Ultimate Guide to Maine’s Best Fall Fairs and Festivals 2025
Crisp air, colorful leaves, and the scent of fried dough — Maine’s fall fairs and festivals fill every corner of Maine with nostalgic joy. From pumpkin regattas to prize-winning livestock and local crafts, these autumn events celebrate everything we love about Maine. Grab your sweater and join the fun — there is so much fun to be had!
In this blog post, we share the history of fairs and festivals in Maine, a list of the must-see fairs and festivals, insider tips for fair first-timers, and a monthly calendar of all the fairs and festivals to help you spend less time planning and more time enjoying!
History of Maine Fall Fairs and Festivals
Maine’s fall fairs and festivals began in the early 1800s as small agricultural gatherings where farmers showcased livestock, crops, and skills—with the Skowhegan State Fair among the first. By the mid- to late-19th century, these events expanded into major social occasions, adding midway attractions, horse racing, and food stalls. Maine’s rich Fall harvest and foliage helped our fairs evolve into full-fledged fall festivals during the 20th century, blending traditional agriculture with crafts, music, parades, and local food. Signature events such as the Fryeburg Fair, Common Ground Country Fair, and Damariscotta’s Pumpkinfest illustrate how Maine preserves its agricultural heritage while embracing modern entertainment and tourism, making fall the state’s peak season for community celebrations.
The Best Maine Agricultural Fall Fairs in Maine
Date: September 27th-October 5th
Location: Fryeburg, Maine
Maine’s largest agricultural fair is an annual event that families look forward to all year long. Offering a non-stop rotation of demonstrations, food vendors, entertainment, and activities for all ages—there is something for everyone to enjoy at the Fryeburg Fair.
Date: August 7th-16th
Location: Skowhegan, Maine
The Skowhegan State Fair is one of Maine’s oldest and most celebrated agricultural fairs. Known for its livestock competitions, showmanship events, horse pulling, harness racing, and iconic fair food—it’s a quintessential state fair.
Date: September 19-21st
Location: Unity, Maine
The Common Ground Country Fair is a unique celebration of sustainable living and local agriculture, offering a rich array of artisan craft demonstrations, hands-on workshops, live music, and plenty of fresh-baked treats and eats. With its emphasis on sustainability, local craftsmanship, and community engagement—the Common Ground Country Fair offers an enriching and immersive Maine festival experience unlike any other.
Date: September 21st-27th
Location: Cumberland, Maine
Celebrating its 153rd season, the Cumberland Fair is an autumn tradition that blends agricultural heritage with family-friendly fun. Fair goers can enjoy livestock shows, including cattle, sheep, and poultry competitions, alongside exhibits of pumpkins, produce, and crafts that celebrate the region’s farming roots. With its mix of hands-on activities, delicious local foods, and vibrant events, the Cumberland Fair offers a quintessential Maine fall experience for the whole family.
Date: September 14th-20th
Location: Farmington, Maine
The Farmington Fair is a classic celebration of the state’s agricultural traditions, offering a lively mix of events, food, and activities for all ages. Visitors can explore livestock exhibitions, including dairy cows, goats, and poultry, alongside displays of pumpkins, produce, and crafts that highlight local farming and artisan skills. With its combination of agricultural showcases, tasty local foods, and hands-on activities, the Farmington Fair offers a warm and festive taste of Maine’s fall culture.
The Best Fall Festivals in Maine
Date: October 24-26th, 2025
Location: Ogunquit, Maine
OgunquitFest is a beloved fall celebration held every October. The festival features a classic car show, a huge artisan craft fair, children’s games, and a wildly popular costume parade alongside pumpkin and scarecrow displays. Visitors also enjoy seasonal treats, live entertainment, and coastal foliage views, making it a perfect way to experience Maine’s fall spirit by the ocean.
Date: October 11th, 2025, 12-5:00p.m.
Location: Gardiner, Maine
Gardiner’s Swine & Stein Brewfest features samples from some of Maine’s best breweries, wineries and distilleries in an open air beer garden along historic downtown Water Street. Visitors can enjoy hours of great live music, local food trucks, and fun events—such as the highly competitive Beard and Mustache Competition.
Damariscotta Pumpkin Boat Regatta
Date: October 12th at 4:00p.m.
Location: Damariscotta Municipal Parking Lot
One of Maine’s most unique events—the pumpkin boat regatta provides all ages with endless laughs and entertainment. Watch as “pumpkin captains” try and steer their giant gourd down the Damariscotta River in a series of races that are sure to leave you wanting more. The regatta can be viewed harbor-side, or via a “live feed” into The Lincoln Theater, where spectators are able to watch the event, seated in the warmth and comfort of the historic theater.
Freeport Fall Festival (Freeport)
Date: October 3rd-5th
Location: Freeport, Maine
Each year on the first weekend in October, Visit Freeport brings together over 225 of the best New England artists, makers and local food producers for a free, three-day festival in downtown Freeport that features live music, activities for kids, and more!
Date: October 30th-November 1st
Location: Maine Studio Works, 170 Anderson St., Portland, ME 04101
Portland’s one and only food and drink festival—Harvest on the Harbor brings together and showcases local restaurants, craft breweries, distillers, cheesemakers, aquaculturists, and hospitality experts from across Maine.
Date: September 20th-October 12th
Location: Sunday River, Newry, Maine
Four weekends of craft beer tasting, live music, scenic lift rides, contests, competitions, and a craft fair—all taking place amongst a beautiful, foliage-filled backdrop.
Date: October 18th 9a.m.-4:00p.m.
Location: York, Maine
A free family-friendly festival that features live music, various local craft and food vendors, and activities for kids.
Complete Calendar of Maine Fairs & Festivals Fall 2025
Insider Tips for Visiting Maine Fairs & Festivals
Bring cash
Paid parking and entrance fees at fairs are usually cash only (sometimes they accept Venmo). Some food, craft, and ride vendors may only accept cash too, so it’s always a good idea to have cash on hand.
How to avoid crowds
Fairs and festivals tend to be less busy in the mornings and on week days. If possible, buy your admission tickets and ride tickets ahead of time so you don’t have to spend time waiting in line.
Parking and transportation tips
Do your research beforehand so you’re not left wondering where to park. The websites linked above all provide parking information.
What to wear
Comfortable footwear and several layers of clothes, as temperatures in Maine can fluctuate between 50-degrees and 80-degrees all in the same day.
Arrive early
Seating for popular events or demonstrations, such as horse pulling or horse racing tend to fill up quickly. Try and arrive 20-30 minutes beforehand to get a decent seat.
Leave no Trace at Maine’s Fall Fairs + Festivals
When it comes to enjoying time at Maine fairs and festivals, remember the golden rule: Leave No Trace. It’s as simple as throwing away your garbage, recycling any bottles you use, respecting fair property, and leaving nothing but footprints.
Interested in more Maine Fall travel content? Check out our posts about Maine Fall foliage hikes and Maine Fall weekend itineraries and guides.
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