Sep
19
to Oct 11

Sunday River Brew Fest

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.

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Sep
20
to Sep 26

Farmington Fair

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.

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Sep
25
to Sep 27

Common Ground Country Fair

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.

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Sep
27
to Oct 3

Cumberland Fair

Celebrating its 154th 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.

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Oct
2
to Oct 4

Freeport Fall Festival

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!

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Oct
4
to Oct 11

Fryeburg Fair

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.

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Oct
10

Swine & Stein Brewfest

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.

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Oct
11

Damariscotta Pumpkin Boat Regatta

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.

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Oct
15
to Oct 17

Harvest on the Harbor

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.

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Oct
17

Harvest Fest

A free family-friendly festival that features live music, various local craft and food vendors, and activities for all ages.

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Oct
23
to Oct 25

Ogunquit Fest

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.

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Aug
13
to Aug 22

Skowhegan State Fair

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.

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Sep
27
to Oct 5

Fryeburg Fair

  • 1154 Main Street Fryeburg, ME, 04037 United States (map)
  • Google Calendar ICS

The Fryeburg Fair features the best of farming traditions and agricultural history, competitions, horse pulls, show horses, horse racing, oxen, steer, goats, pigs, poultry, rabbits, sheep, Woodsmen's Field Day, Firemen's Muster, Grand Parade, rides, food & entertainment. Every day at Fryeburg Fair offers a multitude of options for every age and it's all outlined on their website. Be sure to check out their Facebook & Instagram pages.

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Sep
21
to Sep 27

Cumberland County Fair

  • 197 Blanchard Road Cumberland, ME, 04021 United States (map)
  • Google Calendar ICS

The Cumberland Fair is a long-standing autumn tradition showcasing livestock competitions, agricultural exhibits, and demonstrations of Maine’s rural heritage. Visitors can also enjoy carnival rides, games, live entertainment, and an array of classic fair foods, making it a vibrant family-friendly event. Visit their website for more information.

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Sep
19
to Sep 21

Common Ground Fair

  • 294 Crosby Brook Road Unity, ME, 04988 United States (map)
  • Google Calendar ICS

The Common Ground Fair is the Maine Organic Farmers and Gardeners Association’s (MOFGA) annual celebration of rural living featuring 1000-plus exhibitors and speakers, and emphasizes vibrant communities, sustainable living and local economies, while highlighting organic agriculture. Click here to learn more.

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Sep
14
to Sep 20

Farmington Fair

  • 292 High Street Farmington, ME, 04938 United States (map)
  • Google Calendar ICS

The Farmington Fair highlights the state’s agricultural roots with livestock shows, produce displays, and traditional craft demonstrations. Visitors can also enjoy carnival rides, games, live entertainment, and a variety of classic fair foods, creating a festive late-summer experience for all ages. Visit their website to learn more.

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Sep
10
to Sep 13

Oxford County Fair

  • 67 Pottle Road Oxford, ME, 04270 United States (map)
  • Google Calendar ICS

The Oxford County Fair celebrates the region’s agricultural heritage with livestock exhibits, produce displays, and hands-on demonstrations of traditional skills. Fairgoers can also enjoy carnival rides, games, live entertainment, and a wide variety of classic Maine fair foods. Visit their website to learn more.

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Aug
23
to Sep 1

Windsor Fair

  • 82 Ridge Road Windsor, ME, 04363 United States (map)
  • Google Calendar ICS

The Windsor Fair is one of the state’s largest agricultural fairs, featuring livestock shows, produce displays, craft exhibits, and demonstrations of traditional farming skills. Visitors can also enjoy carnival rides, games, live music, and plenty of classic fair foods, making it a lively end-of-summer tradition for families and fairgoers alike. Visit their website for more information.

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Aug
21
to Aug 24

Acton Fair

  • 550 Maine 109 Acton, ME, 04001 United States (map)
  • Google Calendar ICS

A classic late-summer agricultural fair featuring livestock shows, produce displays, and demonstrations of traditional farming skills. Visitors also enjoy carnival rides, games, live entertainment, and plenty of Maine’s favorite fair foods, making it a fun-filled tradition for families and fairgoers alike. For more information, visit their website.

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Aug
7
to Aug 16

Skowhegan State Fair

  • 33 Constitution Avenue Skowhegan, ME, 04976 United States (map)
  • Google Calendar ICS

A classic late-summer agricultural fair featuring livestock shows, produce displays, and demonstrations of traditional farming skills. Visitors also enjoy carnival rides, games, live entertainment, and plenty of Maine’s favorite fair foods, making it a fun-filled tradition for families and fairgoers alike. For more information, visit their website.

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