Oklahoma's 'Winery And Grape Capital' Is A Humble Quirky Gem Hidden Along Historic Route 66

Stretching from Chicago all the way to the Santa Monica Pier, Route 66 is one of the most stunning and storied routes for a U.S. road trip. Passing through eight states and covering over 2,400 miles, the iconic route is packed with underrated hidden gem stops, from oversized roadside attractions like the kitschy Muffler Men to frozen-in-time towns lined with retro motels and neon signs.

Boasting more drivable portions of the historic route than any other state, Oklahoma is home to some of the best Route 66 attractions. Tucked into a tapestry of picturesque pastures adorned with windmills and serene stretches of two-lane highway, sleepy Oklahoma towns on Route 66 like Chelsea are the most charming. Situated about halfway between Tulsa and Oklahoma City, Stroud is one such town. Not only is it brimming with history and Route 66 landmarks, but it's also named the state's "Winery and Grape Capital" by the Greater Oklahoma City Chamber, offering plenty of places to stop and sip. Whether you're tackling the route in its entirety or just exploring the Oklahoma portion, Stroud is a must-stop destination on Route 66.

It's difficult to talk about a Route 66 town without highlighting its quirky roadside attractions. In Stroud, the most famous is the Rock Café, a beloved diner dating back to 1939. Its most unique characteristic is its architecture. Inspiring its name, the Giraffe-style exterior is built from locally quarried sandstone recovered from the original paving of Route 66. Erected in the 1940s, a retro neon sign stands tall. Listed on the National Register of Historic Places, the local haunt is also an officially designated Route 66 landmark, marked by a small sign outside. You may also recognize the car-shaped cutouts parked out front from the animated film "Cars." Filmmaker John Lasseter and the Pixar crew visited Stroud while researching for the Route 66-inspired flick, and the character Sally Carrella is a caricature of café owner Dawn Welch. Inside the café, you'll find memorabilia signed by the filmmakers — including a "Cars" movie poster — along with other Route 66 signage and a painted two-lane highway stretching across the floor.

Once you've had your fill of classic diner fare, visit the Route 66 Spirit of America Museum, which celebrates Americana through a variety of unique pop culture exhibits. Explore a life-size recreation of Clark Kent's office from "The Adventures of Superman," get lost in a room dedicated to space exploration and space-centric media, and catch a film screening in the Wonder Woman Theater. Open Wednesday through Saturday from 10 a.m. to 6 p.m. and Sundays from 1 p.m. to 6 p.m., the spirited museum is a must-visit for history buffs and pop culture nerds. If you're staying the night in Stroud, be sure to check into the Skyliner Motel, a retro roadside retreat ornamented with a vintage neon sign.

In addition to its Route 66 charms, Stroud is a vibrant wine destination. Sip vino crafted from locally grown grapes at Stable Ridge Winery. Operating since 2000, the family-owned winery is open for tastings five days a week, offering a variety of red, white, and blush wines, including fruit-forward flavors like strawberry Moscato. Before you head out, peruse their boutique gift shop for vino-centric accessories, stemless glasses, and locally bottled wine.

For a rural retreat, make the short trek to Sparks Vineyard & Winery, about 15 miles southwest of the heart of Stroud. Situated at the end of a quiet dirt road, the hidden gem hosts wine tastings on most weekends from 11 a.m. to 5 p.m. (call to confirm they're open), sampling sweet, fruity, and dry wines in a peaceful atmosphere. If you're visiting during summer, be sure to plan around the Stroud Summer Festival. Sip regional wines paired with delicious foods from local vendors, browse vibrant arts and craft booths, catch live music performances, and enjoy a classic car show in the heart of downtown on Route 66. For non-alcoholic ventures near Stroud, continue about 40 miles on Route 66 to POPS 66 Soda Ranch, Oklahoma's iconic roadside gem serving over 700 sodas and tasty sweet treats.