When: Annually in September
The Route 66 Rendezvous in San Bernardino is a must-attend for festival lovers. This annual event celebrates the iconic highway with a massive car show featuring hundreds of classic and vintage vehicles, live music performances, and a festive parade. It’s a family-friendly event with something for everyone—whether you’re into cars, music, or good food.

When: Annually in May
For a traditional fair experience, the San Bernardino County Fair is a fun stop along Route 66. This festival offers rides, games, livestock shows, and local food vendors. It’s an excellent event for families, food lovers, and anyone who enjoys the carnival atmosphere.

When: Annually in May
The California Route 66 Classic Car Show in Barstow is a celebration of classic cars, trucks, and motorcycles. This festival showcases vintage vehicles and features live music, food trucks, and a parade down Main Street. If you’re a car enthusiast, this is a fantastic opportunity to enjoy both the cars and the community atmosphere.

When: Annually in October
The High Desert Music Festival in Joshua Tree is perfect for music lovers. Held in this iconic desert town, the festival features live performances by a wide range of musicians, from indie and rock to country and folk. The music is complemented by arts and crafts booths, food vendors, and plenty of outdoor fun. The desert setting makes it a unique festival experience.

When: Annually from late September to October
Big Bear Lake’s Oktoberfest is one of the best-known fall festivals in Southern California. While it’s a bit off Route 66, it’s worth the short detour for anyone traveling along the highway. Celebrate Bavarian culture with beer, bratwurst, traditional German music, and games. It’s a lively and fun event, ideal for festival-goers who love food, drink, and community celebrations.

When: Annually in May and October
The Joshua Tree Music Festival is a wonderful, intimate gathering in the Mojave Desert. This festival focuses on family-friendly music, yoga, and wellness. It features a diverse lineup of bands and solo acts across a variety of genres, including folk, indie, and world music. Set against the stunning desert backdrop of Joshua Tree, it’s a peaceful festival perfect for those looking for both relaxation and rhythm.

When: Annually in September
The California Native American Day in San Bernardino celebrates the rich culture and traditions of Native American communities. The event features music, dance performances, arts and crafts, and educational activities. It's a wonderful way to learn about the indigenous peoples of California while enjoying traditional ceremonies and performances.

When: Annually in the summer
For festival-goers interested in aerospace and aviation, the Mojave Air & Spaceport Festival is a unique event. This festival celebrates the aviation and space industries with exhibits, aircraft displays, and live demonstrations. You can see historic aircraft up close and experience the excitement of space travel, all while enjoying food and live entertainment.

When: Annually in December
The Festival of Lights is a magical event that marks the holiday season in San Bernardino. With hundreds of thousands of lights decorating the city, parades, and holiday performances, it’s a great family-friendly event to experience the holiday spirit while on your Route 66 journey. There are also food vendors and live entertainment to enjoy.

When: Annually (dates vary)
The Route 66 Music Festival is a traveling music festival that often stops in towns along Route 66 in California. The event includes a mix of genres, featuring local and regional musicians. Whether you’re into rock, blues, or country, you’ll find live performances in small towns along the historic route.

When: Annually in May
While not directly on Route 66, the California Strawberry Festival is a major food festival located just a short detour off the highway in Oxnard. The event celebrates everything strawberry, with food tastings, music, and carnival rides. If you're a foodie, this is a festival not to be missed.

When: Annually in September
The Los Angeles County Fair in Pomona, just a short drive from Route 66, is one of the largest fairs in California. It’s a full-scale celebration of food, rides, animals, music, and live entertainment. The fair’s variety of shows, games, and contests makes it a great choice for families and festival lovers alike.

When: Annually in April
While Coachella is a bit farther from the Route 66 path, it's one of the biggest music festivals in California and an easy detour if you’re driving through the desert. Known for its eclectic mix of artists and amazing performances, Coachella is a top event for music lovers, offering a unique festival experience with art, fashion, and food to boot.

When: Annually in June
The Temecula Valley Balloon & Wine Festival combines two major attractions: hot air balloons and wine. While Temecula is a bit off Route 66, it’s well worth the detour for festival-goers. This festival features hot air balloon rides, wine tastings, live music, and delicious food.

When: Annually in September
The California Folk Festival in San Bernardino brings together folk musicians from all over the country for a weekend of music, art, and culture. It’s a great event for those who appreciate acoustic and folk music in a relaxed outdoor setting.

Check Schedules: Festival dates may vary from year to year, so be sure to check the event’s official website or local listings to plan your trip accordingly.
Book in Advance: Many popular festivals, especially in larger cities like Los Angeles or San Bernardino, require booking accommodations early, as these events often attract large crowds.
Pack for the Weather: Depending on the time of year and your festival choice, you may encounter desert heat, cool mountain temperatures, or coastal breezes. Be sure to bring appropriate clothing and sunscreen!

Wandering Souls