Weekly Events Calendar: May 18-24, 2026

Weekly Events Calendar: May 18-24, 2026

By Miguel Rios

Each week, Oklahoma Today staffers comb through their calendars to find a handful of great events happening across the state. Get out! See Oklahoma! And be sure to let us know what you find, either here or on Facebook, Twitter, and Instagram at @oklahomatoday.

Claremore’s Boots on the Boulevard is a rodeo fan’s dream. Not only does it help kick off the Will Rogers Stampede PRCA Rodeo, but it’s a free rodeo-themed festival for the whole family. Downtown Claremore shuts down for an evening of shopping, eating, and enjoying live music. It’s probably the best way to start a rodeo weekend, and if you prefer sneakers, you don’t even have to wear boots!
May 21. Admission, free. visitclaremore.com

Some traditions just don’t go out of style—and for good reason. Old Tymers Day invites you to step back in time and participate in a century-long celebration in Oilton. The event promises to evoke fond memories and nostalgia for days past with activities like the balloon toss and turtle race. Participants can also join a 5K race, savor a pancake breakfast, enjoy a historical parade, and even watch the Oilton pageant. Old Tymer’s Day is truly one for the ages.
May 23. Admission, free.
oiltonchamber.org

Bicyclers and revelers of all kinds will take part in the parade at Oilton's Old Tymers Day. Balloon tosses, turtle races, pancake breakfasts and more will highlight the day of fun May 23. Photo courtesy Oilton Chamber of Commerce

In case you haven’t heard, Route 66 is celebrating its centennial anniversary this year. You can expect to see events to celebrate the Mother Road’s milestone all year long, like Bethany 66 Festival. This annual festival is one big, family-friendly block party with something for everyone—a car show, tons of live music, children’s activities, local vendors showcasing arts and crafts, and of course, food trucks. That has to be one of the best ways to celebrate a hundred years of Route 66. At least until the next centennial event.
May 23. Admission, free.
bethanyimprovementfoundation.com

The Summer of 66 is upon us—celebrate the Route 66 centennial at the Bethany 66 Festival, featuring a car show, live music, vendor booths, and more. Photo courtesy Bethany Improvement Foundation

Gear up for the thirty-sixth annual Tour de Meers bike ride. One of the longest-standing biking events in the region, Tour de Meers started as a small, local event and now sees riders from all over Oklahoma and surrounding states. Cyclists can tackle one of the various bike routes ranging from ten miles to sixty miles on various terrains. If you’d rather give your calves the day off and cheer from the sidelines, you’ll still get to enjoy some of our state’s most scenic views.
May 23. Registration starts at $35.
tourdemeers.org

Art lovers, rejoice! The beloved annual Paseo Arts Festival in OKC is back showcasing the works of over eighty artists from across the country. This Memorial Day weekend tradition transforms the iconic Paseo Arts District into a sprawling outdoor festival complete with a “food court” and twenty food and drink vendors. Grab a bite to eat while you browse the art and enjoy live music from more than fifty live performers. Don’t forget, all the art galleries, specialty shops and restaurants that call the Paseo home will also be open!
May 23-25. Admission, free.
thepaseo.org

A Memorial Day weekend tradition in Oklahoma City, the Paseo Arts Festival returns with plenty of amazing eats, sensational artist booths, and fun activities. Photo by Lori Duckworth

Written By

Miguel Rios