Riders on the vintage Pumpkin Patch Trolley at Seashore Trolley Museum in Kennebunkport. Book a ride through Oct. 18. (Courtesy of Seashore Trolley Museum)

With fall underway, we thought we’d take a moment from admiring the foliage to compile a list 14 can’t-miss events.
This year’s autumn awesomeness includes the Hurricane Meadows Fall Festival, the Freeport Fall Festival, Damariscotta Pumpkinfest & Regatta and the Swine & Stein Brewfest, among other happenings. Pull on your favorite flannel shirt and have at it.

9:30 a.m.-4:30 p.m. Friday to Sunday. Friday to Sunday. Through Oct. 18. Also on Oct. 12. Seashore Trolley Museum, 195 Log Cabin Road, Kennebunkport, $17, $15 for 60 and older and youths 6 to 16, $9 for ages 3-5, free for 2 and under. trolleymuseum.org.

The 28th annual Pumpkin Patch Trolley is underway at Seashore Trolley Museum. Hop aboard a heritage trolley for a ride to the pumpkin patch, where you can choose a favorite to take home. Back at the visitors center, supplies will be available for pumpkin decorating. The festivities also include a cookie walk, photo scavenger hunt, craft room and fall-themed photo backdrops. Costumes are encouraged.

10 a.m.-6 p.m. Friday to Sunday. Through Nov. 1. Also Oct. 12. Hurricane Meadows, 85 Hurricane Road, Falmouth, $15, free for under 2, $50 for season pass. hurricanemeadows.com.

People riding on the Bee Train makes their way between a corn maze and a pumpkin field at Hurricane Meadows in Falmouth on Nov. 1, 2025. (Gregory Rec/Staff Photographer)

The Hurricane Meadows Fall Festival features a Hearts of Pine-themed corn maze, gigantic jumping pillows, Bee Train rides around the farm, pick-your-own pumpkins and sunflowers, an immensely satisfying potato cannon, paintball range and much more. Be sure to grab a bag of warm apple cider donuts while you’re there. Face painting is available every Saturday and Sunday. Pumpkin Destruction day is Nov. 1, when visitors are invited to smash pumpkins with baseball bats and mallets and – weather permitting – pumpkins will be loaded onto a helicopter and dropped onto old cars.

Friday to Sunday. Downtown Freeport locations. visitfreeport.com.

The annual Freeport Fall Festival runs Friday to Sunday. (Photo courtesy of Visit Freeport)

Visit Freeport’s annual fall festival features more than 100 New England artists, makers and local food producers for three days. Exhibitors include Bloomside Botanicals, Fiddlewicks Candle Co. and New Moon Naturals among dozens of others. The live music lineup on multiple stages features singer-songwriter Eileen Rose, Americana and folk rock from The High Road and piano pop from Andrew Thomas, among acts from several genres. The festival also offers plenty of activities for kids, as well as multiple food options.

Saturday and Sunday. Statewide. mainecraftweekend.org.

Maine Craft Weekend is an annual chance for the public to get an inside look into the life and work of craft artists and businesses across the state. As you visit participating spots, you’ll encounter fellow craft enthusiasts and collectors during an educational, community-oriented and family-friendly weekend. Some of the locations are Karin Kraft in Cumberland Foreside, Resek Clay Studio in Camden, Maine Art Collective in Portland and Prescott Hill Pottery & Studios in Liberty. For a map of participating locations, head to mainecraftweekend.org/map.

Andrew Harris telling tales during the 2025 A Bizarre Victorian Bazaar: An Exhibition of Oddities and the Obscure at Victoria Mansion in Portland. (Photo courtesy of Victoria Mansion)

10 a.m. – 4 p.m. Saturday. Victoria Mansion, 109 Danforth St., Portland, $21, $8 college students, $6 for 6-17, free for 5 and under. victoriamansion.org.

The Bizarre Victorian Bazaar: Exhibition of Oddities and the Obscure is the annual gateway to Halloween season at Victoria Mansion. The day’s schedule includes learning about poison books and wallpaper, how purported mediums conducted seances and why some elite Victorians held mummy unwrapping parties. While you’re there, you can have your cards read, make Victorian crafts and enjoy a preview of Portland Ballet’s “Dracula” along with “Penny Dreadful” stories told by Andrew Harris and live music from One-Eared Cat. Sullivan House Bakery will be onsite with goodies.

Oct. 9 – 12. Main Street, Damariscotta. mainepumpkinfest.com.

Alice Andrenyak of Brunswick paddles a pumpkin during the 2025 Damariscotta Pumpkinfest & Regatta. (Derek Davis/Staff Photographer) Purchase this image

This beloved tradition features a pumpkin pancake breakfast, pumpkin dessert contest, assorted buskers, food court, pumpkin parade, pumpkin derby, kid’s zone, pie-eating contest, pumpkin hunt and other activities. Best of all is the Pumpkinboat Regatta at noon on Oct. 11. Watch giant carved-out pumpkins that have been crafted into boats race – and sometimes sink. View the spectacle from along the harbor or catch the livestream at the Lincoln Theater.

Oct. 10. Water Street, Gardiner, $45, $10 non-drinker/designated driver, $55 VIP. swineandsteinbrewfest.com.

The 2024 Swine and Stein event in Gardiner. (Anna Chadwick/Staff Photographer) Purchase this image

Beer, food, music and merriment take over downtown Gardiner at the annual Swine & Stein Brewfest. Sample your way through a lineup of more than 20 breweries, wineries, distilleries and mead producers. Live music will be performed by Katie Daggett, Hello Newman and The Delta Knights. Be sure to find a good spot to cheer during the frozen T-shirt race; Rock, Paper, Scissors Championship; and the beard and moustache competition.

Oct. 10-11. Boothbay Railway Village Museum, 586 Wiscasset Road, Boothbay, $5, free for 5 and under, $5 train rides. railwayvillage.org.

Customers shop at the 2025 Fall Foliage Festival at the Boothbay Railway Village Museum. (Brianna Soukup/Staff Photographer)

The Fall Foliage Festival is closing in on 60 years at Boothbay Railway Village. The two-day event features a local, vintage and handmade vendor fair with more than 80 artists and makers. You can also explore the antique car museum and model railroad, visit with the village goats and enjoy a train ride. Saturday’s live music will be from Justin Merle, The Newell Family Band and Catfish Brown. Sunday’s lineup is Owen Kennedy and the Hallowell Community Band.

Oct. 10. South Ridge at Sunday River, Newry. sundayriver.com.

A team get through the course of the 2020 North American Wife Carrying Championship at Sunday River in Newry. (Andree Kehn/Staff Photographer) Purchase this image

The annual North American Wife Carrying Championship at Sunday River isn’t an easy task for the participants, but you can cheer them on from the sidelines. Winning couples win the wife’s weight in beer, and five times her weight in cash. The 278-yard obstacle course will put teams to the test, and if you to dare participate, the fee is $40 per couple. Teams don’t have to be officially married couples, they just have to consist of one man and one woman, and both must be at least 21 years old. The event is part of Sunday River’s Fall Festival, which also includes the Blue Mountain Arts & Crafts Fair and New England Cornhole Championship.

10 a.m. -3 p.m. Oct. 12.  Sabbathday Lake Shaker Village, 707 Shaker Road, New Gloucester, free. maineshakers.com.

Tyler Credit, right, gives a tour of the herb gardens at Sabbathday Lake Shaker Village. ( Derek Davis/Staff Photographer) Purchase this image

The annual Harvest Festival at Sabbathday Lake Shaker Village offers live music, wagon rides, tours, traditional craft demonstrations, farm animals, lawn games and more. Sample herbs in the Shakers’ gardens, tour the barn with Brother Arnold and explore museum exhibits. Pick up fresh apples, local produce and seasonal house plants and grab food truck eats, cotton candy and popcorn. Cole Caswell will be on site creating tintype portraits.

Sam Adams Octoberfest at the Maine Lobster Chef Celebration during Harvest on the Harbor. (Brianna Soukup/Staff Photographer)

Oct. 15-17. Maine Studio Works, 170 Anderson St., Portland. harvestontheharbor.com.

Tantalize your taste buds during Harvest on the Harbor’s three signature events. On Oct. 15, quench your thirst with the Maine Distillers’ Guild Happy Hour. You’ll enjoy Maine-made gins, vodkas, bourbons, rums and more, along with some tasty snacks. The Oct. 16 Maine Lobster Chef of the Year Competition is as delicious as it sounds, with guests trying lobster dishes made by multiple chefs. The festival winds down on Oct. 17 with two Maine OysterFest sessions during which you can try plenty of fresh bivalves.

Oct. 16-18. L.L. Bean campus, Freeport, free, donations appreciated. campsunshinepumpkinfestivals.org.

Thousands of lit jack-o-lanterns are part of the annual Camp Sunshine Pumpkin Festival in Freeport. (Photo courtesy of Camp Sunshine)

The L.L. Bean campus will be overtaken with thousands of jack-o-lanterns during the annual Camp Sunshine Pumpkin Festival. On Friday, catch an outdoor screening of “Hocus Pocus.” Saturday features a variety of family-friendly activities, pumpkin carving and live music. On Sunday, you can break a sweat by participating in the Flannel 5K & Fun Run. The entire schedule will be available at campsunshinepumpkinfestivals.org. All funds raised go towards Camp Sunshine’s mission to provide hope, joy and community through experiences for children with life-threatening illnesses and their families.

9 a.m.-4 p.m. Oct. 17. Short Sands Beach, York. yorkharvestfest.com.

York’s 41st annual Harvestfest & Kidsfest brings a day of music, food, crafts and fall fun to Short Sands Beach. Music includes performances by Freight Train, Dan Blakeslee and his spooky alter ego, Dr. Gasp. KidsFest features games, crafts, face painting, demonstrations and activities. Shop the juried craft market featuring New England makers, browse vintage treasures and local goods at the Old Fashioned Market, and nosh on steak tips, lobster rolls, tacos, doughnuts and more.

Oct. 23-25. Downtown Ogunquit and surrounding areas. ogunquit.org/ogunquitfest.

Ogunquitfest is a three-day celebration of autumn that’s been happening for more than 20 years. The schedule includes a wide range of events and activities including a classic car show, Dogtoberfest costume parade, the Frannie Peabody High Heel Dash, artisan craft fair with more than 60 vendors and an array of food trucks. Attendees will also be treated to live music at the Dunaway Center and Dorothea Jacobs Grant Common.