Location: Bloomington-Normal, IL
When: Typically held in June
This annual festival is a must-see for Route 66 fans. Celebrating the history and culture of the Mother Road, it features classic car shows, live music, local vendors, parades, and more. It’s a family-friendly event where you can immerse yourself in the nostalgia of the iconic highway while enjoying the lively atmosphere.

Location: Springfield, IL
When: Held in September
Springfield’s Route 66 Mother Road Festival is a fantastic event for festival-goers who love classic cars. The festival features a huge car show with vehicles from the 1920s to the 1970s, showcasing restored classics and rare finds. There are also live bands, food trucks, and fun activities for all ages, making it a vibrant stop for Route 66 road trippers.

Location: Shawnee National Forest (Carbondale), IL
When: June
This family-friendly festival celebrates the local history of the Shawnee area with a parade, a carnival, food stands, and music performances. It’s a fun way to experience local culture while enjoying the lively atmosphere of a small-town festival with a touch of Route 66 charm.

Location: Springfield, IL
When: August
If your route takes you near Springfield, be sure to check out the Illinois State Fair, one of the largest and most popular festivals in the state. While not strictly a Route 66 event, this fair celebrates Illinois’ agricultural heritage with rides, live entertainment, food competitions, and more. It’s a great stop to take a break from the road and enjoy a mix of fun activities.

Location: Chatham, IL (near Springfield)
When: September
For a more local flavor, the Chatham Apple Festival is a fantastic way to enjoy a quaint, small-town festival. The event features apple-related treats, arts and crafts, local music performances, and a parade. It’s a relaxed atmosphere where you can enjoy the seasonal charm of Illinois as you travel through Route 66.

Location: Joliet, IL
When: June
The Taste of Joliet is a food festival that celebrates local cuisine, and it’s a perfect stop for food lovers driving along Route 66. Enjoy everything from local dishes to international flavors, plus live music performances. It’s a great chance to experience the food culture of Illinois while mingling with the locals.

Location: Various towns along Route 66
When: Varies, typically in September
This festival brings together communities from towns along Illinois Route 66 to celebrate the iconic highway with parades, vintage car shows, arts and crafts, local performances, and more. Each town along the route has its own way of celebrating, offering festival-goers a unique experience in every stop.

Location: Peoria, IL
When: June
If you’re passing through Peoria, don’t miss the Peoria Riverfront Festival. This event celebrates the arts, music, and culture of the region, with performances by local bands, art vendors, food stands, and more. It’s a lively and diverse festival that offers a little bit of everything, set along the scenic Illinois River.

Location: Carlinville, IL (Near Route 66)
When: September
If you’re passing through the fall months, check out Carlinville’s Pumpkin Festival. This small-town festival celebrates the harvest season with pumpkin-themed events, contests, parades, and carnival rides. It’s a charming stop to enjoy the autumn atmosphere while continuing your Route 66 journey.

Location: Springfield, IL
When: June
For motorcycle enthusiasts traveling Route 66, the National Route 66 Motorcycle Rally in Springfield is an exciting event to add to your itinerary. With bike shows, scenic rides, and local food vendors, this festival celebrates the motorcycle culture that has long been a part of Route 66’s history.

Location: Chicago, IL
When: June
For music lovers, the Chicago Blues Festival is one of the largest free blues festivals in the world. Held in Grant Park in Chicago, it celebrates the rich history of blues music, which played a significant role in shaping the culture of Route 66. While you might not be directly on Route 66 in Chicago, it’s the perfect event to enjoy a weekend of live performances, local food, and vibrant culture.

Location: Champaign, IL (Near Route 66)
When: August
If you’re a foodie and enjoy a fun outdoor festival experience, the Great American Bison BBQ Festival is an exciting event in Champaign, offering BBQ competitions, craft beer tastings, and live music. It’s a great way to sample some of Illinois’ best flavors and enjoy the lively atmosphere.

Location: Pontiac, IL
When: June
Another wonderful festival on Route 66 is the Route 66 Blues & BBQ Festival in Pontiac, Illinois. This event combines two great loves of the area—blues music and barbecue. Enjoy live blues performances, delicious food, and family-friendly activities. It’s a laid-back and fun way to immerse yourself in local culture while traveling through the historic towns of Illinois.

Location: Granite City, IL (Near Route 66)
When: February
If you’re traveling Route 66 in the winter, the Mardi Gras Festival in Granite City is an exciting event to experience. Featuring a parade, live bands, and authentic New Orleans food, it brings a bit of the Big Easy to Illinois, making it a fun pit stop for festival-goers.

Location: Cuba, MO (Just off Route 66)
When: September
While just outside Illinois, this celebration is a short detour and one of the largest Route 66 events in the country. Featuring live music, classic cars, and a parade, this festival is a true celebration of the Mother Road’s legacy.

Check Local Schedules: Illinois has a number of unique, region-specific festivals, so be sure to check dates and local event calendars when planning your trip.
Pack for Weather: Festivals can take place in any weather conditions, so pack appropriately for both hot summer days and cooler evenings.
Plan for Crowds: Many of these festivals are popular, so make sure to plan your accommodations early if you’re attending larger events like the Route 66 Festival or Illinois State Fair.

Wandering Souls