10 Best Outdoor Festivals in Massachusetts

By Kimberly Ripley

10 Best Outdoor Festivals in Massachusetts

Massachusetts is a melting pot of activities for all outdoor enthusiasts. Whether you love to experience nature and thrills from the land or in the water, Massachusetts probably has a festival for it. Pursue your outdoor passions at these 10 best outdoor festivals and events in Massachusetts. 

1. StrangeCreek Campout, Greenfield, MA

This three-night camping event is the biggest party in the woods this year. Come for the day or stay for the weekend as you enjoy live music, a fire show, yoga, a bonfire, puppets, and more. There are tons of ways to camp, including family style camping, tent, RV, or even your car! Included in the lineup are Melvin Seals and JGB, The Machine, Max Creek, Ryan Montbleau, and Zach Deputy, among others.

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2. Tour de Fat, Boston, MA

Sponsored by New Belgium Brewing Company and its signature Fat Tire beer, this beer and bike festival is the most fun you’ll ever have on two wheels. It started as an effort to raise money for local bike non-profits, and it’s still going strong after 19 seasons. Live music and entertainment and plenty of bike riding are reason enough to celebrate, but the real crowning jewel is that your ticket helps to fund the Boston Cyclists Union in their mission to help others enjoy bike riding. 

3. DemoFest, Charlemont, MA

Happening at Zoar Outdoor is one of the biggest kayaking celebrations in the state. This epic party is an outdoor thrill seeker’s dream come true, offering activities for paddlers of all skill levels. Kayakers can test out the best new whitewater boats and enjoy free instruction and mini clinics. The event is 100 percent free to all and spans three days of wild, wet fun.

4. Muckfest, Ayer, MA

This nationally-acclaimed mud run is coming to Massachusetts, and you’ll never enjoy getting this dirty anywhere else. This 5K race is chock full of fun, challenging obstacles, and you can choose to enlist a team or go it alone. There’s a party waiting for you when you finish, win or lose, so do your best and enjoy this outdoors fest.

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5. Trail Fest, Littleton, MA

Enjoying the outdoors doesn’t always require high energy. For a more laid back approach, head to Trail Fest at George and Lucy Yapp Conservation Land. Start the morning with yoga and stretching, them embark on guided trail walks before ending your event with a cookout. There will also be activities for the younger crowd, including a petting zoo, so make sure you bring the whole family for a day with nature.

6. Wild Fish Open Water Swim Festival, Salem, MA

If you’ve ever been told you’re a fish in the water, it’s time to put your money where your mouth is and join the swim. With three distances (one mile, 1.5 miles, and two miles), this event puts 200 swimmers in the water to see who can keep up with the fishes—and who will be left behind for shark bait! (Just kidding). This swimming race takes place in scenic Salem Harbor, and there’s no other event in the state like it.

7. Nantucket Race Week, Nantucket, MA

This unique collection of regattas spans nine days and puts hundreds of boats in the water. Enjoy a day on the water as boats race to cross the finish line. There’s a special kiteboarding regatta, as well as events just for youth. Hosted by the Nantucket Yacht Club and the Great Harbor Yacht Club proceeds will benefit the Nantucket Community Sailing non-profit organization. 

8. BikeFest, Florence, MA

Touted as the most fun you will have off or on a bike, this Bike Fest is more than just a ride around town. Live music, better-than-fair food, beer, and other entertainment abounds at every angle. Hosted by the Northampton Cycling Club, the festival features rides for all skill levels and ages. 

9. Redbones Bike Party, Somerville, MA

If you love all things cycling, you won’t want to miss the best bicycle part in MA. There’s always plenty of food and beer to go ‘round, plus you can explore the bike expo while you party. Your ticket grants you access to the raffle, valet parking, food, and drink—it’s almost like they’re paying you to come.

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10. Franklin Park Kite and Bike Festival, Boston, MA

Taking place on the beautiful Franklin Park Golf Course, this outdoor event combines two favorite activities: kite flying and biking. Dozens of colorful kites fill the sky to create an array of flying merriment. You can bring your bike to ride through the park, participate in a kids-only bike rodeo, or join a guided group tour. Bikes Not Bombs will be on site for bike repairs and tune ups. It’s a casual, informal event that has no rhyme or reason other than to get you off the couch and into the sunshine. 

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