October is one of our favorite times to explore Southern Maine. The summer crowds have thinned, the leaves are changing, and towns along the coast are trading beach days for pumpkins, craft fairs, costumes, comfort food, and classic New England fall festivals.
If you’re looking for an excuse to plan an October day trip or an entire fall weekend, York, Ogunquit, Kennebunk, and Wells all have big celebrations coming up. Here are a few Maine Faves to have on your radar this season.
York Harvestfest & Kidsfest – October 17
Saturday, October 17, 2026 | 9 AM–4 PM | York Beach
York knows how to do fall.
The 41st Annual Harvestfest & Kidsfest takes over the Short Sands Beach area on October 17 for a full day of food, shopping, music, and family activities. Organized by the York Region Chamber of Commerce, the festival has been a local tradition since 1986.
One of the highlights is the festival’s collection of juried crafters and Old-Fashioned Market vendors from across New England, making this a great opportunity to get a head start on holiday shopping while supporting artists, makers and small businesses. Come hungry, too: this year’s food lineup includes everything from steak tips and sausage subs to lobster, crab and tuna rolls.
There’s plenty of entertainment throughout the day. Freight Train is scheduled to bring its crowd-pleasing covers to the big tent, while longtime Harvestfest favorite Dan Blakeslee returns with folk music and storytelling, and his spooky alter ego, Dr. Gasp.
Families will want to make time for Kidsfest, where activities include crafts, face painting, games, and hands-on experiences. The current 2026 lineup even includes a make-and-take “bristlebots” STEM activity from Portsmouth Naval Shipyard outreach.
Admission is free, and complimentary festival parking is available at York’s Wild Kingdom. Organizers note that regular York Beach parking remains paid through the end of October.
Kennebunk HarvestFest – October 17
Saturday, October 17, 2026 | Downtown Kennebunk
If you’re closer to Kennebunk or want to make a full day of festival hopping, Kennebunk HarvestFest also takes place Saturday, October 17.
The Town of Kennebunk describes this year’s celebration as a day filled with family-friendly activities including games, live music, a parade, and more. The town is still adding details to the 2026 schedule, so it’s worth checking back as October gets closer.
Past HarvestFest celebrations give a pretty good idea of why this has become such a fun downtown tradition. Activities have spread across the Waterhouse Center and downtown Kennebunk, with pumpkins for kids, games, crafters, food, live music, a farmers market, activities at the Brick Store Museum, and a costume parade down Main Street.
It’s also a great opportunity to spend some extra time downtown. Grab breakfast or coffee before the festivities, explore the shops along Main Street, check out the activities, and then settle in for lunch or an afternoon drink.
And because the 2026 lineup is still developing, we’ll be watching for more announcements as the festival approaches.
OgunquitFest – October 23-25
Friday–Sunday, October 23–25, 2026 | Ogunquit
For a full weekend of fall fun by the ocean, it’s hard to beat OgunquitFest.
Now in its 23rd year, OgunquitFest combines Halloween fun, live entertainment, shopping, and some wonderfully quirky traditions into a three-day celebration spread throughout town.
There are plenty of signature events to look forward to. Kids can go trick-or-treating in downtown Ogunquit and Perkins Cove, while four-legged visitors get their turn in the spotlight during the Dogtoberfest costume parade. There’s also a classic car show at Main Beach, live music, food trucks, and a large artisan craft fair featuring more than 60 vendors.
Then there’s an OgunquitFest tradition that you won’t find at your average fall festival: Sunday’s High Heel Dash in Perkins Cove, which benefits the Frannie Peabody Center.
It’s also a particularly fun weekend to simply explore town. Walk Marginal Way with the fall colors as a backdrop, visit Perkins Cove, browse the shops and galleries, grab lunch at a favorite restaurant, and see what Halloween surprises you encounter along the way.
Best of all, admission to OgunquitFest is free.
Wells Family Jamboree – October 17
Saturday, October 17, 2026 | 11 AM–3 PM | Wells Harbor Park
Wells is getting in on the October fun with the 17th Annual Family Jamboree, a free afternoon of family-friendly activities at beautiful Wells Harbor Park.
Sponsored by the Wells Chamber of Commerce, the Family Jamboree takes place from 11 a.m. to 3 p.m. and brings together games, crafts, food, vendors, and more for a fun fall day by the harbor.
It’s an especially easy event to add to your family’s fall calendar. Admission is completely free, and the setting at Wells Harbor Park gives you plenty of room to enjoy the festivities while spending an October afternoon outside.
One thing to keep in mind: organizers say the Family Jamboree is a “shine only” event, so there won’t be a rain date if Mother Nature doesn’t cooperate.
Make October a Southern Maine Festival Month
One of the best things about fall in Southern Maine is that the season doesn’t end when the beach chairs get packed away.
October brings an entirely different energy to the coast. You can shop from New England makers at York Harvestfest, spend a classic fall day in downtown Kennebunk, take the family to Wells Jamboree, put your dog in a ridiculous costume for OgunquitFest, walk Marginal Way surrounded by autumn color, and finish the day with a cozy dinner at one of your favorite local restaurants.
York Harvestfest, Kennebunk HarvestFest, and Wells Family Jamboree all take place on October 17, followed by OgunquitFest October 23–25, giving you two weekends in a row to get out and enjoy fall in Southern Maine.
We’ll be keeping an eye on schedules and announcements as the events get closer, so stay tuned to Maine Faves for more fall events, things to do, and seasonal favorites throughout Vacationland.
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