10 Fun Maine Fall Events For 2024

Maine’s 2024 fall season is packed with exciting events, with various experiences that celebrate the state’s vibrant autumn traditions. Between the Common Ground Fair, the Fryeburg Fair, and more than one pumpkin festival, there’s something for everyone—from culinary delights and live music to outdoor adventures and family-friendly activities across the state.

Common Ground Country Fair

Hosted by the Maine Organic Farmers and Gardeners Association, this get-together at the fairgrounds in Unity highlights Maine’s rural and agricultural traditions with animal exhibits, cooking demos, blacksmithing, farm and fiber marketplaces, tasty food, and kids’ programming. Headed to a different part of the state? Check out a master list of Maine Agricultural Fairs.

Damariscotta Pumpkinfest & Regatta

A giant pumpkin contest, pumpkin parade, pumpkin drop —perhaps you’re detecting a theme? Don’t miss the great pumpkin boat regatta finale.

Trails End Festival

This family-friendly, annual Maine fall festival started 15 years ago in celebration of the Katahdin region, the Appalachian Trail’s end. The festiva offers fun for the whole family including face painting, hiking, a chili cook-off, vendors, a parade, and games. A festival-favorite event is the Rubber Duck Race!

Blue Hill Fair

This “down to earth” fair was the model for the one in E.B. White’s Charlotte’s Web, and to this day, a special tent holds all the animals from the book (which was written in nearby Brooklin). The rides, farm exhibits, and fair foods that Charlotte and Wilbur’s human friends enjoyed are here, along with sheepdog trials that draw competitors from all over.

Cumberland County Fair

Turning 150 this year, southern Maine’s biggest fall festival packs in events as diverse as truck and tractor pulls, a rodeo, a demolition derby, nightly fireworks, and 10 live-music acts spanning blues to bluegrass and everything in between. And who needs pies when there’s a burrito-eating contest?

Boothbay Fall Foliage Festival

Boothbay’s fall event takes place on handsome four-acre town green, done up as a “vintage village” featuring art exhibits, food trucks, booths selling local crafts, live music, and a children’s corner. Take a ride on a steam-powered train at Boothbay Railway Village, and visit the adjacent antique car museum.

Farmington Fair

Central Maine’s big September event delivers the expected—a lively midway, tractor and horse pulls, lots of good fair chow—plus events including harness racing, an ugly veggie contest, and a “Drag Your Neighbor” competition, where you can floor your ride without getting a speeding ticket.

Fryeburg Fair

Since its start in 1851, western Maine’s harvest fest has grown into an eight-day celebration of the region’s farms, gardens, foods, and crafts. Midway rides and oxen pulls, calf and pig “scrambles,” and an anvil-throwing contest vie for popularity with midway rides and a farm museum, and the Woodsmen’s Field Day draws loggers from across the U.S. to test their mettle.

Harmony Free Fair

Yes, it’s free. And for a town with fewer than a thousand folks, Harmony stages a surprisingly big event. Along with local music acts and traditional agricultural and animal exhibits, the accent is on friendly competition, with tournaments in volleyball, cornhole, arm wrestling, horseshoes, skillet and hammer throwing, and even cribbage. And it all ends with a big Labor Day parade.

New Portland Lions Fair

Up near Skowhegan, far from the “old Portland,” the local Lions pair their midway, food booths, and agricultural attractions with plenty of lively competitions, such as wrestling matches, a demolition derby, and a kids’ “eel race,” done on hands and knees with participants holding on to their teammates’ ankles.