The 10 Best Fall Festivals in Maine!

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Now that the kids are back in school, the days are getting cooler, and the leaves are starting to change. The official start to fall is here and that means an explosion of pumpkin spice everything, apple picking, and warm sweaters. Throughout the state of Maine, you’ll find these 10 awesome festivals celebrating the change in season! 

1. Fryeburg Fair, Fryeburg, ME

The Fryeburg Fair, Maine’s oldest and largest fair, marks the end of fair season in Maine. Established in 1851, the Fryeburg Fair is considered to be one of the best agricultural fair in the country. Running for a week, you have eight days to enjoy the animals, exhibitions halls, cooking contests, rides, and more. People come from all over Maine and New England to enjoy this classic Maine tradition.

2. Annual Fall Foliage Festival, Boothbay Harbor, ME

Every Columbus Day weekend the Museum’s Village Green in Boothbay Harbor is transformed in a fall marketplace with dozens of vendors selling handmade crafts and delicious local foods. A ride on the Boothbay Railroad is a great way to explore the historic buildings and see the incredible fall foliage of the region. Kids can enter the pumpkin carving contest and more.

3. Damariscotta Pumpkinfest & Regatta, Damariscotta, ME

The Damariscotta Pumpkinfest & Regatta is a mid-coast Maine favorite. Happening over Columbus Day weekend, you’ll find a host of events for the whole family. Start the weekend off with the official “Giant Pumpkin Parade” followed by lots of fun events like the Pumpkin Debry, Pumpkin Catapult, and Pumpkin Regatta. Watch while people race their pumpkin boats down the river for the coveted “Golden Gourd” trophy. 

4. Freeport Fall Festival, Freeport, ME

The Freeport Fall Festival is a weekend fall festival celebrating art, fine craft, and live music. There are always great bands playing on L.L. Bean’s Discovery Stage and you’ll find some of the best artists and fine craft markers throughout New England at this event. There’s face painting and bubble making for the kids and plenty of food vendors, too. 

5. Sunday River Fall Festival, Newry, ME

Sunday River’s annual fall festival is the unofficial kickoff to winter. While there won’t be any snow, you will find lots of fun family-friendly events and activities all weekend. Don’t miss the Annual North American Wife Carrying Championship. There is a music festival, the annual Blue Mountain Arts and Crafts Fair, and even a corn hole championship. For the adults, there is a wine and “Sunday Bloody Sunday” tent if you need an adult beverage. 

6. Pineland Farms Harvest Festival, New Gloucester, ME

The annual Pineland Farms Harvest Festival has loads of fun for families and children of all ages. Located less than an hour from Portland, the Harvest Festival has a Farmers Obstacle Course, a corn maze, face painting, and more. There is even a complimentary showing of “It’s the Great Pumpkin, Charlie Brown.”

7. Common Ground Country Fair, Unity, ME

Every September over 60,000 people visit the Common Ground Country Fair in Unity. Featuring demonstrations, organic Maine food products, local crafts, and more, this popular fair celebrate the rural life many Mainers choose to live. Throughout the weekend there is a 5K running race, draft horse show, and sheep dog demonstrations. 

8. Acadia’s Oktoberfest, Southwest Harbor, ME

Maine is well known for its craft beer and what better way to celebrate than with Oktoberfest! Acadia’s Oktoberfest is a two-day celebration with a wine tasting on one day and brewfest on the other. There will be beer from some of Maine’s best breweries along with food, games, and live entertainment. 

9. Annual Cornish Apple Festival, Cornish, ME

Cornish might be a small western Maine town, but its population explodes every year on the Annual Cornish Apple Festival. This free festival features over 50 arts and crafts vendors, live entertainment from local performers, annual apple pie baking contest and more. Head down the street to Apple Acres Farm for the annual Bluegrass Gathering. 

10. Maine Lakes Brewfest, Casco, ME

Fall might be all about pumpkins and apples, but Germany’s tradition of Oktoberfest is quite popular in beer loving Maine. The Annual Maine Lakes Brewfest is a popular event at Point Sebago Resort on the shores of Sebago Lake. This 21-plus day festival features beer from over 35 local breweries, 14 food vendors, and live music. You even leave with a souvenir sampling glass. 

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