Booth Bay Harbor Fest - Boothbay Harbor, ME - Sep 4 to Sep 7, 2020
A celebration of local food and live music on the waterfront.
Freeport Fall Festival - Freeport, ME - Oct 2 to Oct 4, 2020
A three day festival showcasing New England artists and craft makers on the L.L.Bean campus and downtown Freeport, plus live music, Chodwah Challenge, food, and more!
Damariscotta Pumpkinfest & Regatta - Damariscotta, ME - Oct 3 to Oct 12, 2020
Pumpkinboats (400-700 pound, hollowed out pumpkins) are paddled or motor powered in this famous regatta on the Damariscotta River. Also includes giant pumpkin weigh-off, parade, pumpkin drop, pumpkin pancake breakfast and other activities. Main events are over Columbus Day Weekend. In 2017, Travel and Leisure called this one the “Best Fall Festival in Maine!” (https://goo.gl/W3Pdse)
Fryeburg Fair - Fryeburg, ME - Oct 4 to Oct 11, 2020
Livestock exhibition, parade, competitions like the Fireman’s Muster and the Skillet Throw, midway rides and carnival games. Admission is $12 a day.
Sunday River Fall Festival Weekend - Newry, ME - Oct 10 to Oct 11, 2020
North American Wife Carrying Championship, kids’ pumpkin pie eating contest, New England corn hole championship, Blue Mountain Arts and Crafts Fair. wine tent, Sunday Bloody Sunday tent. Concerts on Saturday and Sunday. Scenic chairlift rides to the Peak Lodge, free wagon rides and more.
Pemaquid Oyster Festival - Damariscotta, ME - Sep 26 to Sep 26, 2021
More than 10,000 oysters are served annually at this event to benefit the Edward A. Myers Marine Conservation Fund. Held on the banks of the Damariscotta River at Schooner Landing Restaurant & Marina. Other food options available. There is also an entertainment stage, educational exhibits and other locations. Noon to dusk, rain or shine.