8 Cute Small Town Drives In Oklahoma

Oklahoma turns a simple drive into something memorable, with stretches of Route 66 linking quirky roadside landmarks, classic diners, and small towns full of character. A road that starts as a quick trip out of Tulsa or Oklahoma City can turn into a walk across an old steel-truss bridge, or lunch under the glow of a towering soda bottle. Route 66 ties many of those moments together, especially in the state’s smaller towns, where old murals, museums, and roadside landmarks still give the road much of its character. Here’s a look at eight cute small towns and eight relatively short drives in Oklahoma, all of them connected in one way or another to Route Six-Six.

Arcadia: The Round Barn, Pop’s 66 Soda Ranch

You’re on this trip to experience the lighter, more playful side of Route 66. 89 miles (about a 90-minute drive) from Tulsa, or 22 miles (a 26-minute drive) from OKC, you’ll find Arcadia, a town with some of Route 66’s most playful roadside appeal. Take The Round Barn, for instance. Oklahoma’s only wooden round barn predates Route 66, having been built in 1898. It nearly stopped being an attraction, or even existing at all, when its roof collapsed in 1988. Enter Luke Robison, a retired contractor, who enlisted a group of fellow-minded and fellow-aged contractors (known collectively as The Over-The-Hill Gang, as most all over 65 at the time) to restore the roof, and reopened it in 1992. Inside, you’ll find exhibits, a gift shop, and the Arcadia Historical and Preservation Society. Taken together, it makes for a memorable stop.

If you’re ready for a break, Arcadia is also home to Pop’s 66 Soda Ranch, as well as an old-fashioned diner serving chicken-fried steak, burgers, and hand-made milkshakes and malts. To find Pop’s, look for the 66-foot-tall soda bottle covered in LED lights right on the side of 66.

Claremore: The Will Rogers Memorial Museum, and the Surrey With The Fringe On Top

27 miles (about half an hour) from Tulsa, or about 140 miles from Oklahoma City (roughly two hours away), is the town of Claremore. You’ve probably heard the phrase “I never met a man I didn’t like”. That’s a quote from a man who, prior to his untimely death in a 1935 plane crash, was one of the biggest celebrities in America, a man named Will Rogers. He appeared in the Ziegfeld Follies alongside Fanny Brice and W.C. Fields. He had a radio show. He had a syndicated newspaper column. He appeared in movies. And he hailed from a ranch near Oologah. The Will Rogers Memorial Museum includes saddles and lassos that belonged to Rogers (who, in addition to everything mentioned above, was an actual cowboy), shows films he appeared in, and has the personal items he had with him at the time of the airplane crash.

Also in Claremore is an exhibit to a slightly more obscure figure, one Lynn Riggs. He was a playwright; his play Green Grow The Lilacs isn’t a household name, but the musical it inspired, Oklahoma!, certainly is. And yes, the Lynn Riggs exhibit includes a Surrey With The Fringe On Top. Human tourists are encouraged; ducks and geese and chicks, however, better scurry.

Sapulpa: Waite Phillips Filling Station, and Pretty Water

The town of Sapulpa is 18 minutes (15 miles) from Tulsa, and 93 miles (90 minutes) from Oklahoma City. In Sapulpa, there is an old gas station built in the 1920s by Waite Phillips, and it houses a collection of historic and visually distinctive roadside pieces. The filling station is a museum for cars built in the 1920s, the kind that might well have rolled down 66 in its heyday. Of course, you may want to veer away from things automotive for a moment; if so, Sapulpa can accommodate you. There is a lake in Sapulpa whose actual, literal name is Pretty Water Lake. Pretty Water Lake offers trout fishing, a hiking trail, and other natural opportunities to decompress from the road.

Chandler: What’s Route 66 all about, anyway?

Chandler, Oklahoma, is essentially at the midpoint between Tulsa and Oklahoma City; 65 miles from the former, 45 miles from the latter. Chandler boasts the Route 66 Interpretive Center, which offers an interactive, immersive trip down the legendary road from its rise in the 1920s to its last hurrah in the 1960s, with vintage billboards and virtual hotel rooms along the way. It’s a solid journey down 66, and what it has been, and what it has meant. For a less “official” but by no means less sincere interpretation of 66, there’s McJerry’s Route 66 Gallery, also in Chandler. The brainchild of Jerry McClanahan, a Chandler-based artist and author, the museum offers his work; prints, paintings, postcards, and even coloring books designed by Jerry are on offer here, all devoted to one subject. Hint: it’s 2,488 miles long.

Clinton: The Route 66 Museum and The World’s Largest Curio Cabinet

Clinton, Oklahoma, is 192 miles (nearly 3 hours) from Tulsa, and 84 miles (80 minutes) from Oklahoma City. After either drive, you’ll have seen a lot of Route 66, and may find yourself ruminating again about what 66 means, or has meant, or maybe you’re just a history buff with a fondness for this road. Also, it’s probably time to get some souvenirs for the folks back home. In Clinton, the Oklahoma Historical Society operates the state’s official Route 66 Museum; like the Interpretive Center in Chandler, it offers exhibits about the construction of 66, traveling down it, and the myriad of restaurants, garages, and roadside curiosities along the way. Here in Clinton, however, the rooms are musically themed, and songs inspired by the road play in each room, like Woody Guthrie’s “Will Rogers Highway”, for example. There’s also the matter of souvenirs, of course, and the museum has a gift shop, and the exhibits begin with ‘The World’s Largest Curio Cabinet. It’s a great idea, a fun, nostalgic throwback to the kind of roadside attractions that were all the rage in Route 66’s heyday, the kind of thing “Weird Al” Yankovic sang about in his “Biggest Ball of Twine In Minnesota”.

Elk City: The National Route 66 Museum Complex and Ackley Park

Elk City, 219 miles (three hours, fifteen minutes) from Tulsa and 111 miles (101 minutes) from Oklahoma City, offers one more Route 66 museum, or rather a whole complex of them. It’s a national museum, so it extends beyond Oklahoma, covering all eight states through which The Mother Road runs. You can even drive the whole Route, in a manner of speaking, in a 1955 Cadillac (pink, of course). If you’re tired of the Route itself, the complex also includes museums devoted to pioneer life and rodeo life, and a replica of an old-fashioned general store. You can find the complex by looking for Myrtle, a nearly two-story kachina doll at the entrance. Or, if you’ve seen enough about Route 66 itself, there’s Ackley Park, especially recommended if your kids or grandkids are with you. Right next to the museum complex, Ackley boasts stocked fishing ponds, playgrounds, mini golf, a train ride, and a wooden carousel with 36 hand-carved horses and two chariots. The carousel adds another playful stop for families visiting the museum complex.

Chelsea: The Pryor Creek Bridge, The Pedestrian Underpass Mural

46 miles from Tulsa (about 51 minutes driving) and 158 miles from OKC (a two-and-a-half-hour drive) is the town of Chelsea. After either drive, you’ll likely be ready to stretch your legs; Chelsea offers you two opportunities along 66 to do just that, with a pair of memorable roadside stops.

There are whole sections of road and street that are former sections of 66, no longer serving as part of the highway; one of them, the Pryor Creek Bridge, is in Chelsea. It’s a 123-foot-long steel-truss bridge that isn’t open to auto traffic anymore; it is open to foot traffic and invites plenty of photo opportunities. Also accessible on foot is the Pedestrian Underpass Mural at Walnut and West Sixth Street. It’s the result of the city cleaning and renovating the overpass in 2016, and commissioning Kenneth Hollingshead to paint a mural depicting the parts of 66 that run through Chelsea. There are probably many opportunities to walk alongside 66 in Oklahoma and elsewhere; this is a rare chance to briefly walk under it.

Catoosa: The Blue Whale

Catoosa is 15 miles (about 20 minutes) from Tulsa and roughly 120 miles (about two hours) from Oklahoma City. Its signature Route 66 attraction is the Blue Whale of Catoosa, one of Oklahoma’s best-known roadside landmarks. Built by Hugh S. Davis, the whale began as a hand-drawn idea and became an 80-foot-long, 20-foot-tall structure made from steel and concrete. The site is temporarily closed for renovations, but travelers can still stop in Catoosa for a quick Route 66 photo detour and visit the D.W. Correll Museum, where Blue Whale souvenirs are being sold.

Why These Route 66 Drives Stay With You

“Cute” is a funny word. It’s one of the most subjective words in our language. It can mean “funny”, it can mean “young”, it can mean “old”. Cute may be hard to define, but these towns make a strong case for it. These brief jaunts along Route 66, all within Oklahoma, offer plenty of Americana and a memorable look at the state’s small-town roadside culture.