Legendary Route 66 was once the primary route between Chicago and Los Angeles. Today, it offers a classic road trip for taking in some of the country’s most iconic sites along the over 2,200-mile-long stretch. There are countless attractions, many of which are rather quirky, like Cadillac Ranch with its half-buried Cadillacs that are nose-first in the ground, but they range from diners and murals to museums. Along the way, you’ll find a variety of accommodation options, including some fabulous vacation rentals and retro hotels to help you get or stay in the mood – you might want to turn up the tunes like Nat King Cole’s (Get Your Kicks on) Route 66 too.
The Langham - Chicago, Illinois
Kick off your trip right in Chicago by staying at The Langham, which offers beautiful lake, river, and Magnificent Mile views from floor-to-ceiling windows, along with a gorgeous indoor pool, a spa, a fitness center, and a highly-acclaimed restaurant. While you’re here, you might do some shopping for your trip along the Magnificent Mile or explore the Art Institute of Chicago with one of the finest collections of Impressionist paintings you’ll find anywhere, along with remarkable works from masters like Picasso. Before leaving, be sure to have breakfast at Lou Mitchell’s. A Chicago institution since 1923, it’s famous for providing delicious meals to travelers before they hit historic Route 66.
Lucky 7s Bungalow with Hot Tub - Pontiac, Illinois
Pontiac is home to the Route 66 Association Hall of Fame & Museum, a must-stop on any Route 66 road trip with thousands of memorabilia items from the glory days of the road. You won’t want to miss the chance to capture a photo of your own vehicle in front of the largest Route 66 shield mural either. Enjoy a memorable stay here by booking the Lucky 7s Bungalow. It sleeps up to five in two bedrooms, both of which have 42″ flat-screen TVs with Roku. There’s a 65″ flat-screen TV with Roku in the living room, and you’ll have a fully stocked kitchen too. The highlight is in the private backyard: a hot tub.
1902 House & Garden - Private Safe Parking - St. Louis, Missouri
St. Louis is an old Route 66 town home to the Gateway Arch, the city’s iconic symbol marking the spot where Lewis and Clark set out on their historic expedition – ride the elevator 630 feet to the observation deck at the arch’s highest point for a bird’s-eye view. Afterward, relax in this 1902 House & Garden rental which provides private, safe parking for your vehicle and sleeps up to four. The beautifully restored, historic home comes complete with an expansive flagstone patio that’s great for unwinding in, with a fountain and picnic table, while the backyard includes a fire pit and more sitting for gathering under the stars.
Munger Moss Motel - Lebanon, Missouri
Lebanon is known as the “Route 66 Mural City” – you can’t drive Route 66 and not admire the murals here, it’s an essential stop as the largest town between Rolla and Springfield, Missouri, and it’s home to the classic Munger Moss Motel. Originally a sandwich shop in Devil’s Elbow, it moved to Lebanon in 1946 with the highway’s modification. To take advantage of the new location, it was turned into a motel. Staying here today, you’ll enjoy a stay in a classic “mom and pop” motel owned and managed by Bob and Ramona Lehman since 1971, a couple inducted into the Laclede County Route 66 Wall of Fame for promoting the route. The rooms are all themed and filled with memorabilia. Plus, you’ll be able to see some of the old businesses along the route, including a Texaco service station.
Boots Court Motel - Carthage, Missouri
Carthage is a quintessential Route 66 town that still retains many places that helped make the route what it was, including the Boots Court Motel. Built-in art deco and streamlined modern style in 1939, it’s one of the oldest and few motels that are still in operation along Route 66. Arthur and Ilda Boots originally advertised “a radio in every room” and offered just four units. While it’s nearly gone under multiple times, it’s been expanded and remodeled over the years to save it from demolition, including a recent renovation with historical accuracy. The affordable rooms are clean and comfortable, with all the modern amenities like air conditioning and Wi-Fi.
Stylish 2 Bedroom Bungalow Close to River Parks - Tulsa, Oklahoma
Just before you reach Tulsa, make a quick stop to see the famous blue whale, which was once in a pond part of a small water park. It’s a Route 66 icon you’ll want to capture a photo of. Just 15 miles further, you’ll be in the birthplace of Cyrus Avery, the “Father of Route 66.” He created the route and was responsible for it getting paved and promoted. The downtown area offers many art deco-style buildings, and you can also visit one of the route’s “mystery points,” the “Center of the Universe” where the echo of your voice comes back to you with more volume and power than what you spoke originally. This stylish 1946 bungalow offers period furnishings and decor, providing the ideal place to stay for up to four guests, complete with a patio and outdoor games like Bocce ball, as well as a Smart TV, Bluetooth sound system, and all the essentials.
Historical Cottage on Route 66 - Clinton, Oklahoma
Clinton is home to a Route 66 Museum that chronicles the stretch of the Mother Road that bisects Oklahoma, complete with a cherry red ’57 Chevy in the window and the chance to walk the “Main Street of America,” which reveals information on places along the route that no longer exists. The Historical Cottage on Route 66 is a two-bedroom for four, with each bedroom featuring a Smart TV, and there’s another one in the main living area. It’s just a mile from downtown, close to the Route 66 museum, and there’s an 18-hole golf course right next door. A barn and private garage provide a safe spot for your vehicle.
Big Texan Motel - Amarillo, Texas
The largest city between Oklahoma City and Albuquerque, Amarillo is an important stop for a couple of reasons. Before entering, you’ll see the massive Big Texan Steak Ranch sign that invites diners to order and finish a 72-ounce steak at the famously kitschy restaurant. It’s part of a complex that includes the Big Texan Motel, a 1950s-style property with a facade that makes it look like it’s in a Wild West town. The rooms have bathrooms with saloon doors, and the swimming pool is shaped just like the state it’s in. After your stay, be sure to visit Cadillac Ranch, a public art installation created by hippie/artists made up of graffiti-covered Cadillac tail fins that are buried at the same angle as the Great Pyramid, standing as a tribute to the American Dream.
Turquoise Trail-er with Sunsets and llamas Too - Santa Fe, New Mexico
Founded in 1607, the beautiful city of Santa Fe is the nation’s second-oldest capital city and a stunning jewel in the Southwest. With so much to see a do, it’s the perfect place for taking a break from driving, enjoying a few days of relaxation, and exploring sites like the 1610 Governor’s Palace, the oldest public building in the U.S. that’s remained occupied. You probably won’t find a better space to park yourself than the Turquoise Trail-er, which perfectly complements your road trip as an authentic, vintage 1971 travel trailer. It has a private shaded deck with mountain views where you can watch the sun go down too.
El Vado Motel - Albuquerque, New Mexico
Albuquerque hosts the longest urban stretch of the “Mother Road,” with lots of old-school diners, carhops, and retro motels with classic neon lights. The El Vado Motel sits in a 1937 building and is one of the highest-rated retro hotels along the route, with lots of historic character and charm, along with all the modern comforts. Half of the rooms were turned into local boutiques and food pods, providing guests with lots of dining and shopping options. There are 22 available, all of which feature mid-century modern furniture and an original art piece made from doors that were repurposed from the original property. They’re the typical historic motor court hotel size, but you can get more space with a separate bedroom and sitting area by booking one of the suites named after classic cars. The old parking lot was transformed into a hotel pool that incorporates the former parking medians.
Wigwam Motel - Holbrook, Arizona
Soon after crossing the border into Arizona, you’ll reach Holbrook, a popular tourist destination for many on a classic road trip. It’s home to the Petrified Forest National Park, with its 250 million-year-old fossilized logs with colorful hues in shades of purple, red, blue, and amber that are up to six feet in diameter. But what Holbrook stands out most for is the Wigwam Motel, the town’s most photographed site. As it’s so popular, you’ll want to book before heading out on Route 66, but your reward for the effort will be an unforgettable stay in a Wigwam with original furnishings. The hotel also has a great classic car display.
Red Garter Inn - Williams, Arizona
Williams isn’t just a gateway to the Grand Canyon, it’s right along Route 66, complete with old-fashioned street lamps, and every other store sells a variety of Route 66 memorabilia. It’s home to the famous Red Garter Inn that’s sure to make for a memorable stay while enjoying the character of the town. It sits within a restored 1897 saloon and bordello with original skylights in the historic district and offers rooms in Old West style with features that can include antique brass beds and clawfoot tubs.
El Trovatore Motel - Kingman, Arizona
Kingman is home to the Historic Route 66 Museum, which was created to preserve the city’s history along the famous route. It includes dioramas, vintage cars, and a film that tells the story of the route from prehistory to the present. While you’re here, stay in the iconic El Trovatore Motel. Built-in 1939, it’s a classic with 100-foot-long neon signs and rooms with individual Hollywood iconic themes. While they’ve retained the original architectural features, all come with modern amenities like cable TVs, free Wi-Fi, microwaves, and mini-fridges.
Quality Inn on Historic Route 66 - Barstow, California
There aren’t a whole lot of accommodation options in Barstow, but it’s a perfect last stop before you reach the end of Route 66, about 130 miles away. It’s home to the Mother Road Museum, which sits in a train station and offers a number of interesting exhibits along with several train cars. The Quality Inn on Historic Route 66 includes a picnic area with BBQ grills and an outdoor pool. There’s also a restaurant and lounge on-site with a complimentary breakfast provided every morning, along with guest laundry facilities.
Shutters On The Beach - Santa Monica, California
Your bucket-list road trip concludes in Santa Monica with a sign at the end of the Santa Monica Pier marking the highway’s traditional end. You’ll be in the perfect spot for a celebratory spin on the world’s only solar-powered Ferris wheel and endless stretches of golden sands. Shutters On The Beach is an ideal place to stay and relax for a while. Known for its historic elegance and wide range of upscale amenities, it opens right onto the beach promenade and includes a gorgeous pool.
