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10 Best Fall Festivals in Maine

People love to visit Maine in the summer when blueberry and lobster festivals are in full swing. But autumn may give those warmer months a run for their money, as the weather is still nice, and an abundance of harvest festivals fill the calendar. If you’re looking to attend fall festivals in Maine, these picks are the best.

Damariscotta Pumpkinfest & Regatta, Damariscotta Damariscotta Pumpkinfest
Credit: Damariscotta Pumpkinfest by Chiot's Run via Flickr

Damariscotta Pumpkinfest & Regatta, Damariscotta

Damariscotta Pumpkinfest & Regatta is a multi-day celebration, largely about the art of growing pumpkins, which is fun and interesting to learn about. But it gets more outlandish, with giant hollowed pumpkins battling it out on the raceway or sailing the harbor! Humongous pumpkins are carved to decorate the streets of the small town, where a parade will precede, celebrating the biggest pumpkin of the season. Watch pumpkins smash, chow down on an array of pumpkin desserts, and participate in or spectate the pumpkin pie eating contest. And if you need one more reason to drop by, the occasion focuses on non-profit organizations. Side note— Damariscotta is highly touted for its fishing spots.

Dates: September 30th-October 9th, 2023
Official Website

York Harvestfest, York Harvestfest York Beach
Credit: Harvestfest York Beach by Yorkharvestfest.com

York Harvestfest, York

Harvestfest goes down in the York Beach area, which offers lovely scenery to soak in on chilly, sunny days of fall in Maine. Later in October, folks gather for an event with a simple enough theme—great food, shopping, carnival rides and games. Ride on a traditional wagon pulled by beautiful horses with flowers in their braided hair after browsing countless of vendors beneath the tents. Listen to live music as you indulge in a buttery lobster roll, lobster mac and cheese, whoopie pies, pumpkin donuts and blueberry treats galore.

Dates: October 14th, 2023
Official Website

Boothbay Fall Foliage Festival, Boothbay Boothbay Fall Foliage Festival Train Ride
Credit: Boothbay Fall Foliage Festival Train Ride by Railwayvillage.org

Boothbay Fall Foliage Festival, Boothbay

Boothbay Fall Foliage Festival is held at the Boothbay Railway Village, where attendees can hop aboard an old-fashioned, narrow-gauge steam train to kick things off. Further immersing into history, there will be interpretations of life in the past when the railway began to dominate in Maine. However, all the traditional festival goodies, from food, crafts, kids activities and music, are a part of the gathering. Set up on the Village Green, a four-acre grassy nook in the village, the Boothbay Foliage Fair takes place around mid-October.

Dates: October 7th-8th, 2023
Official Website

Maine Harvest Festival, Bangor Maine Harvest Festival goodies
Credit: Maine Harvest Festival goodies by Maine Harvest Festival

Maine Harvest Festival, Bangor

Maine Harvest Festival in Bangor truly does celebrate the harvest of hundreds of local farmers, as well as those who craft wholesome products regionally. While a total treat for the pallet, as wineries, distilleries and chefs bring their top game, there will also be an abundance of talented artists creating treasures and trinkets reminiscent of
“Vacationland.” Stop by quaint Bangor in November at the Cross Insurance Center, then explore the town that inspired Stephen King’s “It.”

Dates: November 18th-29th, 2023
Official Website

Freeport Fall Festival, Freeport Freeport Fall Festival
Credit: Freeport Fall Festival by Freeportfallfestival.com

Freeport Fall Festival, Freeport

The Freeport Fall Festival happens in early October and extends for three days straight. Freeport houses the massive flagship L.L. Bean campus, which is where things are centralized. Thousands flock to the adorable seaside town to taste the best foods of Maine while exploring the unique works of local artists. Music pipes through the streets as people browse the eclectic local shops and outdoor megastore. Yankee Candle is a particularly cozy stop on a fall day.

Dates: October 6th-8th, 2023
Official Website

Fall Festival at Sunday River, Newry Sunday River Resort
Credit: Sunday River Resort by Sundayriver.com

Fall Festival at Sunday River, Newry

Tired of the typical pumpkin patch picking and corn maze roaming? Come to the Fall Festival at Sunday River, where partners carry their significant others through a gritty obstacle course. Why? To win their partner’s weight in beer, of course. Aside from the silly shenanigans, there will be a New England cornhole tournament. But coming to Sunday River Resort during the fall is also peaceful and visually breathtaking, as the surrounding trees morph into bundles of yellow, orange and red. Scenic gondolas and lifts are in use despite the lack of snow, so festival attendees can see it all from up above.

Dates: October 7th-8th, 2023
Official Website

Harvest on the Harbor, Portland Harvest on the Harbor
Credit: Harvest on the Harbor by Harvestontheharbor.com

Harvest on the Harbor, Portland

Harvest on the Harbor brings killer eats, talented chefs and premium booze to the exciting streets of Portland. Going above the rest in the food department, the happening is a culinary celebration where you’ll hear lots of words like “epicurean” and “artisan.” Harvest on the Harbor connects world-renowned chefs with the local farmers, oyster growers, lobsterers and food masters of Maine to establish a harmoniously delicious event for the public. Whether you dine at one of the phenomenal dinners or brunches or just browse and snack at the market, your taste buds just can’t miss it.

Dates: October 25th-28th, 2023
Official Website

Acadia’s Oktoberfest, Mount Desert Acadia's Octoberfest
Credit: Acadia's Octoberfest by Acadiaoktoberfest.com

Acadia’s Oktoberfest, Mount Desert

In Southwest Harbor, the other side of the island in which Bar Harbor resides, is Acadia’s Invitational Oktoberfest. Focusing in detail on the things that make the “Quiet-side” special, this Oktoberfest offers a different Acadia National Park experience. The festivities last for a full ten days, so prepare to dive into an extensive beer scene while snacking on chocolates, kettle corn, gourmet grilled cheese as well as handmade sriracha sesame sausages, chowder and lobster.

Dates: October 6th-7th, 2023
Official Website

Camp Sunshine Maine Pumpkin Festival, Freeport Camp Sunshine Pumpkin Festival
Credit: Camp Sunshine Pumpkin Festival by campsunshine.org

Camp Sunshine Maine Pumpkin Festival, Freeport

L.L. Bean’s flagship megastore in Freeport is not only a super cool place to visit, with woodsy aesthetics, a cafe, an aquarium with an observation bubble and a diverse selection of goodies and gear, but they also host a charitable Halloween/fall event. Also known as Camp Sunshine’s Maine Pumpkin Festival, over 10,000 pumpkins flicker along the streets of the town. The sites of thousands of glittering orange beauties are enough to allure fall enthusiasts, but a parade, music and activities round out the experience.

Dates: October 21st, 2023
Official Website

OgunquitFest, Ogunquit Ogunquit, Maine
Credit: Ogunquit, Maine by Ogunquit Chamber of Commerce

OgunquitFest, Ogunquit

OgunquitFest typically takes place later in October—Ogunquit itself is the most precious, picture-perfect town with some really festive inhabitants. OgunquitFest builds off of the already present Halloween atmosphere, but there’s a lot of depth to this shindig. Go on a ghost tour, browse through classic cars, dote over and buy intricately handmade crafts and join in on the costume parade. If you’re looking to get into the Halloween spirit, you’re in luck here.

Dates: October 20th-22nd, 2023
Official Website

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