When: Typically held in June
The Route 66 Festival in Tulsa is a must for any Route 66 enthusiast and festival lover. This vibrant celebration brings together classic cars, live music, and Route 66 history. It includes a classic car show, arts and crafts vendors, food trucks, and street performances. It's the perfect way to immerse yourself in the Route 66 culture while enjoying a lively, community-driven festival.

When: Held every September
While not exclusively Route 66-themed, the Oklahoma State Fair is one of the largest and most celebrated festivals in the state. Featuring carnival rides, rodeo events, agricultural displays, live music, and delicious fair food, this event is a great stop for festival goers. The fair's rich history and wide range of entertainment options make it an essential part of the Oklahoma experience.

When: May
The Route 66 Blues Festival in Tulsa is an incredible event for music lovers, especially those who enjoy blues and Americana. Held at various venues around Tulsa, this festival brings together local and national blues artists, offering live performances and jam sessions. It’s an ideal way to enjoy the rich musical heritage of the Route 66 region, with plenty of opportunities to dance, eat, and celebrate.

When: May
Mayfest is a four-day event in downtown Tulsa that celebrates the arts, music, and local culture. It features hundreds of artists and craftspeople, live performances by local and national bands, and a wide variety of food options. For festival lovers, it’s a great way to enjoy the vibrant Tulsa scene while getting a taste of local life along Route 66.

When: First weekend in September
If you’re traveling through the eastern part of Oklahoma on Route 66, the Cherokee National Holiday in Tahlequah is a must-visit. This festival celebrates Cherokee heritage and culture, offering traditional music, dance, parades, arts and crafts, and a powwow. It’s a wonderful cultural experience for those looking to dive deeper into the history and traditions of the Native American tribes of Oklahoma.

When: November
For those who enjoy a mix of fitness and festivals, the Oklahoma Route 66 Marathon in Tulsa is a fantastic way to celebrate both the spirit of Route 66 and your love of running. The marathon is a scenic route through Tulsa, and participants can also enjoy the Route 66 Expo featuring local vendors, live music, and celebrations along the route.

When: July
If you’re a music festival lover, the Woody Guthrie Folk Festival in Okemah is a unique celebration of the legendary folk singer, who was born in Oklahoma. This festival features live music performances by folk artists, workshops, and events that honor Guthrie’s influence on American folk music. It’s an unmissable stop for those traveling along the Route 66 corridor who enjoy folk and Americana.

When: June
For those interested in Native American arts and culture, the Red Earth Festival in Oklahoma City is a major cultural event. It’s one of the largest Native American cultural festivals in the world, featuring traditional dance, art, and crafts from over 100 Native American tribes. This is a great event for festival goers interested in experiencing the region’s indigenous history and traditions.

When: May
Tulsa's Mayfest is one of the biggest cultural events in the city, featuring a mix of art, food, and live music. You’ll find street performers, food vendors, local artists, and live performances from local bands. It’s a wonderful blend of art, music, and community, and a must for any festival-goer traveling through the heart of Route 66 in Oklahoma.

When: October
If you're a fan of music, the Oklahoma Music Hall of Fame Induction Ceremony is a special event celebrating the state's musical heritage. The ceremony is held in Muskogee and features performances, live music, and tributes to Oklahoma's most influential musicians. It’s a great way to enjoy the region’s rich musical legacy while also being part of a special festival event.

When: June
The Bricktown Water Taxi & Music Festival takes place in Oklahoma City’s lively Bricktown district. It features live music performances from local and national artists, boat rides along the river, and fun activities in the historic district. It's a family-friendly festival with a laid-back atmosphere, perfect for those who want to enjoy live music, food, and drink while soaking up the city’s energy.

When: April
Festival of the Arts in Oklahoma City is a springtime event that brings together art lovers, foodies, and performers in the heart of the city. It features visual art displays, live performances, and a wide range of food vendors. It’s an excellent choice for festival goers looking for a blend of culture, food, and entertainment in a beautiful outdoor setting.

When: Throughout the year
For those interested in Western culture, the National Cowboy & Western Heritage Museum in Oklahoma City regularly hosts events that celebrate cowboy culture, including rodeos, music festivals, and Western-themed exhibitions. Check their calendar to see if any events coincide with your trip along Route 66.

When: Fall (dates vary)
Tulsa International Film Festival is perfect for festival-goers who love movies. It showcases a variety of independent films from around the world, often highlighting works from emerging filmmakers. It’s a great way to enjoy a cultural experience while traveling through Tulsa, a city rich in arts and culture.

When: April
Art on the Square in Guthrie, Oklahoma, is a wonderful event for lovers of fine arts and crafts. This annual festival features over 100 artists, along with live music and food vendors. It’s a perfect opportunity to enjoy the beauty of the arts while traveling through one of Oklahoma’s historic towns along Route 66.

Check Festival Dates: Many of these festivals are annual events, so make sure to check the specific dates for your trip. It’s best to plan your journey around these events to make the most of the festival atmosphere.
Local Festivals: Beyond the larger events, Oklahoma has many smaller local festivals and fairs along Route 66. Stop in at small towns for farmer’s markets, craft fairs, and local celebrations.
Stay Flexible: Route 66 offers many spontaneous roadside attractions and events. Be sure to check local calendars or visit tourism offices along the way for impromptu festivals or events you may not have known about.

Wandering Souls