When: August
Why: This festival is a great celebration of the iconic Route 66 and is a must-attend for festival-goers traveling the Mother Road. The Coffeyville Route 66 Festival features live music, food trucks, vintage car shows, and family-friendly events. It’s a fantastic place to immerse yourself in the history and spirit of Route 66 with a fun, local vibe.

When: September
Why: If you're in Kansas during September, the Kansas State Fair in Hutchinson is a can't-miss event. While it’s not strictly Route 66, it’s a major celebration of Kansas culture with agricultural displays, carnival rides, live performances, rodeo events, and an extensive food court. It's a great place to dive into Kansas' rural life and vibrant community atmosphere.

When: August
Why: This annual festival celebrates the history, culture, and charm of the Pittsburg area. It features local artisans, live music, a car show, and activities for the whole family. Enjoy the small-town charm of Route 66 while taking in the best of Kansas' artistic and cultural scene. You can explore the streets, enjoy local food, and participate in fun activities like face painting and games.

When: June
Why: For music lovers, the Baldwin City Bluegrass Festival offers an authentic and fun experience. Held in Baldwin City, a bit off Route 66, this event features traditional bluegrass bands, great food, and plenty of opportunities to enjoy Kansas’ musical heritage. This festival brings in top-notch performances and offers a friendly, lively atmosphere.

When: September
Why: Winfield’s Fiddlers’ Festival celebrates one of Kansas' most beloved music genres: bluegrass and fiddling. The festival features a series of competitions, live performances, and jam sessions. It’s a great opportunity to soak in the folk music culture of Kansas and experience a truly homegrown musical tradition. You’ll find plenty of lively crowds and talented performers.

When: October
Why: If you’re a film lover, the Kansas International Film Festival is a must-attend event in the fall. Held in Overland Park (just off Route 66), this festival celebrates independent filmmakers from all over the world. You can watch film screenings, participate in panel discussions, and explore the best of independent cinema. The festival also provides an opportunity to connect with local artists and filmmakers.

When: May
Why: For nature and history lovers, the Tallgrass Prairie Festival offers a unique celebration of Kansas’ natural beauty. Held in Matfield Green, near the Tallgrass Prairie National Preserve, the festival features educational talks, guided hikes, nature walks, and art displays, all while celebrating the native tallgrass prairie ecosystem. It’s a fun and educational event that connects you to the natural and historical roots of Kansas.

When: September
Why: This famous festival in Winfield draws visitors from all over the country to enjoy a weekend of acoustic music. The Walnut Valley Festival features folk, bluegrass, and country music, with tons of performances, workshops, and jam sessions. With its focus on acoustic music, this is a perfect festival for those who love intimate, live performances and the spirit of Kansas’ musical culture.

When: Seasonal (Summer)
Why: For baseball enthusiasts, catch a Kansas City Royals game at Kauffman Stadium during your Route 66 trip. While not a festival per se, attending a Royals game is a quintessential Kansas experience. The stadium is known for its relaxed vibe and great food, making it a fun outing for festival-goers looking to mix sports with local culture.

When: Labor Day Weekend
Why: Kansas City’s Irish Fest is one of the largest Irish festivals in the Midwest, and it’s a fantastic cultural event to attend if you’re traveling through Kansas. The festival includes live Irish music, dance performances, cultural exhibits, and delicious Irish food and drinks. It’s a great way to explore Irish heritage and enjoy lively festival activities.

When: Summer months (specific dates vary)
Why: For vintage car enthusiasts, various towns along Route 66 in Kansas host car shows and cruising events. These events typically feature classic cars, trucks, and motorcycles, along with live music, food vendors, and family-friendly activities. It’s a great way to immerse yourself in Route 66 culture and meet other travelers who share your passion for classic cars.

When: June
Why: Old Shawnee Days is a fun-filled festival that celebrates Shawnee’s local history with parades, carnival rides, food stalls, and live entertainment. The festival draws in locals and tourists alike for a weekend of family-friendly activities. It’s a great event to attend for those looking to experience Kansas’ small-town charm with some good ol' fashioned fun.

When: July
Why: The Kansas Wheat Festival celebrates the state’s agricultural roots, particularly its wheat-growing legacy. With a parade, a carnival, and various contests, this festival allows you to experience the essence of rural Kansas while enjoying activities like baking contests, wagon rides, and live entertainment.

When: April
Why: This annual arts festival in Wichita is one of the region’s largest celebrations of creativity. It features hundreds of local artists, performances, art exhibits, and live music. If you’re traveling along Route 66 in Kansas during spring, the Festival of the Arts offers a great way to experience the city’s vibrant art scene and engage with local creators.

Check Local Event Schedules: Many Route 66 festivals in Kansas are seasonal, so make sure to check the local event calendars for up-to-date information on festival dates.
Look for Smaller, Local Festivals: Kansas has many small-town festivals that celebrate local culture, food, and traditions. Be sure to ask locals about upcoming festivals as you drive through each town.
Plan for Kansas Weather: Depending on the season, Kansas can be quite hot in the summer and chilly in the winter. Be sure to dress appropriately for outdoor festivals, especially in the warmer months.

Wandering Souls