Route 66, America’s historic highway, winds through the heartland states of Missouri, Kansas, and Oklahoma like a ribbon of adventure. This legendary road trip route offers travelers a chance to step back in time and experience quirky roadside attractions, stunning natural wonders, and small-town charm. Whether you’re a history buff, nature lover, or just looking for some good old-fashioned fun, these three states deliver unforgettable stops along the Mother Road.
1. Gateway Arch National Park (St. Louis, Missouri)
Standing proudly at 630 feet tall, this gleaming stainless steel monument marks the starting point for many Route 66 adventures. The Gateway Arch represents America’s westward expansion and offers breathtaking views from its observation deck.
Visitors can take a unique tram ride to the top, where panoramic views of St. Louis and the Mississippi River await. The recently renovated museum beneath the arch tells the fascinating story of American pioneers and explorers who shaped the nation.
For the full experience, combine your arch visit with a riverboat cruise on the mighty Mississippi. The surrounding Jefferson National Expansion Memorial grounds provide perfect picnic spots and photo opportunities of this iconic American landmark.
2. Meramec Caverns (Stanton, Missouri)
Hidden beneath the rolling hills of the Ozarks lies a spectacular underground wonderland that once sheltered Jesse James and his gang of outlaws. Meramec Caverns features seven levels of maze-like passages adorned with colorful formations that took millions of years to create.
The 80-minute guided tour winds through massive rooms with names like the Wine Table and the Theater Room. Marvel at the 70-foot tall Wine Room formation or the shimmering Stage Curtain, a rare onyx formation illuminated by a dazzling light show.
Outside the caverns, families can enjoy boat rides, canoe trips, and a zipline. This roadside attraction has been drawing Route 66 travelers since 1935 with its famous barn advertisements declaring it “America’s Greatest Cave.”
3. Cars on the Route (Galena, Kansas)
Remember Tow Mater from the Pixar movie “Cars”? The inspiration for this beloved character sits right here at this quirky gas station in tiny Galena. The 1951 International boom truck-turned-tow truck became famous worldwide after the movie’s release.
Originally called “4 Women on the Route,” this restored Kan-O-Tex station now serves as a delightful pit stop where travelers can grab a snack, browse Route 66 memorabilia, and snap photos with several character-inspiring vehicles. The friendly staff shares stories about the station’s history and the town’s mining heritage.
Don’t miss the chance to see other vehicles that inspired Pixar characters, including a 1949 Plymouth that resembles Doc Hudson. This charming roadside attraction perfectly captures the spirit of small-town America along the Mother Road.
4. Blue Whale of Catoosa (Catoosa, Oklahoma)
A smiling blue whale lounges in a pond just off Route 66, creating one of the highway’s most photographed and beloved landmarks. Built in the early 1970s by Hugh Davis as an anniversary gift for his wife who collected whale figurines, this whimsical creation quickly became a must-stop attraction.
Children and adults alike can climb through the whale’s interior, slide down its tail, or jump from its diving platforms. Though swimming is no longer permitted, the surrounding picnic area makes it a perfect lunch spot with plenty of shade trees and tables.
The Blue Whale underwent restoration in recent years, preserving its charm for future generations. This quirky roadside attraction perfectly captures the playful spirit of Route 66, where unexpected treasures await around every bend.
5. The Coleman Theatre (Miami, Oklahoma)
Step back into the Roaring Twenties at this magnificently preserved Spanish Colonial Revival theater. Built in 1929 by mining magnate George Coleman, this opulent showplace was designed to bring big-city entertainment to small-town Oklahoma during the early days of Route 66.
The theater’s stunning interior features crystal chandeliers, intricate plasterwork, and a mighty Wurlitzer pipe organ that still fills the space with music. Guided tours reveal fascinating stories about famous performers who graced its stage, from Will Rogers to Judy Garland.
Today, the Coleman hosts movies, live performances, and special events thanks to dedicated community restoration efforts. The theater’s striking façade lights up downtown Miami (pronounced My-AM-uh by locals) at night, beckoning travelers to experience a touch of vintage glamour along the historic highway.
6. Ed Galloway’s Totem Pole Park (Foyil, Oklahoma)
Rising 90 feet into the Oklahoma sky stands the world’s largest concrete totem pole, a testament to one man’s creative vision and dedication. Ed Galloway, a retired manual arts teacher, spent nearly two decades crafting this remarkable folk art environment as his personal tribute to Native American culture.
The main totem pole features hundreds of intricate carvings of birds, animals, and indigenous symbols, all hand-painted in vibrant colors. Surrounding it are smaller totems, concrete picnic tables shaped like mushrooms, and a unique fiddle-shaped building housing Galloway’s handmade violins.
Wander the grounds at your own pace to appreciate the incredible detail in each carving. This hidden gem represents the kind of unexpected roadside wonder that makes Route 66 so special – where passionate individuals turned their visions into landmarks that continue to amaze travelers today.
7. Gary’s Gay Parita (Ash Grove, Missouri)
Travel back to the heyday of Route 66 at this lovingly recreated 1930s Sinclair gas station. Though the original station burned down decades ago, Gary Turner rebuilt it as a labor of love, collecting vintage gas pumps, signs, and memorabilia to create an authentic slice of roadside Americana.
While Gary passed away in 2015, his daughter Barbara continues his legacy of hospitality. Visitors receive the same warm welcome that made Gary famous among Route 66 enthusiasts worldwide – complete with stories, cold sodas, and genuine conversation.
The station doesn’t actually sell gas anymore, but it offers something far more valuable: a chance to experience the friendly spirit of travel in simpler times. Don’t rush your visit; this is a place to slow down, sign the guest book, and savor a genuine connection to Route 66’s golden age.
8. Pops Soda Ranch (Arcadia, Oklahoma)
You can’t miss the giant 66-foot tall soda bottle sculpture that glows with ever-changing LED lights after dark. This modern Route 66 landmark houses a gas station, restaurant, and a mind-boggling selection of over 700 different flavors of soda pop arranged in rainbow-colored rows.
From classics like root beer to bizarre concoctions like buffalo wing soda and bacon soda, the selection delights both kids and adults. The round building’s glass walls create a kaleidoscope effect as sunlight streams through the colorful bottles, making for spectacular photo opportunities.
The attached diner serves up classic American road food with a modern twist. Grab a burger and a flight of unusual sodas to sample on the patio while watching the sunset illuminate the giant bottle. Pops proves that new attractions can capture the playful spirit of historic Route 66.
9. Route 66 Drive-In Theatre (Carthage, Missouri)
Experience the golden age of American entertainment at one of the few remaining drive-in theaters along Route 66. Originally opened in 1949 as the 66 Drive-In, this nostalgic attraction closed in the 1980s but was lovingly restored and reopened in 1998, preserving a cherished piece of roadside history.
Pull your car up to one of the speaker posts, tune your radio to the right frequency, and enjoy current double features under the stars. The original neon-lit sign and projection building transport visitors back to simpler times when families gathered in station wagons for affordable entertainment.
The snack bar serves up classic movie treats like buttery popcorn and hot dogs. For the full experience, arrive early to secure a good spot and watch the sunset before the show begins – a perfect way to experience authentic Americana along the Mother Road.
10. Will Rogers Memorial Museum (Claremore, Oklahoma)
“I never met a man I didn’t like” – these famous words from America’s beloved humorist and Oklahoma native Will Rogers capture the spirit of this fascinating memorial. Set on a hilltop overlooking the rolling countryside, this limestone museum houses the world’s largest collection of Rogers memorabilia.
Exhibits trace his remarkable journey from Cherokee cowboy to international star of vaudeville, movies, radio, and newspapers. Don’t miss the theater showing Rogers’ films and the saddle collection highlighting his famous rope tricks. The beautiful grounds include Rogers’ tomb, facing west toward the setting sun.
Even visitors unfamiliar with Rogers leave with appreciation for his homespun wisdom and humor that captivated America during the early days of Route 66. His social commentary remains surprisingly relevant today, making this stop both entertaining and thought-provoking for modern travelers.
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