Pumpkin spice debates aside, autumn sure is a sublime time to be in Maine. From crisp afternoons to spectacular foliage and the calm before holiday madness, it’s a season to behold. So start thinking about locating that stash of sweaters and marking up your calendar, because we’ve got some fabulous fall events to choose from.

Ricker Hill Orchards in Turner. Russ Dillingham/Sun Journal

Maine Apple Sunday
Sunday. Statewide. maineapples.org
The Maine State Pomological Society is thrilled to the core to present the 22nd annual Maine Apple Sunday. Several apple orchards and farms all over the state are participating, and the day marks what’s considered to be the peak of the season, as summer apples are still around while the other crops are ready to be picked. A number of orchards will offer special activities and free samples. So make a plan to get off your McIntush and hit an orchard or two.

A scene from Krystal Puppeteers’ “Tears By The River.” Photo courtesy of Mayo Street Arts

Puppets in Portland Festival
Sept. 20-25. Portland locations. puppetsinportland.org
Mayo Street Arts is going all out this year when it comes to puppets. Puppets in Portland happens over the course of six days and it’s an international festival of puppetry arts. PiP includes more than a dozen professional puppeteers, technicians and sound engineers, representing 10 countries, who are all enthusiastic about sharing their love for the diverse world of puppets. Guest artists include Kenyan/German Krystal Puppetters, Dafa Puppet Theatre out of Prague, and Brooklyn, New York’s Lone Wolf Tribe. It all begins at 6 p.m. on Sept. 20 with the PipPip parade through East Bayside to Mayo Street Arts, followed by a PiP festival prelude party. Performances and workshops happen at Mayo Street Arts, First Parish Unitarian Universalist Church and Children’s Museum & Theatre of Maine.

Freeport Fall Festival
Sept. 30 through Oct. 2. Downtown Freeport. freeportfallfestival.com
The 23rd annual Freeport Fall Festival is a wonderful way to experience – and shop from – more than 175 Maine artists and craftsmen, along with some talented food producers who shine with things like jams, breads, fresh produce and oysters. The festival also includes three days of live music in L.L. Bean’s Discovery Park, and a partial list of performers includes The Old Blues Kats, An Overnight Low, The High Road and String Tide. Along with Discovery Park, locations for the festivities include the Key Bank lawn, Freeport Village Station courtyard and the corner of West and Main streets. Kids’ activities include a bubble tent, make-and-take crafts, glitter tattoos and face painting.

Maine Craft Weekend
Oct. 1 and 2. Statewide. mainecraftweekend.org
The 10th annual Maine Craft Weekend is statewide celebration that includes open studios, workshop tours, demonstrations, classes, craft beer collaborations, pop-up shops, craft gallery openings, exhibitions and much more. At present, seven cities are involved, so you can take your pick from Bath, Biddeford, Bucksport, Ellsworth, Freeport, Gardiner and Monson. Keep an eye on the website for updates on specific happenings at each of the locales.

A painted pumpkin created at the 2010 Pumpkinfest in Damariscotta. Derek Davis/Staff Photographer

Damariscotta Pumpkinfest & Regatta
Oct. 7-9 Main Street Damariscotta and Newcastle. mainepumpkinfest.com
If you love giant pumpkins paired with family-friendly fun, be sure to head to Damariscotta for their annual Pumpkinfest and Regatta. Gigantic painted pumpkins will be on display all around town, and you can watch the artists create their magic. You’ll also enjoy street performers doing their thing. There’s a big parade on Main Street, and on the final day, the harbor will be the place to be as boats carved out of enormous pumpkins will be deployed by creative and brave captains.


Fall Foliage Festival
10 a.m. to 5 p.m. Oct. 8, 10 a.m. to 4 p.m. Oct. 9. Boothbay Railway Village, 586 Wiscasset Road, Boothbay, $5, free for 12 and under, $5 for train rides. railwayvillage.org
The Fall Foliage Festival has been happening for more than five decades and, heck, even the drive to it could be festooned with fabulous foliage. Upon arrival at Boothbay Railway Village, you’ll find all sorts of vendor booths, entertainment, live music and local food. While you’re there, be sure to explore the four acres that are home to the antique car museum with more than 60 cars. You’ll also get to visit with the village goats. Best of all, you can ride an authentic steam locomotive. All aboard for quintessential fall fun!

Water Street was full of booths and people during Swine and Stein festivities on Oct. 9, 2021, in downtown Gardiner. Joe Phelan/Kennebec Journal

Swine & Stein Brewfest
Noon to 5 p.m. Oct. 8. Water Street, downtown Gardiner, $40, $50 VIP early entrance, $10 non-drinker ticket. swineandsteinbrewfest.com
Your thirst sure will be quenched on Water Street during the annual Swine & Stein Brewfest. Here, you’ll sip samples in an open-air beer garden from several local breweries and distilleries, including Bath Ale Works, Black Pug Brewing, Freedom’s Edge Cider, Run Amok Mead and Outland Farm Brewery. Swine & Stein Oktoberest will also keep your belly sated with several food trucks and local restaurants, including pig roast hosts The Blind Pig Tavern. The day also features live music, giant Jenga and a beer and moustache competition.

Fall Festival
Oct. 8 and 9. Sunday River, 15 South Ridge Road, Newry. sundayriver.com/events/fall-festival
Sunday River’s Fall Festival packs a whole bunch of autumnal amusement into one weekend. Events and activities include the 23rd annual North American Wife Carrying Championship, Blue Mountain Arts & Crafts Fair, New England Corn Hole Championships, Sunday River Sports annual fall sale, live music and scenic chondola rides. Day trip it or make a weekend of it by staying right on the mountain. Check the Sunday River site for rates and availability.

Flannel shirts are optional at the Flannel Jam music festival in Portland. Daniel Rossi Limpi/Shutterstock.com

Flannel Jam
2 p.m. Oct. 9. Maine Craft Distilling, 123 Washington Ave., Portland, $59, $15 for 4-12 years old. levitateflanneljam.com
The annual Levitate Flannel Jam is a big, outdoor music festival happening at Maine Craft Distilling that’s stacked with great music, food and activities. On the music front, you’ll hear sets by Greensky Bluegrass, Molly Tuttle & Golden Highway, Midnight North, The Whiskey Treaty Roadshow, King Kyote, Aldous Collins & The Like Minded Folk, Buckle & Shake, Blacktop Strut and Silver Heels. You’ll also enjoy hot spiked cider, warm cider doughnuts, art and handmade goods, and a kids’ corral. Plenty of food trucks will also be on site to keep you well fed. You don’t need to wear flannel to attend, but why wouldn’t you?

Camp Sunshine Pumpkin Festival
Oct. 21 & 22. L.L. Bean Flagship campus, 95 Main St., Freeport. campsunshinepumpkinfestivals.org
It’s all about the pumpkins all weekend long in Freeport during the annual Camp Sunshine Pumpkin Festival. Details are still being finalized, but past celebrations have included live music, treats, kids’ games, a costume parade and, of course, carved pumpkins as far as the eye can see. All proceeds will benefit Camp Sunshine, an award-winning retreat for children with life-threatening illnesses and their families. For $10, you can go online now to sponsor a Glow Heart pumpkin in honor or memory of a loved one that will be displayed during the festival. Check back in a few weeks for the complete schedule.

Harvest on the Harbor welcome banner. Photo by Kristie West

Harvest on the Harbor
Oct. 27-29. O’Maine Studios, 54 Danforth St., Portland. harvestontheharbor.com
It’s the most wonderful weekend of the year, if you’re a foodie, because Harvest on the Harbor features some seriously mouth-watering events. Celebrate Maine’s favorite crustacean at The Maine Lobster Chef of the Year competition, during which you’ll chat with the chefs while tasting their entries. Meet Your Maker features locally-made Maine Distillers Guild spots, and you’ll enjoy cocktail and food pairings. The Maine Oyster Fest is one shell of a party with all sorts of oysters, drinks and live music. Want to slay at this year’s Halloween parties? Register for the Zombie class happening at Three of String Spirits. A cheese and wine pairing event is also in the works, so keep an eye on the event site for details.

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