10 Must-Visit Fall Festivals in Maine You Can’t Miss

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As the air turns crisp and the leaves transform into brilliant hues of red, orange, and gold, Maine comes alive with vibrant fall festivals that celebrate everything this beautiful season has to offer. From pumpkin festivals to cider tastings, there’s no shortage of ways to enjoy autumn in Maine. Whether you’re a local or just visiting, these fall festivals are must-attend events that capture the heart of Maine's autumn charm.

1. Damariscotta Pumpkinfest & Regatta

Perhaps the most iconic fall event in Maine, the Damariscotta Pumpkinfest & Regatta is a quirky celebration of all things pumpkin. Held in the coastal town of Damariscotta, this festival is famous for its giant pumpkin boat races, where participants carve out enormous pumpkins and race them across the water. In addition to the regatta, there’s a pumpkin parade, pumpkin-themed food, and even pumpkin catapulting! This family-friendly event is a highlight of the fall season.

2. Freeport Fall Festival

For lovers of art, food, and local crafts, the Freeport Fall Festival is the perfect fall weekend getaway. Located in the charming town of Freeport, home to L.L.Bean’s flagship store, this festival showcases over 150 artists and craftspeople from across New England. In addition to perusing handmade goods, you can enjoy live music and indulge in delicious Maine fare from local food trucks. The Freeport Fall Festival is a great way to spend a leisurely day soaking up the fall atmosphere.

3. Sunday River Fall Festival

If you’re looking for a mix of outdoor adventure and fall fun, the Sunday River Fall Festival in Newry is the place to be. Set against the backdrop of the stunning Sunday River Ski Resort, this festival offers everything from scenic chairlift rides to the annual North American Wife Carrying Championship—a lighthearted competition where couples race through a challenging obstacle course. The festival also features live music, a craft fair, and a Bloody Mary and chili cook-off to keep you warm and entertained.

4. Fryeburg Fair

One of the most beloved and longest-running fairs in Maine, the Fryeburg Fair is an autumn tradition dating back to 1851. This week-long agricultural fair is held every October and draws visitors from all over New England. With livestock exhibitions, harness racing, a midway full of rides, and endless food stalls serving up classic fair treats, there’s something for everyone at Fryeburg Fair. It’s the quintessential Maine fall experience.

5. York Harvestfest & Kidsfest

For families with children, the York Harvestfest & Kidsfest is the perfect way to enjoy a fall day. Held annually in York Beach, this festival offers a mix of live entertainment, food vendors, and local crafts, all while catering to younger visitors with activities like face painting, pumpkin decorating, and games. It’s a wonderful way for families to celebrate the season together while enjoying Maine’s coastal beauty.

6. Great Maine Apple Day

If apples are more your style, then the Great Maine Apple Day in Unity is a must. This one-day event celebrates all things apple, from cider pressing demonstrations to apple tastings. Hosted by the Maine Organic Farmers and Gardeners Association (MOFGA), the festival focuses on the importance of heirloom apples and organic farming. You can sample apple varieties, learn about sustainable growing practices, and even take home fresh apples from local orchards.

7. Harvest on the Harbor

Maine’s vibrant food scene takes center stage at Harvest on the Harbor in Portland, one of the state’s premier culinary festivals. This multi-day event celebrates Maine’s top chefs, farmers, and artisans with tastings, cooking competitions, and gourmet dinners. It’s a food lover’s dream, offering a unique opportunity to experience Maine’s farm-to-table movement while enjoying the best local seafood, cheeses, and fall harvest ingredients.

8. Acadia Oktoberfest

Set in the stunning Acadia National Park region, Acadia Oktoberfest offers a taste of Germany with a Maine twist. This popular beer and music festival features brewers from across the state, serving up local craft beers alongside traditional German foods like bratwurst and pretzels. The festival also includes live music, arts and crafts vendors, and activities for kids, making it a great event for all ages. Plus, it’s the perfect way to enjoy the breathtaking fall foliage around Acadia.

9. Common Ground Country Fair

Organized by the Maine Organic Farmers and Gardeners Association (MOFGA), the Common Ground Country Fair in Unity is a celebration of rural life, sustainable living, and Maine’s agricultural heritage. Held every September, this three-day fair features everything from organic farming workshops to fiber arts demonstrations. There’s also a farmers’ market, livestock displays, and live entertainment. It’s a true Maine experience that highlights the state’s commitment to organic farming and local food.

10. Bethel Harvestfest & Chowdah Cook-off

The town of Bethel welcomes autumn with its annual Harvestfest & Chowdah Cook-off. This fall festival celebrates the season with local crafts, a scarecrow-making contest, and, of course, a chowder competition featuring some of the best chowder Maine has to offer. With the stunning White Mountains as a backdrop, this festival is perfect for those looking to enjoy great food, local culture, and beautiful fall scenery.