Route 66 is more than a road, it’s a journey through the heart of America. Along the trail, you’ll discover iconic landmarks, hidden gems, and unforgettable roadside attractions that make every mile worth the drive. From historic stops to must-see destinations, explore the places that turn your golf trip into a true Route 66 adventure.
Whether you’re planning your next stop or exploring along the way, these destinations offer the perfect chance to step off the course and into the culture of Route 66. Snap a photo, meet fellow travelers, and take in the sights that have made this highway legendary for generations. Every stop adds another chapter to your journey, so don’t just pass through, experience it.
Official starting point of Historic Route 66 (East Adams Street and South Michigan Avenue). Include a stop at Could Gate (Millennium Park, Buckingham Fountain, or Grant Park) into the adventure.
Historic limestone penitentiary (1858 – 2002). It has an eerie atmosphere with a famous history. Check out the Joliet Historical Museum and Route 66 Welcome Center as well.
Approximately 30ft. tall fiberglass “Muffler Man” statue. One of the most photographed and recognizable roadside attractions on the entire Mother Road.
About a three-minute walk between the two locations. Classic cars staged in different scenes at the museum on Mill St.; Bob Waldmire artifacts (inspired Cars), and memorabilia at the other.
Worlds largest bottle of catsup! (70ft. tall water tower on 100ft. stand) Originally painted in 1949, this icon makes for fun photos.
Tallest monument in the U.S. (630ft.). Ride a tram to the top for incredible views and travel down to the underground museum. One of the top icons of Route 66!
The original Route 66 crossing from Illinois into Missouri. No longer open to automobiles but has pedestrian/bike path. The mile-long stretch over the Mississippi River and vintage signs make for great, historic Route 66 themed photos.
More than 175 species of birds have been viewed at this park. It has trails and Route 66 exhibits to walk through.
One of the oldest stops on the Mother Road (opened in 1933). Guided tours showcase natural formations, underground rivers, stalactites/stalagmites, and a light show.
Home of a scenic, 130ft. long, Marsh arch bridge from 1923. Must stop for elegant photos with historical American design and beauty.
Built in 1928 and billed as the most elaborate theater between Dallas and Kansas City, this theater hosted performers such as Will Rogers, Bing Crosby, Bob Hope, and Cary Grant. After undergoing restorations beginning in 1990, this theater still hosts performers and still showcases its beautiful “Mighty Wurlitzer” pipe organ from 1928.
This artistic outdoor sculpture park features an approximately 90ft. concrete totem pole and 11 carved totems. Just 3.5 miles from Route 66.
A top icon of the Mother Road. This 80ft. long concrete whale was built in the early 1970s by a zoologist as an anniversary gift for his wife. Sitting in a pond, it is one of the most photographed and beloved roadside oddities on the road. You can walk inside of it and around the pond. Makes for really fun photos!
Standing 76ft. tall, with arm resting on an actual oil derrick, this monument has honored oil workers since 1953. Just one mile from the Mother Road, he is the seventh largest statue in the U.S.
Vibrant district to eat, shop and explore while surrounded by Route 66 statues such as Buck Atom, Stella Atom, Meadow Gold Mack, Rosie the Riveter and Cowboy Bob, all standing approximately 20ft. tall. Explore this stretch of the city, with plenty of photo ops and revitalized signage.
66-foot neon soda bottle sign, over 700 varieties of soda/pop for sale, a diner with burgers and shakes, in a retro environment…what is there not to love? Also check out the Round Barn while in Arcadia.
One of the best (and largest) Route 66 museums anywhere! Interactive atmosphere takes visitors on a decade-by-decade journey. Immersive exhibits, vintage vehicles, signage, a Valentine diner, and personal stories are all included in this Route 66 must see.
Representing the highway’s golden age this restored 1936 Art Deco gem stands out with its sleek tower, neon signage, and emerald-green-and-cream color scheme. Architecturally stunning with visitor center and café having retro vibes, Route 66 memorabilia, and classic diner fare.
Another top icon of the mother road, 10 classic Cadillacs (1949–1963 models) buried nose-first in a wheat field at a 45-degree angle, covered in layers of vibrant graffiti. One of the most photographed stops on the entire Mother Road—grab some spray paint and go to work. Roadside Americana!
Famous for its glowing neon sign (“It would be a swallow to stay here”), this is a beautifully preserved motor court from 1939. Americana restoration at its finest. One of the top landmark spots for photos (especially at night), and it still operates as a hotel today. Pair this with Tee Pee Curious. This teepee-shaped curio shop has neon and unique architecture
Features an impressive collection of classic cars, hot rods, and Route 66 memorabilia. A top draw for car enthusiasts and history buffs, offering a deeper dive into the automotive culture that defined the Mother Road. Check out Blue Hole as well.
“Route 66 crossing Route 66” intersection at 4th & Central. This is a lively area with diners and restored neon signs speaking to travelers, day and night.
Hit Eagles’ song “Take It Easy,” inspired statue of a man (with a flatbed Ford), mural and guitar photos. One of the most frequently photographed stops of the Mother Road. Easy stop for rockin’ photos and an essential for music lovers. Speaking of hits, the infamous Meteor Crater is only 26 miles away. Both locations rock.
Visitors can stay in concrete teepee-shaped rooms in one of the only Wigwam Motels remaining. This preserved 1940s era court allows itself for photos with vintage cars and neon. The quirky, retro charm is why it is ranked as one of the top overnight stops.
The only national park directly along Route 66, with colorful badlands, ancient, petrified wood, hiking trails, and the historic Painted Desert Inn; blends natural beauty with roadside history.
Referred to as the “Birthplace of Historic Route 66” revival, this small town offers a concentrated stretch of preserved neon, colorful murals, classic cars, quirky shops, Angel & Vilma’s gift shop, and the famous Snow Cap Drive-In. If this are looks familiar it is because it inspired elements of the movie Cars. Food, souvenirs, and nostalgia align this segment.
Great Route 66 Drive-Thru Sheild, nearby murals and a restored powerhouse, and exhibits all tell a tale of the Mother Road and her glory.
A lively old mining ghost town with wild burros roaming the streets, gunfight reenactments, and historic Oatman Hotel; adds Wild West flair.
Its retro architecture and neon vibe make it a standout symbol of Route 66’s heyday of roadside lodging. Another of the few remaining, this motor court, built in the 1940’s, is a hit for lodging or just taking photos among the palm trees and vintage cars.
Interactive exhibits, artifacts, and history in a restored depot; a solid educational stop.
Hundreds of colorful glass bottles welded onto metal “trees” and structures, create a shimmering desert forest along the roadside. This free, large-scale folk art lends itself to one of the most unique and photogenic attractions on the Mother Road.
One of the top icons and “End of the Trail”. The oceanfront view and sign at the pier (near Santa Monica Boulevard/Olympic) combine to promote seaside fun with Route 66 nostalgia. A Ferris wheel, arcade, beach views, and celebratory atmosphere line the strip. Enjoy!
