The ultimate Route 66 experience begins in the imagination. For more than a century this storied highway has been the road of dreams. Today it is the quintessential American road trip, a living time capsule, and a tangible link to centuries of American history.

Stretching from Chicago to Santa Monica, this iconic highway has been a symbol of the freedom found on the open road for decades. Whether you’re a seasoned road tripper or a Route 66 newbie, exploring its best museums, historic motels, and restaurants is a must.

With that as an introduction, let me share a few of our favorite places. After all, inspiring road trips by telling people where to go is what we do at Jim Hinckley’s America.

Best Route 66 Museums

Route 66 Association Hall of Fame & Museum, Pontiac, Illinois

Located in the heart of Pontiac, this museum is a tribute to the legends of Route 66. With a vast collection of memorabilia, vintage cars, and fascinating exhibits, it offers a nostalgic journey through the history of the Mother Road.

The museum also houses the premier collection of folk artist Bob Waldmire memorabilia and artifacts. This includes his VW bus, a rolling studio and home as well as inspiration for the Filmore character in the animated film Cars.

Oklahoma Route 66 Museum, Clinton, Oklahoma

This museum provides immersive experience with its interactive displays and exhibits. From the 1920s to the present, visitors can explore the evolution of Route 66 in Oklahoma and its impact on American culture.

Acclaimed author Michael Wallis with the distinctive voice made famous as the Sheriff in the movie Cars narrates several exhibits. The museum also features an expansive gift shop that includes books, many signed by the author.

Cahokia State Historic Site, Collinsville, Illinois

This prehistoric Native American site bisected by an alignment of Route 66 offers a fascinating glimpse into the lives of the pre-Columbian Mississippian culture. The site features towering mounds, interpretive trails, and an acclaimed museum that details the history and significance of Cahokia.

This is a UNESCO World Heritage Center. That makes it unique among Route 66 Attraction.

Preserved here is the central section of the largest prehistoric Native American city north of Mexico. Its zenith was between 700 and 1400.

Pecos National Historic Park, New Mexico

Pecos National Historic Park preserves the cultural and natural history of the Upper Pecos Valley.  Visitors can explore natural wonders as well as the remains of the Pecos Pueblo, an early Spanish mission, a Civil War battlefield, and vestiges of the Santa Fe Trail. This makes Pecos a rich educational experience.

The primary attraction at the park is the ruins of Pecos Pueblo, known historically as Cicuye, framed by stunning landscapes.  The pueblo began as a complex of two dozen rock-and-mud villages built in the valley around AD 1100. By the time the Spanish arrived in the valley the pueblo had evolved into a city that was home to at least 2,000 people who lived Within 350 years the Pueblo IV Era Pecos village had grown to house more than 2,000 people in its five-storied complex.

National Route 66 Museum Complex, Elk City, Oklahoma

This comprehensive complex includes several museums including the Old Town Museum, Farm and Ranch Museum, and the Blacksmith Museum. Diverse and interactive exhibits provide an immersive experience that provides the visitor with a detailed understanding of the area’s history. This is intertwined with a history of Route 66.

An afternoon can easily be spent exploring the complex. At the very least, I recommend three hours.

Best Historic Motels and Hotels on Route 66

Blue Swallow Motel, Tucumcari, New Mexico

Step back in time at the Blue Swallow Motel, a quintessential Route 66 landmark. With its neon signs and time capsule decor, this motel offers a nostalgic experience and a glimpse into the golden age of the great American road trip.

Dating to the late 1930s this is one of the most famous motels on Route 66. So, reservations are highly recommended.

Even though the motel has been fully refurbished, and modern amenities were tastefully added, this is a vintage motel.

Plan accordingly. This is not Holiday Inn Express or Mariott. So, some things that we now take for granted such as numerous outlets for charging tablets and phones aren’t as readily available as the modern traveler has come t expect.  

La Posada Hotel, Winslow, Arizona

Originally built in 1930, La Posada Hotel is a masterpiece of Southwestern architecture. And as it once was facing imminent demolition, it is also a shing example of historic preservation.

Restored to its former glory as a Harvey House property, this historic hotel and restaurant offers luxury and charm. It is a perfect stop for travelers seeking comfort and history. And it comes highly recommended from Jim Hinckley’s America.

Americana Motor Hotel, Flagstaff, Arizona

Located in the heart of Flagstaff, this retro-chic hotel offers modern amenities while maintaining its vintage charm. With its nostalgic decor and friendly service, it’s a great spot for travelers exploring Route 66.

Dating to 1962, the recently renovated property is an excellent example of how an historic motel or hotel can be preserved and transformed to meet the needs of the modern traveler. As an example, Flagstaff is easily explored by bicycle as the city has an expansive trail system. So, the motel offers bicycles in the lobby.

Flagstaff is a dark sky city. That makes it ideal for exploring the night sky with a telescope borrowed from the lobby.

Roadrunner Lodge, Tucumcari, New Mexico

With attention to detail this classic motor lodge has been beautifully restored to offer an authentic 1960s experience. But modern amenities were not sacrificed in the process.

Once an abandoned and derelict property, the Route 66 renaissance served as incentive for its restoration. Today it is an award-winning property, and a favorite among Route 66 travelers.

Here is a tip for you. Ask or a tiki themed room. That will ensure a bit of time travel as the impression will be that you have stepped back to a 1960s resort property.

Cactus Inn Motel, McLean, Texas

This historic mid 1950s motel offers clean, comfortable rooms and a touch of Route 66 nostalgia. It’s a perfect stop for those looking for a 1950s Route 66 experience.

As a bonus, the authentic Red River Steakhouse is next door. A superb dinner, amiable host, a pleasant night’s sleep in a time capsule, what could be better?

Wagon Wheel Motel, Cuba, Missouri

One of the oldest continuously operating motels on Route 66, the Wagon Wheel Motel, offers a delightful mix of history and hospitality. Its beautifully restored rooms and vintage vibe make it a must-visit.

The quaint stone cottages in a park like setting blur the line between past and present. The gift shop in the former restaurant adds to the timeless feel of the property.

Nearby there are several restaurants that I can highly recommend. For dinner Weir on 66 in a 1930s gas station and garage rates high on our list of favorite Route 66 restaurants. In the historic heart of Cuba, for a great dinner at Frisco’s Grill & Pub is hard to beat. And for breakfast my suggestion is Shelly’s Route 66 Café or Huddle House.

Best Historic Restaurants on Route 66

Lou Mitchell’s, Chicago, Illinois

Start your Route 66 journey with a hearty breakfast at Lou Mitchell’s, a Chicago institution since the 1920s. Known for its delicious breakfast offerings, coffee, and classic diner fare, this restaurant is a beloved starting point for many Route 66 enthusiasts.

Hi Way Café, Vinita, Oklahoma

Located on the east end of town this charming café is known for its classic American diner fare and friendly atmosphere. It’s a great place to fuel up and enjoy a slice of Route 66 history as well as pie.

You will want a selfie or two to commemorate your visit. I won’t spoil the surprise, but you will see it as soon as you pull into the parking pot. 

Ariston Café, Litchfield, Illinois

The Ariston Café is one of the oldest restaurants on Route 66 in Illinois. A Route 66 odyssey can’t be considered complete without a meal at this revered gem.

Established in 1924, it offers a warm, welcoming atmosphere and a menu full of delicious comfort food. It originally opened in Carlinville, Illinois, but with the realignment of Route 66 the owner relocated his business to Litchfield in the mid-1930s.

Grand Central Market, Los Angeles, California

Located in downtown Los Angeles on Broadway in the heart of the city’s historic theatre district, Grand Central Market is a bustling food court and market that has been serving the community since 1917. With a diverse array of culinary options, it’s a foodie’s paradise, a neon wonderland, and a great stop on your Route 66 journey.

Earl’s Restaurant, Gallup, New Mexico

Earl’s Restaurant offers a taste of local flavor and hospitality. Known for its Native American art and crafts vendors, as well as its hearty meals, this restaurant is a unique and memorable stop.

This is the real deal! The doors at Earl’s opened in 1948. It remains a favorite for locals, and a pleasant surprise for the Route 66 travelers that stumbles upon it in their travels.

Delgadillo’s Snow Cap Drive-In, Seligman, Arizona

This quirky eatery, established in 1953, is a slice of Americana. Known for its playful décor, practical jokes, good food, and friendly service, Delgadillo’s Snow Cap Drive-In serves up delicious burgers, shakes, and a side of Route 66 charm.

This is one of those places that was started as a means to make a living by providing a service to the endless flow of travelers on Route 66. But today it is a rarity, a survivor, a one owner treasure that is a revered landmark.

Join the Adventure with Jim Hinckley’s America

Ready to hit the road and explore the magic of Route 66? Join the adventure with Jim Hinckley’s America and get a dose of road trip inspiration every week on Coffee With Jim, the weekly podcast on Podbean, hosted by author Jim Hinckley.

Whether you’re planning your next journey or simply dreaming of the open road, Jim’s insights, fascinating guests, and inspiring stories will fuel your wanderlust. So, buckle up, tune in, and let the spirit of Route 66 guide you on an unforgettable adventure. Happy trails!