When: Typically held in June.
What to Expect: Springfield, Missouri, hosts one of the most exciting Route 66 festivals in the country. The festival includes a parade, classic car shows, live music, local vendors, and historic tours of Springfield. The event celebrates everything Route 66, with a special focus on the cars and culture that made the highway famous. For any festival-goer, it's a chance to immerse yourself in the history and the road-trip spirit of the iconic route.

When: Late summer or early fall.
What to Expect: Held in the heart of Springfield, this festival marks the "birthplace" of Route 66, where the highway was first recognized in 1926. The festival offers everything from historic reenactments to live music, food trucks, and a celebration of Springfield's contribution to Route 66’s legacy. The event is fun for all ages, with plenty of opportunities to explore the heritage and vibrant community surrounding this iconic route.

When: Early summer.
What to Expect: Cuba, Missouri, known for its Route 66 charm and vibrant murals, hosts a fantastic Bluegrass Festival that celebrates the genre with multiple performances, live music, and local food vendors. It’s an opportunity to enjoy the traditional sound of bluegrass music in a relaxed, family-friendly atmosphere, all while soaking in the Route 66 vibe.

When: August.
What to Expect: While not directly on Route 66, the Missouri State Fair is located just off the highway and is worth a visit for festival lovers. It’s a classic state fair with all the rides, games, and food you could want. There are also livestock shows, live entertainment, and various competitions, making it a great place to experience the best of Missouri’s culture and traditions.

When: Memorial Day Weekend.
What to Expect: If you’re a foodie who loves festivals, St. Louis Ribfest is a must. Celebrate the best barbecue in the region while enjoying live music, local vendors, and cooking demonstrations. As part of your Route 66 adventure, this festival is a great stop to indulge in some of Missouri’s finest food and enjoy the lively atmosphere.

When: June.
What to Expect: While it’s not right on Route 66, this festival takes place in Louisiana, Missouri, along the Mississippi River and is easily accessible from the highway. The festival celebrates the history of the Great River Road and features local arts and crafts, live performances, food, and river-related activities. It’s a fun and festive way to connect with Missouri’s natural beauty and cultural heritage.

When: September.
What to Expect: A celebration of Carthage’s local heritage, Old Settlers Day includes a parade, live entertainment, a carnival, and various community events. It's a great family-friendly festival for anyone traveling along Route 66 who wants to enjoy small-town charm and immerse themselves in local Missouri culture.

When: May.
What to Expect: Located near the outskirts of St. Louis, The Wildwood Flower Festival is a celebration of the arts, with local music, craft vendors, and family-friendly activities. It’s a great stop if you enjoy a relaxed festival atmosphere and a chance to explore local artists and crafters.

When: Typically in May.
What to Expect: If you love classic cars, the Route 66 Car Show in St. Louis is one of the best in the country. The event showcases vintage and modern cars, and festival-goers can admire and photograph the stunning vehicles while enjoying food, entertainment, and local vendors. It’s a perfect blend of history, nostalgia, and automotive passion.

When: September/October.
What to Expect: For festival-goers with a taste for German culture, Oktoberfest in St. Louis is a lively celebration with traditional food, music, and dancing. While not directly tied to Route 66, it’s a fun and festive stop if you’re in the St. Louis area. Enjoy authentic bratwurst, pretzels, and a wide variety of local craft beers in a vibrant atmosphere.

When: Throughout the year.
What to Expect: St. Louis is home to many art and music festivals throughout the year, such as the St. Louis Art Fair (in Clayton) and St. Louis Music Festival. These festivals often feature local talent, live performances, food trucks, and cultural displays. If you’re passing through St. Louis during one of these events, you’ll get a great mix of art, culture, and entertainment.

When: February/March.
What to Expect: St. Louis celebrates Mardi Gras with a massive street festival. It includes parades, costumes, live music, and food, making it a lively stop along your Route 66 journey. While it’s not a traditional "Route 66" festival, it’s a fun and festive way to experience the lively spirit of the region.

When: September.
What to Expect: Many small towns along Route 66, including towns like Joplin, Carthage, and Springfield, celebrate Labor Day with local festivals, live music, fireworks, and fairs. These festivals are a great way to experience community spirit and local traditions.

Check Festival Dates: Make sure to plan your route according to the festival dates, as they can vary yearly. Many of these festivals are annual, but the exact timing can shift.
Pack for the Weather: Depending on the festival, you might be outdoors, so make sure to bring comfortable clothing, sunscreen, and water. Missouri summers can be hot, and some festivals take place in the sun.
Plan for Crowds: Popular festivals like those in St. Louis and Springfield can attract large crowds, so be prepared for busy streets and lots of people, especially if you're attending a parade or a major event.
Consider Lodging: Festival weekends can fill up hotels quickly, so be sure to book your accommodations early, especially in larger cities like St. Louis and Springfield.

Wandering Souls