteen minutes from Lambert Airport and ten minutes from downtown St. Louis, you can find the Inn nestled amid specialty shops, art galleries and the area's finest eateries. This bustling Clayton business district is also home to more than 80 Forbes and Fortune 500 offices. Built in 1926 as part of the Tudor Revival, the inn was remarkably sophisticated for its time and place in Clayton. Begin your day at our intimate boutique hotel. The Inn also features complimentary wireless Internet access and delicious authentic dining at Seven Restaurant. Experience a bit of ambiance on the back patio or choose the expansive front terrace. Whether traveling for business or pleasure, our St. Louis luxury hotel exceeds all expectations.
21c Museum Hotel
4-Star Hotel
The 21c Museum Hotels, true to their name, are known for bringing museum-quality contemporary art collections and world-class luxury boutique hospitality to cities where neither one can be taken for granted — not places like New York or Los Angeles but Louisville, Kentucky or Bentonville, Arkansas. For their tenth installment they’ve chosen St. Louis, Missouri, and turned a century-old Renaissance Revival–style YMCA building into a 173-room hotel and museum.
In the rooms and suites you’ll find 21c’s signature modernist style, a look that’s stylish enough for design fans but straightforward enough for traditional luxury-hotel guests. Every unit, naturall, comes with its own piece of original art, and all feature upscale details like 50-inch televisions and Malin+Goetz bath products.
They’re among the finest lodgings in town, but 21c doesn’t stop there. Woven throughout the building is 14,000 square feet of exhibition space, and the building’s former life as a YMCA means it already had space for a full-scale athletic club, including an indoor pool and even a running track. The restaurant, Idol Wolf, is inspired by the Spanish tapas tradition, and the Good Press café serves coffee by local St. Louis roasters.
The Ritz Carlton
5-Star Hotel
The appeal of staying in a chain hotel, any chain, is a certain consistency, an ability to know what one can expect in advance. If you are visiting a place like Milan, New York, or Tokyo, you may prefer to be surprised by the seemingly endless variety of hotels; you may welcome the unexpected and relish the satisfaction of seeing how different hotels find unique solutions to the same basic hospitality puzzle — how to make their guests happy.
But in a city where one's lodging options are constrained, a city with no market for independent, adventurous boutique hotels, the consistency of a chain hotel is a welcome guarantee. And few hotel chains manage to turn consistency into an advantage quite as well as Ritz-Carlton.
Thus, the Ritz-Carlton St. Louis draws strengths from the brand's basic template, yet without that “where am I again?” feeling so common to bland corporate chains. Here the familiar drawing-room atmosphere of the wood-paneled old-world lobby is a welcome immersion into a world of luxury seemingly foreign to the upscale suburb this hotel calls home.
Thus, it's almost like a vacation within a vacation — inside this hotel, you are no longer in St. Louis, but in some sort of Democratic Republic of Ritz-Carlton, a place where all bathrooms are marble and the Cigar Bar is the obvious nightlife choice. And this particular outpost has its own distinct personality — dinner is served not just inthe traditional fine dining restaurant but in the Wine Room as well, with the food chosen to complement the wines, rather than the other way round — and this must take some choosing, as this hotel boasts the most extensive wine list of any Ritz-Carlton anywhere.
Things to do in St. Louis:
Gateway Arch – The world’s tallest arch, standing at 630 feet, offering panoramic views of the city.
Missouri Botanical Garden – A beautiful garden featuring seasonal blooms, historic architecture, and educational exhibits.
Saint Louis Art Museum – A fantastic museum showcasing art collections spanning thousands of years.
City Museum – A whimsical, interactive museum featuring slides, tunnels, and repurposed architectural elements.
Saint Louis Zoo – A world-class zoo with thousands of animals and free admission. Citygarden – A sculpture park featuring interactive fountains and modern art installations.
The Fabulous Fox Theatre – A stunning 1929 theater, hosting Broadway shows and concerts.
Busch Stadium – Catch a St. Louis Cardinals baseball game in a lively atmosphere
Union Station & St. Louis Aquarium – Explore interactive exhibits, a Ferris wheel, and a historic train station.
Anheuser-Busch Brewery Tour – Learn about beer-making history and see the famous Budweiser Clydesdales
Days 7 - 8: Drive to Springfield, Missouri
(about 3.5 hour's drive)
Springfield, Missouri, is known as the birthplace of Route 66, making it a must-visit stop for road trippers exploring the Mother Road. The city is packed with historic landmarks, quirky roadside attractions, and nostalgic Route 66 experiences.
Things to see on route to Springfield:
Missouri Civil War Museum – A 22,000-square-foot museum at Jefferson Barracks Historic Site, offering deep insights into Civil War history.
Scott Joplin House State Historic Site – A museum dedicated to the "King of Ragtime," featuring exhibits on Scott Joplin’s life and music.
Cahokia Mounds State Historic Site – A UNESCO World Heritage Site showcasing ancient Native American history and impressive earthen mounds.
Concordia Historical Institute – A museum preserving Lutheran history, with exhibits on religious heritage and artifacts.
Bellefontaine Cemetery & Arboretum – A historic cemetery with stunning architecture and a rich cultural past.
Route 66 State Park – A nostalgic stop featuring a visitor center with Route 66 memorabilia and scenic walking trails.
Ted Drewes Frozen Custard – A legendary Route 66 treat famous for its thick, delicious frozen custard.
Meramec Caverns – A massive cave system with fascinating formations and a history tied to Jesse James.
Where to stay in Springfield:
Culture Boutique Hotel
3-Star Hotel
A boutique hotel with six rooms available for overnight stay, each inspired by a city in Eurasia. The rooms feature furniture made from reclaimed materials from our own building, whose resume has read opera house, drug store, and mattress factory, among others. The rooms vary in both price and proportion, but aesthetics, comfort and function manifest throughout.
Bass Pro Shops Angler's Lodge
2.5 Star Hotel
Centrally located in Springfield, Missouri, Angler's Lodge is convenient, affordable, and pet-friendly. You'll find interactive experiences just steps away at the award-winning Johnny Morris' Wonders of Wildlife National Museum & Aquarium along with an exciting trip through the #1 Tourist Attraction in the state of Missouri - The Grandaddy Bass Pro Shops Outdoor World. During your stay, you'll enjoy a complimentary breakfast, an indoor pool and more.
Hotel Vandivort
4-Star Hotel
Hotel Vandivort is the first of its kind, a boutique hotel in Springfield, Missouri providing an inspiring, community-centric experience for locals and travelers alike. Hotel Vandivort's unique rooms span two buildings: Historic, a repurposed, century-old structure that was once a Masonic Temple; and V2, which sits just steps away from the original building. From rooftop dining at Vantage to the sophisticated yet approachable atmosphere of The Order, or simply dining in your suite, you'll find something to suit your mood and your taste buds.
Things to do in Springfield:
Fantastic Caverns – A fascinating drive-through cave tour showcasing stunning rock formations.
Mizumoto Japanese Stroll Garden – A peaceful, beautifully landscaped garden perfect for relaxation.
Wonders of Wildlife National Museum & Aquarium – An immersive wildlife experience featuring marine life and conservation exhibits.
Dickerson Park Zoo – A family-friendly zoo with a variety of animals and interactive exhibits.
Springfield Conservation Nature Center – A great spot for hiking and wildlife observation.
Days 8 - 10: Drive to Tulsa, Oklahoma "Capitol of Route 66"
(almost 3 hours' drive time)
Tulsa, Oklahoma, is a thriving city known for its rich history, terrific arts scene, and Route 66 charm. Whether you're exploring museums, outdoor parks, or live music venues, there's plenty to experience!
Things to see on your way to Tulsa:
Route 66 Car Museum (Springfield, MO) – A classic car museum featuring vintage and sports cars, including iconic movie vehicles.
Gay Parita Sinclair Station (Missouri) – A restored 1934 gas station, offering a glimpse into Route 66’s past.
Jasper County Courthouse (Carthage, MO) – A beautiful historic courthouse in the heart of Carthage.
Boots Court Motel (Carthage, MO) – A classic 1939 motel, preserving the vintage charm of Route 66.
Precious Moments Chapel (Carthage, MO) – A unique chapel featuring hand-painted murals and stained glass.
Route 66 Historical Village (Tulsa, OK) – A museum celebrating Route 66’s history, showcasing vintage cars, signage, and interactive exhibits.
Golden Driller Statue (Tulsa, OK) – A giant oil worker statue, symbolizing Tulsa’s oil industry heritage.
Tulsa Route 66 Main Street (Tulsa, OK) – A historic district promoting the preservation of Route 66’s cultural and economic legacy.
Vickery Phillips 66 Station (Tulsa, OK) – A classic Phillips 66 gas station, showcasing Route 66’s vintage charm.
Where to stay in Tulsa:
Hotel Indigo Tulsa DWTN
3-Star Hotel
Hotels like the Hotel Indigo Tulsa Downtown are evidence that, by now, the boutique-hotel revolution is over, having long since been decided in favor of the insurgents. These days even Oklahoma’s second-largest metropolis can boast of a lodging with luxury-boutique swank and high-design good looks. The location, on Santa Fe Square in the vibrant city-center Blue Dome district, could hardly be more auspicious; here you’re surrounded by Tulsa’s finest restaurants, and a short walk from either the Arts District or the historic commercial center.
In the rooms you’ll find what might be a surprisingly urban loft-style look, featuring raw concrete ceilings, hardwood flooring, modernist-inspired furniture, and murals and photographs depicting scenes from Tulsa’s oil-rich history. This is no skyscraper, but neither is the Blue Dome a particularly high-rise district — which means the views of the city’s rooftops are memorable ones.
With the entertainment district just outside, the Indigo doesn’t need to offer all things to all people — one versatile bar and restaurant is all that’s required, and the Prospect Local Bar and Kitchen is up to the task, serving breakfast, lunch, dinner, room service, and drinks.
Harwelden Mansion
3-Star Hotel
Listed on the National Register of Historic Places, Harwelden Mansion sits on one full city block overlooking the Arkansas River. Set in an English Tudor masterpiece, the 1923 architecture, elegant decor, and manicured gardens makes it the perfect retreat for those travelers looking for a unique and luxurious experience.
Ambassador Hotel Tulsa, Autograph Collection
4-Star Hotel
Experience sophisticated style at Ambassador Hotel Tulsa Autograph Collection. This luxury hotel is located inside one of the city's most historic buildings in Tulsa, Oklahoma. Take advantage of complimentary shuttle service and excellent location near BOK Center, Cains Ballroom and Cox Business Center. Reenergize day or night in Tulsa atthe 24-hour fitness center with cardio machines and free weights. When it comes to your business, meet deadlines with three meeting venues comprising 1,676 square feet of space. Dine at The Chalkboard, an American restaurant serving classic dishes and a wide variety of handcrafted cocktails. At the end of the day, retreat to luxury hotel rooms and suites featuring large living areas, plush bedding and workstations with ergonomic chairs. Whether you are in Tulsa Oklahoma for work or pleasure, delight in high-quality hospitality at Ambassador Hotel Tulsa Autograph Collection.
Things to do in Tulsa:
Philbrook Museum of Art – A stunning museum housed in a 1920s Italian-style villa, featuring art collections and beautiful gardens.
Oklahoma Aquarium – Home to thousands of marine creatures, including sharks, jellyfish, and river otters. Tulsa Zoo – A family-friendly zoo with wildlife exhibits and conservation programs.
Gilcrease Museum – A museum showcasing Western art, Native American artifacts, and historical collections.
Cain’s Ballroom – A historic music venue that has hosted legends like Bob Wills and The Sex Pistols.
Guthrie Green – A beautiful urban park in the heart of Tulsa’s Arts District, perfect for picnics and live events.
Tulsa Performing Arts Center – Catch Broadway shows, concerts, and local performances. Route 66 Landmarks – Tulsa is home to several iconic Route 66 attractions, including neon signs, diners, and historic landmarks.
Days 10 - 12: Drive to Oklahoma City, Oklahoma "OKC"
(about 2 hours' drive time)
Oklahoma City is a dynamic city blending Western heritage, modern attractions, and a thriving arts scene. For more on Oklahoma City, see my post: Best Hotels in each State - Part III
Things to see on way to Oklahoma City:
Route 66 Historical Village (Tulsa, OK) – A museum celebrating Route 66’s history, showcasing vintage cars, signage, and interactive exhibits.
Route 66 Dog Park (Tulsa, OK) – A fun stop for travelers with pets, offering a spacious area for dogs to play.
The Outsiders House Museum (Tulsa, OK) – A must-visit for fans of the classic novel and film, preserving the Curtis Brothers’ home.
OK County 66 - John’s Place (Arcadia, OK) – A miniature Route 66 attraction, featuring scaled-down versions of famous landmarks.
Centennial Land Run Monument (Oklahoma City, OK) – A stunning art installation commemorating the Land Run of 1889.
More Road Trip Highlights
Arcadia Round Barn – A historic red barn, one of Route 66’s most famous landmarks.
Pops 66 Soda Ranch – A retro diner and gas station, featuring a 66-foot-tall neon soda bottle.
Seaba Station Motorcycle Museum – A museum showcasing vintage motorcycles and Route 66 memorabilia.
Where to stay in Oklahoma City:
Ambassador Hotel Oklahoma City, Autograph Collection
4-Star Hotel
Ambassador Hotel Oklahoma City, Autograph Collection is the only hotel located in the city's Midtown District, offering easy access to Chesapeake Energy Arena, Cox Convention Center, Bricktown, Zoo Amphitheater and the Oklahoma City Museum of Art.
Omni Oklahoma City Hotel
4-Star Hotel
Omni Oklahoma City Hotel pays homage to the heritage and culinary prowess of the city. With uninterrupted views of Scissortail Park and the downtown skyline, there’s no better place to spend a romantic getaway, business trip or family vacation. This hotel in Oklahoma City offers 605 guest rooms and suites near Bricktown. All are outfitted with modern in-room amenities, including Keurig coffee makers and fast Wi-Fi. Discover six dining destinations that showcase the best cuisine in the city. Relax at the rooftop pool and keep up with workouts in the state-of-the-art fitness center. You can also treat yourself to a soothing facial or massage from Mokara Spa before heading out to Paycom Center, Oklahoma City Convention Center or other nearby venues. Stay in the walkable downtown area, with plenty of things to do nearby. You can also host your next meeting or event at the hotel, with 76,000 square feet of available event space.
Colcord Hotel Oklahoma City, Curio Collection by Hilton
4-Star Hotel
In the heart of downtown Oklahoma City, this historical hotel is directly across from Myriad Botanical Gardens. Paycom Center and Oklahoma City National Memorial & Museum are within walking distance. Enjoy panoramic views over the city from the top of Devon Tower, as well as from our on-site restaurant and 4,950 sq. ft. of event space.
Things to do in Oklahoma City:
Oklahoma City National Memorial & Museum – A powerful tribute to the victims of the 1995 Oklahoma City bombing, offering interactive exhibits and a serene reflection pool.
National Cowboy & Western Heritage Museum – A must-visit for Western culture lovers, featuring art, artifacts, and cowboy history.
Oklahoma Contemporary Museum – A modern art museum showcasing exhibitions, performances, and creative workshops.
Myriad Botanical Gardens – A beautiful urban oasis with walking trails, gardens, and seasonal events.
Bricktown Entertainment District – A lively area with restaurants, bars, and the scenic Bricktown Canal.
Oklahoma City Zoo – Home to hundreds of species, including big cats, elephants, and interactive exhibits.
Riversport Adventures – Try whitewater rafting, zip-lining, and kayaking in the heart of the city.
Factory Obscura – An immersive art experience blending music, visuals, and interactive installations.
Scissortail Park – A beautiful green space perfect for picnics, concerts, and outdoor activities. American Banjo Museum – A one-of-a-kind museum celebrating the history and craftsmanship of banjos.
Day 12 - 14: Drive to Amarillo, Texas "Big Brown Flat"
(about 4 hours' drive time)
Amarillo, Texas, is a lively city known for its Western heritage, Route 66 nostalgia, and stunning landscapes.
Things to see on route to Amarillo:
Route 66 Historic District (Amarillo, TX) – A mile-long stretch of shops, clubs, and restaurants, preserving the spirit of Route 66.
I Am Rt 66 Visitor Center (Amarillo, TX) – A museum dedicated to preserving Route 66’s legacy, featuring art exhibits and unique souvenirs.
The Big Texan Steak Ranch (Amarillo, TX) – Famous for its 72-ounce steak challenge—if you eat it all, it’s free
Midpoint Café (Adrian, TX) – Located at the exact midpoint of Route 66, offering delicious pies and a nostalgic atmosphere.
Boots Court Motel (Carthage, MO) – A classic 1939 motel, preserving the vintage charm of Route 66.
Tower Station & U-Drop Inn Café (Shamrock, TX) – One of Route 66’s most recognizable historic buildings, built in 1936.
Devil’s Rope Museum (McLean, TX) – A unique museum dedicated to barbed wire history, showcasing its impact on the American West.
Bill’s Backyard Classics (Amarillo, TX) – A private automobile museum featuring 100+ classic, custom, and hot rod vehicles.
Where to stay in Amarillo:
The Cactus Cove Inn and Suites
2.5 Star Hotel
This newly renovated atmosphere keeps Amarillo’s rich history and architecture in mind while offering modern updates that guests will enjoy. Escape into a peaceful oasis where Texas charm meets relaxation. Come stay in our deluxe king suite or double queen overlooking the atrium. Each room includes a cloud mattress, kitchenette, and mini bar.
Drury Inn & Suites
3-Star Hotel
Drury Inn & Suites Amarillo is 10 minutes west of downtown Amarillo off I-40. This area is known as the medical district, but there’s plenty of shopping, dining, golfing and entertainment nearby! Relax in clean, comfortable rooms and enjoy free hot breakfast every morning and free hot food and cold beverages every evening at the 5:30 Kickback®.
The Barfield, Autograph Collection
4-Star Hotel
The Barfield, Autograph Collection is a luxury hotel that embodies the heritage and culture of the Texas Panhandle. Perfectly positioned in the heart of downtown Amarillo, The Barfield is one of the city's first luxury boutique hotels. The hotel is located on iconic Polk Street near local shops and restaurants, plus attractions like the Amarillo Zoo. This hotel treats travelers and locals alike to timeless elegance and classic cattle-culture charm. Sip premium cocktails at the Paramount Recreation Club, a Prohibition-era speakeasy, or savor delicious steakhouse fare at the on-site Italian restaurant. After a workout in the 24-hour fitness center, retire to a luxury hotel room with West Texas-inspired décor, blackout curtains and decadent bedding. Downtown Amarillo has rarely experienced luxury quite like this. With premium hotel accommodations, exquisite service and an always-welcoming atmosphere, The Barfield, Autograph Collection seeks to transcend your expectations.
Things to do in Amarillo:
Cadillac Ranch – One of the most famous roadside attractions, featuring half-buried Cadillacs covered in graffiti.
Wonderland Amusement Park – A family-friendly amusement park with rides, games, and entertainment.
Amarillo Museum of Art – A fantastic art museum featuring permanent and rotating exhibits. American Quarter Horse Hall of Fame & Museum – A must-visit for horse lovers, showcasing the history and impact of the American Quarter Horse.
Palo Duro Canyon State Park – The second-largest canyon in the U.S., offering hiking, camping, and breathtaking views.
Helium Time Columns Monument – A unique monument celebrating Amarillo’s role in helium production.
Kwahadi Museum of the American Indian – A museum showcasing Native American art, culture, and performances.
Days 14 - 16: Albuquerque, New Mexico "ABQ"
Albuquerque, New Mexico, is a lively city celebrated for its deep history, varied culture, and breathtaking scenery. Whether you're wandering through the historic Old Town, taking a hot air balloon ride, or indulging in Southwestern cuisine, there's a lot to enjoy! For more on Albuquerque, see my post: Ultimate Road Trip: National Parks Part I
Things to see on way to Albuquerque:
West Central Route 66 Visitor Center – A great stop to learn about Route 66 history and explore local attractions.
Telephone Museum of New Mexico – A unique museum showcasing the evolution of telecommunication in New Mexico.
NM Route 66 Association – A hub for Route 66 enthusiasts, offering historical insights and memorabilia.
Route 66 Crossing Sign – A classic Route 66 landmark in Albuquerque, perfect for a nostalgic photo op.
KiMo Theater – A historic Pueblo Deco-style theater, hosting performances and events. Petroglyph National Monument – Explore ancient rock carvings created by Indigenous peoples and Spanish settlers.
Sandia Peak Aerial Tramway – Ride one of the longest aerial tramways in the world for breathtaking views of Albuquerque.
Ghost Towns & Abandoned Motels – Explore forgotten towns that once thrived along the highway.
Where to stay in Albuquerque:
Hotel Albuquerque at Old Town
3-Star Hotel
Our landmark Albuquerque luxury hotel is conveniently located in the heart of Old Town and the Sawmill District, offering accommodations and amenities, including an on-site restaurant and bars, an outdoor resort swimming pool, a romantic wedding chapel, and more than 62,000 square feet of indoor and outdoor meeting and event space.
Hotel Albuquerque is only steps away from Sawmill Market: a 25,000 square-foot food hall with various local vendors featuring an array of culinary experiences.
Sandia Resort & Casino
4-Star Resort
Overlooking the majestic Sandia Mountains, just minutes from Albuquerque Sunport, Sandia Resort & Casino welcomes guests to a unique Southwestern setting with outstanding service and modern comforts. Upon your arrival, you will be greeted by our distinctive porte-cochère entry and magnificent grand lobby, which boasts stunning mountain views along with original photographs and artwork that celebrates the region’s rich pueblo heritage.
Every guest room and suite at Sandia Resort & Casino was designed with your comfort in mind. Colorful Southwestern furnishings, flat-screen televisions and luxurious bathrooms with walk-in showers and separate soaking tubs are just the beginning. From deluxe rooms to the grandeur of the Super Suite, the premier Albuquerque accommodations offer the perfect setting to unwind between games or enjoy a relaxing New Mexico vacation.
The spectacular outdoor Amphitheater can seat over 4,000 guests and frequently features some of today’s top musical acts under a canopy of stars. Laying a pathway to stillness and peace, the Green Reed Spa transforms the ordinary. Inspired by the subtle, profound abundance of the high desert – brilliant blue skies, healing native plants, and unmistakable spirit – discover, immerse, experience, and transform. Situated at the base of the Sandia Mountains with expansive views of the river valley below, discover the Green Reed Spa’s serenity and luxury unlike anything else in New Mexico.
Hotel Chaco
4-Star Hotel
Hotel Chaco is honored to be included as a winner in the 2023 Sunset Travel Awards “Where to Stay: Best City Stays” for travel in the West.
Situated in the heart of Albuquerque in the Historic Old Town and new urban Sawmill districts, Hotel Chaco is a AAA 4 diamond boutique hotel in Albuquerque that beckons luxury travelers seeking authentic experiences. Hotel Chaco is the most distinct hotel in all of New Mexico. The unique room layouts are designed by world-famous architecture firm Gensler and feature authentic interior design with the best collection of contemporary Native American New Mexican artists on display. Hotel Chaco’s pale stone masonry facade and wooden accents are designed to work with the warm, dry climate of the Southwest and are reminiscent of architectural elements found at Chaco Canyon and in New Mexico’s Pueblos.
Award-winning interior designer Kris Lajeskie conceived Hotel Chaco’s interiors using subdued hues inspired by the natural wool variations employed by Navajo weavers. The hotel’s interiors juxtapose ancestral references with contemporary materials, furnishings, and original artwork. Hotel Chaco celebrates local and regional artists throughout all public spaces and then pursues the same art sensibility in guestrooms and landscape design. You can explore and purchase your own masterpieces from many of these artists at Gallery Hózhó.
Things to do in Albuquerque:
Indian Pueblo Cultural Center – A must-visit museum showcasing Native American history, art, and traditions.
Albuquerque Museum – A fantastic museum featuring art, history, and cultural exhibits.
Old Town Albuquerque – Stroll through historic adobe buildings, charming shops, and local restaurants.
ABQ BioPark – A zoo, aquarium, and botanical garden, perfect for families and nature lovers.
National Hispanic Cultural Center – A hub for Hispanic arts, performances, and cultural events.
Unique Experiences
Open Space Visitor Center – Explore nature trails, wetlands, and stunning views of the Sandia Mountains.
Balloon Fiesta Park – Visit the site of the world-famous Albuquerque International Balloon Fiesta.
Days 16-17: Drive to Flagstaff, Arizona "The Staff"
(about 5-hours' drive time)
Flagstaff, Arizona, is a must-visit stop along Route 66, offering a mix of historic charm, stunning landscapes, and vibrant culture. Whether you're cruising the Mother Road, exploring national parks, or soaking in the local history
, Flagstaff has plenty to offer.
Things to see on route to Flagstaff:
Route 66 Crossing Sign – A classic Route 66 landmark in Albuquerque, perfect for a nostalgic photo op.
Historic Downtown and Railroad District – Stop by the Flagstaff Visitor Center, located in a historic train station, for maps and travel tips.
Laguna Pueblo – A historic pueblo dating back to the 1400s, offering a glimpse into Native American culture.
New Mexico Mining Museum – Learn about the mining boom that shaped the region, including uranium discoveries.
Bandera Volcano & Ice Cave – A privately owned lava cave with stunning green ice formations.
El Morro National Monument – See centuries-old inscriptions left by Spanish explorers and Indigenous travelers.
Painted Desert & Petrified Forest National Park – A breathtaking landscape filled with colorful rock formations and ancient petrified wood.
Harvey House Museum – A historic railroad stop showcasing Fred Harvey’s hospitality empire.
Meteor Crater Natural Landmark – Visit one of the best-preserved meteor impact sites in the world.
Walnut Canyon National Monument – Explore ancient cliff dwellings built by the Sinagua people.
Where to stay in Flagstaff:
Americana Motor Hotel
3-Star Hotel
Driving down Route 66 you’ll find a nostalgic, playful retreat where the allure of hitting the open road meets outdoor thrills under wide-open skies. This is where lawn games by a fire pit and heated-pool swims happen year-round. Where bikes are available and you can pop a top on a cold can in the Backyard. Whether you’re on a fresh-air escape to hike under clear skies, planning a family ski trip, or driving in to see the Grand Canyon and experience legendary stargazing, the award-winning Americana Motor Hotel offers everything you need for the next stage of your journey.
High Country Motor Lodge
4-Star Hotel
A classic mid-century motor inn on Route 66 in Flagstaff, Arizona has found new life as the High Country Motor Lodge, and as motel restorations go, it’s a very thorough one — it’s stylish both inside and out, and its rooms retain none of the mass-produces aesthetic that marked the original motel era. Instead, you’ll find swanky beds with vintage-style blankets, modern bathrooms with quality products, and, in a quirky retro touch, tape decks complete with mix tapes. There’s a Nordic-style spa — meaning a sauna, a hot tub, and a cool shower, for alternating warm and cold — and the General Store is actually a restaurant, serving a made-to-order breakfast as well as sandwiches, salads, and Roman-style pizza.
Bespoke Inn Flagstaff
4-Star Hotel
Bespoke Inn Flagstaff is a fully renovated 1894 property that combines historic charm and modern amenities, located in the heart of downtown. Guests can enjoy an elevated experience with luxury Flagstaff accommodations, attentive hospitality, and amenities curated for the Bespoke brand. Stay in newly appointed rooms and suites, all with private bathrooms, some with fireplaces, A/C, and smart TVs. Enjoy the convenience of being within walking distance to historic downtown shops and restaurants or dine at the adjacent farm-to-table restaurant, Brix, one of Flagstaff’s best.
Things to do in Flagstaff:
Riordan Mansion State Historic Park – A beautiful 1904 mansion showcasing Flagstaff’s lumber industry history.
Walnut Canyon National Monument – Explore ancient cliff dwellings built by the Sinagua people.
Wupatki National Monument – Discover prehistoric pueblos and stunning desert landscapes. Museum of Northern Arizona – A fascinating museum celebrating the Colorado Plateau’s history and culture.
Arizona Snowbowl – A popular ski resort offering winter sports and scenic summer hikes.
Lowell Observatory – Visit the place where Pluto was discovered and enjoy stargazing events. Sunset Crater Volcano National Monument – Walk through lava fields from an eruption 1,000 years ago.
Route 66 Landmarks – Flagstaff is packed with retro diners, neon signs, and historic motels. Coconino National Forest – A stunning forest with hiking, camping, and scenic drives.
Days 17-19: Drive to Lake Havasu City, Arizona "LHC"
(about 3.5 hours' drive time)
Lake Havasu City, Arizona, is a desert oasis known for its stunning lake views, outdoor adventures, and iconic London Bridge.
Things to do in route to Lake Havasu City
Historic Downtown and Railroad District – Stop by the Flagstaff Visitor Center, located in a historic train station, for maps and travel tips.
Picture Canyon Trailhead – A beautiful nature preserve featuring petroglyphs, wildlife, and scenic hiking trails.
Riordan Mansion State Historic Park – A stunning 1904 mansion showcasing Flagstaff’s lumber industry history.
Oak Creek Canyon – A scenic drive with breathtaking views, perfect for a quick stop. Williams, AZ – A classic Route 66 town with retro diners, neon signs, and the Grand Canyon Railway.
Delgadillo’s Snow Cap Drive-In (Seligman, AZ) – A quirky roadside diner famous for its Route 66 nostalgia and playful humor.
Hackberry General Store (Kingman, AZ) – A historic Route 66 stop filled with vintage memorabilia and classic cars.
Cattail Cove State Park – A beautiful waterfront park near Lake Havasu, perfect for boating, fishing, and hiking.
Where to stay in Lake Havasu City:
The Nautical Beachfront Resort
3-Star Hotel
Set along Lake Havasu City’s sandy beaches, The Nautical Beachfront Resort offers guests an authentic laid-back experience with the lively vibe of the Caribbean. The blue green water of Lake Havasu is just steps away, where the fun never ends. With the only private boat launch ramp in the region, The Nautical Beachfront Resort is the premier choice for all watercraft enthusiasts.
Heat Hotel
3-Star Hotel
Heat Hotel is a white-hot boutique hotel on the shores of Lake Havasu with unparalleled water and London Bridge views. Enjoy luxe room amenities and 4,000 square feet of celebration under the sun at this lakefront lounge. Relax, renew, revive.
London Bridge Resort
3-Star Hotel
Among Lake Havasu City hotels, no destination combines comfort, affordability, and amenities like London Bridge Resort. All 122 of the studio, one-, and two-bedroom suites boast spacious living areas, and offer nine distinctive options to meet any need.
Stretch out and enjoy amenities including a fully equipped kitchenette, free Wi-Fi access, and flat-screen TVs with DVD players. Some suites also feature private balconies. Choose one of our spacious Bridgeview Suites for scenic views of London Bridge and the hotel pools.
Find all of the comforts of home, without all of the inconveniences of cleaning fees, having to park your boat and launch daily, and having to drive to town for entertainment. London Bridge Resort offers direct access to the best entertainment and dining in Lake Havasu, boat docks, and secured parking as well as access to everything you need within a few steps of your resort suite condo overlooking the Bridgewater Channel.
Things to do in Lake Havasu City:
London Bridge – Originally built in 1830s London, this famous bridge was relocated to Arizona in the 1960s, making it one of the city's most iconic landmarks.
Lake Havasu State Park – A beautiful waterfront park with beaches, hiking trails, and boat ramps.
Boating & Water Sports – Enjoy jet skiing, wakeboarding, paddleboarding, and scenic boat tours on the lake.
Havasu National Wildlife Refuge – A protected area perfect for birdwatching and nature walks.
Lake Havasu Golf Club – Play a round of golf with breathtaking lake views.
Relax on the sandy beaches – Lake Havasu offers secluded coves and lively waterfront spots. English Village – A charming area near London Bridge with shops, restaurants, and scenic views.
Off-Road Adventures – Explore desert trails and rugged landscapes on an ATV or Jeep.
Days 19-21: Drive to Santa Monica, California "SaMo"
(about 5.5 hours' drive)
Santa Monica, California, marks the official end of the legendary Route 66, making it a must-visit destination for road trippers completing their journey along the Mother Road. The route takes you through deserts, mountains, and historic towns, culminating in the beautiful beaches of Santa Monica.
Things to see on route to Santa Monica:
Mojave National Preserve – A stunning desert landscape with sand dunes, volcanic cinder cones, and Joshua trees.
Amboy & Roy’s Motel Café – A classic Route 66 stop, featuring a historic motel and vintage gas station.
Barstow Route 66 Museum – A fascinating museum showcasing Route 66 memorabilia and history.
San Bernardino & Pasadena – Drive through historic towns, including San Bernardino, home to the first McDonald's restaurant.
Santa Monica Pier – The official end of Route 66, marked by the "End of the Trail" sign, offering stunning ocean views and classic boardwalk attractions.
Pacific Park – Located on the Santa Monica Pier, this amusement park features thrilling rides, including the solar-powered Ferris wheel.
Route 66 End of the Trail Sign – A must-see landmark marking the final stop of Route 66.
The Cove Skatepark – A popular skate park featuring three bowls and a street section.
Santa Monica Stairs – A hidden gem offering a great workout with scenic views.
Where to stay in Santa Monica:
The Ambrose Hotel
3-Star Hotel
While at The Ambrose, you’ll find yourself in the best of all worlds: This thoughtfully designed hotel is located in a serene residential area yet is close to premier Santa Monica attractions. A stay here feels tailored to you, thanks to attentive service and amenities essential to a perfect stay—like house car service, bicycles, and more. Delightful common spaces, filled with plants and inviting seating, can rightfully be considered an amenity in themselves. It’s all intentionally crafted to create a sense of revitalization.
The Pierside Santa Monica
4-Star Hotel
First-time visitors to Santa Monica may occasionally be surprised to find it a bit less laid-back and bohemian than they expect. The Pierside Santa Monica sets out to fix all that. This isn’t just the first luxury boutique hotel to open in Santa Monica in quite some time, but its address on Colorado Avenue at Ocean Avenue makes it the closest one to the iconic Santa Monica pier — a victory for anyone who’s a stickler for truth in hotel names.
What’s inside is a hotel that’s modern and visually surprising, but true to its Southern California inspiration, incorporating a wide range of influences from Arts & Crafts and surf culture to mid-century Modernism and some handsome custom-designed contemporary furniture. The most impressive rooms are perhaps the ones with views of the pier and the Pacific Ocean, though there isn’t a substandard one in the house.
The Board Shop is what it sounds like and more: a place to rent a surfboard, some beach chairs, or even a ukulele or a Nintendo Switch. Meanwhile the Surfing Fox is the Pierside Santa Monica’s coastal Californian restaurant and bar.
Shutters on the Beach
5-Star Hotel
We’re accustomed to viewing the hospitality world through a critical lens, but every now and then a hotel lives up to the fantasy, and then some. Shutters on the Beach is exactly what you would want a Santa Monica luxury hotel to be, if you were designing it from a blank page. And the best part about it is that you don’t have to — it actually exists, and Michael S. Smith has already gone to the trouble of designing it, in a style that combines the barefoot ease of the West Coast with just a bit of Northeast elegance.
It’s a glamorous backdrop for what is often a glamorous crowd, but the vibe is thoroughly relaxing. Shutters opens right onto the beach, which is more rare than you might imagine around here, and the result is an exceedingly private atmosphere. The rooms are as luxe as can be, and a great many of them have ocean views, including all the suites — and in defiance of the SoCal stereotype your room comes equipped with a small personal library, in addition to all the usual comforts.
And the comforts continue beyond the accommodations: the hotel’s ONE Spa is first-rate, and its restaurants are impressive as well, from the refined 1 Pico to the more casual Coast and the multi-purpose Living Room lounge. The service is stellar, the amenities are thoughtful, the setting is idyllic, and the concept is perfectly realized — sometimes the classics are classics for a reason.
Things to do in Santa Monica:
Santa Monica Pier – The heart of the city, featuring Pacific Park amusement rides, street performers, and stunning ocean views.
Santa Monica State Beach – A 3.5-mile stretch of sandy coastline, perfect for swimming, surfing, and sunbathing.
La Brea Tar Pits and Museum – A fascinating prehistoric site showcasing fossils of Ice Age creatures.
The Getty Villa – A stunning museum featuring ancient Greek and Roman art in a breathtaking setting.
Venice Canal Historic District – A hidden gem offering scenic canals, charming bridges, and peaceful walks.
Pacific Park – Ride the solar-powered Ferris wheel for panoramic views of the coastline. Marvin Braude Bike Trail – A 22-mile scenic path stretching from Santa Monica to Torrance Beach.
Third Street Promenade – A pedestrian-friendly shopping and entertainment district with live music and street performers.
Palisades Park – A bluff-top park offering breathtaking sunset views over the Pacific Ocean.
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