There’s something to be said for the crunching sound of red and orange leaves beneath your feet. Autumn in Maine is particularly spectacular because the air feels cleaner, the foliage is among the best in the world, and we get to start wearing our favorite sweaters. Sometimes summer stretches way into fall and sometimes winter arrives much too early, but either way, we hope you have an autumn to remember, and are here to help with a smattering of fall offerings. Does it include pumpkins? Of course! But we also hit you with several other fun events and hope that as the days grow shorter, your smile grows wider.

A lively scene from 2018’s Oktoberfest at Sebago Brewing Co. Photo courtesy of Sebago Brewing Co.

Sebago Oktoberfest
2-7 p.m. Saturday, Sept. 21. Sebago Brewing Co., 616 Main St., Gorham, $45 includes stein, $35 bring-your-own stein, 21-plus.
Sebago’s Oktoberfest smacks of fall fun, and if you need to bust out your lederhosen for the occasion, we don’t blame you one bit. The Gorham brewery’s celebration features traditional Oktoberfest lagers (along with other Sebago beers and specialty Ice Pik vodka cocktails), a stein-holding contest, traditional German feast, best-dressed contest, cornhole, jumbo soft pretzels and live music from Tricky Britches and Hello Newman. We have a feeling that this Oktoberfest will be lager than life.

Harvest Festival at Pineland Farms. Photo courtesy of Pineland Farms, Inc.

Harvest Festival
10 a.m. to 2 p.m. Saturday, Sept. 28. Pineland Farms, 15 Farm View Drive, New Gloucester, $6 in advance, $7 day of event.
It’s a family affair at Pineland Farm’s Harvest Festival. If nothing else, who doesn’t love to make their way through a corn maze and tromp around a pumpkin patch? But you can do much more than that, including checking out an apple cider demonstration and listening to music from the Sea Grass Band. There’s also something called the farmer’s obstacle course, and we don’t think you, or your adventurous kids, should bale on this.

Apple Day Family Festival in Falmouth. Photo by Ariana van den Akker, Courtesy of Maine Audubon

Apple Day Family Festival
10 a.m. to 2 p.m. Saturday, Oct. 5. Maine Audubon at Gilsland Farm, 20 Gilsland Farm Road, Falmouth, $7, free for 2 and under.
This year marks the 32nd anniversary of the Apple Day Family Festival at lovely Gilsland Farm. Maine Audubon invites you and your family to spend part of the day in the great outdoors, and the schedule includes games, workshops, cider-making, face-painting, an apple toss, scavenger hunt and music by the Sea Slugs. Bring the entire family, including Granny Smith. They’re in for some hardcore fun.

Tom Lishness of Windsor and Russell Orms of Austin, Texas, costumed as a viking, compete in the powerboat division race of the Pumpkin Regatta, part of the Pumpkinfest in Damariscotta in 2017. Carl D. Walsh/Staff Photographer

Damariscotta Pumpkin Festival & Regatta
Saturday to Monday, Oct. 12 to 14. Downtown locations, Damariscotta.
Oh my gourd, they sure do love their pumpkins in Damariscotta, and the annual Pumpkin Festival is a three-day pumpkin party. Carve out some time for these festivities, which include a pumpkin dessert contest, pumpkin pie eating contest, pumpkin pancake breakfast, giant pumpkin parade, pumpkin derby (small, non-motorized pumpkin races), giant pumpkin catapult and pumpkin slingshot, kids’ pumpkin hunt, giant pumpkin drop and the pumpkin piece de resistance – the Pumpkinboat Regatta. Lest there be any doubt, it is indeed a boat race on the Damariscotta River among boats made out of pumpkins. Get pumped!

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1-5 p.m. Saturday, Oct. 12. Mutty Paws Academy, 411 Payne Road, Scarborough, $20 in advance, $25 day of event.
The dog days of summer are long over, but if your pooch has been hounding you to have some fun, then put a paw print on Oct. 12. Barktoberfest is held outside at Mutty Paws Academy, and the fun includes raffles, a dog costume contest, games, a bonfire, food and live tunes from The Middle Men. For an additional $10, anyone 21 or older can hit the beer tent to enjoy unlimited 4-ounce pours from Funky Bow Brewery. You can also learn all about the wonderful work done by Fetching Hope Rescue, which saves neglected, abused and stray dogs. As for your loyal companions, if they’re leashed and social, they’re more than welcome to join the party. Don’t stop retrievin’! P.S. Nobody likes wet fur, so the rain date is on Sunday, Oct. 13.


Sloth Astronaut/

Levitate Flannel Jam
3-9 p.m. Sunday, Oct. 13. Maine Craft Distilling, 123 Washington Ave., Portland, $39 in advance, $49 day of festival, $10 kids.
The name alone gives us all the fall feels! Flannel Jam is a fall-themed celebration featuring a hot spiked cider cocktail lounge, specially crafted local brews, food trucks, hot cider doughnuts and a kids’ hay maze and corn pool (picture a kiddie pool filled with corn kernels) along with a powerhouse lineup of live music. Headlining the day is bluegrass/folk/rock act Trampled By Turtles. You’ll also hear sets from The Ballroom Thieves, Liz Cooper & The Stampede, Jason Spooner Band and Town Meeting. In other words, you can count on one hand how many sensational bands are playing at this thing while you root around your closet, pulling out everything flannel that you own.


Culinary creations abound at Harvest on the Harbor. Photo courtesy of Harvest on the Harbor

Harvest on the Harbor
Thursday, Oct. 17, to Sunday, Oct. 20. Brick South, Thompson’s Point, Portland.
You don’t have to be a hardcore foodie to get your fill at this event. Since 2007, Harvest on the Harbor has been a celebration of the wealth of award-winning local and independently owned restaurants, breweries and distilleries in Portland and beyond. Most events take place under one roof at Thompson’s Point, and they include the Chef + Farmer Harvest Dinner (a benefit for Full Plates Full Potential), Maine Lobster Chef of the Year 10-course lobster luncheon, Straight Up Maine Distillers Boozy Bash, Bloody Mary Pig Roast Brunch, Maine Oysterfest with the Maine Oyster Co., VIP Market Brunch and the daily Culinary Market on the Harbor. Want more? There’s also the Fusion Coffee Lab with Coffee By Design at its Diamond Street location. To sum it all up in five concise words: Eat, drink and be merry!

Camp Sunshine Pumpkin Festival in Freeport Photo courtesy of Camp Sunshine

Camp Sunshine Pumpkin Festival
Friday, Oct. 18, & Saturday, Oct. 19. Downtown Freeport.
You can’t have a proper fall without, at some point, being surrounded by a massive amount of pumpkins. That said, you really autumn know about the annual Camp Sunshine Pumpkin Festival. The streets of downtown Freeport and area around L.L. Bean become a pumpkin wonderland as nearly 10,000 jack-o-lanterns are lit at the strike of 5 p.m. The festival also features public pumpkin carving, treats from the Cauldron Cafe, festival gear shopping at the Boo-tique, Mad Science of Maine, a costume parade with Miss Maine and music from DJ Nate Hicks, OC & The Offbeats and Roxy by Proxy.

Sugarloaf’s base lodge patio is a prime party spot. Photo courtesy of Sugarloaf

Maine Beer Box International Beer Festival
Noon to 4 p.m. Saturday, Oct. 26. Sugarloaf Mountain, Main Street, Carrabassett Valley, $37.50, 21-plus.
Does the idea of enjoying unlimited beer samples out of a souvenir drinking glass in an idyllic setting sound like a fabulous idea? If so, follow this four-word piece of advice: Head to the ‘Loaf! The Maine Beer Box International Festival, with the world’s biggest kegerator – the Maine Beer Box – is happening, and it’s a great way to party on the mountain before ski season starts. The Maine Beer Box has an epic 78 taps, and they’ll all be flowing, with beers from around Atlantic Canada, most of which have never been poured in the U.S., along with plenty of Maine brews. Additionally, several Maine breweries will have pop-up tents all around the lodge’s patio, creating a true beertopia, which will likely be further enhanced by a colorful foliage situation.

You never know what’s going to roll by you during the Rolling Slumber Bed Races in downtown Brunswick. Gordon Chibroski/Staff Photographer

Rolling Slumber Bed Races
11 a.m. Saturday, Nov. 9. Park Row, downtown Brunswick, free for spectators, $35 entry, $25 if received by Oct. 31.
They sure know how to have fun in Brunswick, and one particularly grand example of this is the annual Rolling Slumber Bed Races. It’s one of the most original ways there is to foster community, and it’s been happening for nine years. Area families, businesses and local organizations create funny yet functional beds, all with a special feature: They’re on wheels and will race each other for prizes in speed, creativity and team spirit. Spectators – including you – line the streets downtown and revel in what’s always the best kind of bedlam.

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