June 5-6. Vinita Route 66 Festival
Held in the hometown of Cyrus Avery, this centennial festival will include a car show, live music, shopping booths, vendors, a carnival, a truck and tractor show, inflatable park and a kid’s zone in Downtown Vinita.
June 6. 100 Miles Road Rally
Find out why the Midpoint Corridor is known as the “100 Greatest Miles” of Historic Route 66, with cities from Sapulpa to Edmond. The grand prize of $1000 plus many more fun prizes will be awarded at our official party at the Chicken Shack in Arcadia on June 6 at 6 p.m held at Various locations.
100greatestmiles.com/100-miles-road-rally
June 12 Art Crawl on 66: Centennial Edition
On the second Friday of every month, the Historic Red Fork District comes to life with people, local art and music for an open air art market shopping experience! This year’s theme is centered around the Mother Road 100th anniversary.
Historic Red Fork District, 2615 W. 40th Place
June 12. Films on the Lawn: “Cars”
Rev up your engines for a screening of “Cars” at Philbrook, celebrating the birthday of the Mother Road. Ka-chow! at Philbrook Museum of Art, 2727 S. Rockford Road.
June 12 “Cars” at Gathering Place
The classic Pixar film is coming to Gathering Place for a special anniversary screening at the Gathering Place, 2650 S. John Williams Way.
June 18-21 Mid America Route 66 Festival and Cruise
This four-day festival will include a cruise, food trucks, kid’s zone, drag racing event, car show and more at the Claremore Expo, 400 Veterans Parkway, Claremore. visitclaremore.com/events/mid-america-ford-shelby-nationals-5/2026-06-18/
June 20 Route 66 Series: “Two Lane Blacktop”
Circle Cinema invites you to get your flix on Route 66 at a special monthly film series celebrating the centennial throughout 2026! June’s screening is “Two Lane Blacktop” at the Circle Cinema, 10 S. Lewis Ave.
circlecinema.org/movies-events/route-66-june-2026
June 23. “Reflections on Route 66”
Starlight Concert Band will be performing a show titled “Reflections on Route 66,” in which they’ll take attendees on an audio adventure from the Windy City to the City of Angels as they celebrate 100 years of the Mother Road at Guthrie Green, 111 Reconciliation Way.
June 23. Make Your (Land)Mark
Become an engineer and architect as you design and build your own Route 66-inspired landmark. Explore structure, creativity and the spirit of America’s most iconic highway. Please note this activity is for first-fifth graders only at Schusterman-Benson Library, 3333 E. 32nd Place.
June 25-28. Sand Sculpture Showcase
Watch the spirit of Route 66 come alive through a sand sculpting demonstration as a master artist will transform sand into detailed scenes inspired by the iconic Mother Road, celebrating its history and creativity in real time at the Gathering Place, 2650 S. John Williams Way.
June 25-July 18 “Get Your Kicks!” Shoe Art Competition
Celebrate the Route 66 Centennial with a creative twist! Local artists will transform kicks into Route 66–inspired works of art—and you get to vote for your favorites during the three weeks leading up to Gathering Place’s Route 66 Festival at the Gathering Place, 2650 S. John Williams Way.
June 27-28. Route 66 Road Fest
The Route 66 Road Fest, presented by AAA, is a one-of-a-kind celebration giving you the chance to take a journey through the history, attractions, landmarks and fun of the historic highway at the Expo Square, 4145 E. 21st St. Tulsa.