Maine Events in October 2026
More dates are rolling in for Maine events in October. Check back often as I update the list! Visit my online Maine Outdoor Events Google Calendar here for more information about each event and a complete list of all events for the year, or click the event’s title to go directly to their website.
Have a fantastic October in Maine, and I hope to see you at some of these Maine fall events!
Maine Events in October 2026
- September 27- 3 Cumberland Fair, 196 Blanchard Rd., Cumberland Center
- September 28- 5 Fryeburg Fair, 1154 Main St., Fryeburg
- 2-4 Barnyard All Terrain, Livermore- Halloween Mud Bash
- 2-4 27th Annual Freeport Fall Festival
- 3 The County’s Fall Festival to End Hunger, 37 Graves Rd, Mars Hill
- Live music, food trucks, beer garden, chairlift rides, bonfire, golf scramble, & ATV ride-in
- 3 Ride with Ryleigh: Down Syndrome Ride, ATV benefit ride, Cold Stream Cruzers, 105 Old County Rd N, West Enfield
- 3 Chili, Chowder, & BrewFest, Bath Freight Shed, 27 Commercial St, Bath
- 3-4 Full Throttle ATV Fair, Spud Speedway, Caribou
- ATV/SxS pulls, mud runs, grass drags, & stock car racing
- 4 Pine Brook Mudders Mud Runs, Steuben
- 4 Ride for a Cure- Downeast Region, ATV benefit ride, Acadia Area ATV’ers, Hancock
- 4 Maine Community Bank Marathon, Half Marathon, and Relay, 55 Baxter Blvd, Portland
- 4 Cadillac Challenge cycling race, 21 Park St, Bar Harbor
- 10 Swine & Stein Brewfest, Water St, Gardiner
- Live bands, food trucks, beer, wine, & more
- 10-11 58th Annual Fall Foliage Festival, Boothbay Railway Village
- 10-11 Sunday River Fall Festival, Sunday River Ski Resort, Newry
- Scenic chondola rides, food, music, arts & crafts, North American Wife Carrying Championship, New England Cornhole Championship, & more!
- 10-11- Maine Maple Fall Fest Weekend, various sugar houses across the state
- 10-12 Damariscotta Pumpkinfest & Regatta, Damariscotta
- Decorated Atlantic Giant pumpkin display downtown, road race, parade, pumpkin boat race (people paddling in the ocean in giant, caved out pumpkins), food, games, entertainment, & more!
- 17 41st Annual Harvestfest & Kidsfest, Short Sands Beach, York Beach
- 17 Ride for a Cure- Central Region, ATV benefit ride, Topsham Fairgrounds, Topsham
- 17 Spud Speedway Halloween Howler, Caribou
- Stock car racing, 100-lap street stock race, awards party, trunk-or-treat
- 17 5k for Heating Oil supporting the Maine Veterans Project, 100 Washington St, Brewer
- 10-11- Maine Maple Fall Fest Weekend, various sugar houses across the state
- 18 Great Maine Apple Day, MOFGA, Unity
- 18 Mount Desert Island Marathon, Half, & Relay, Bar Harbor
- 23-25 22nd Annual OgunquitFest, Ogunquit
- 24 Haunted Trail & Pumpkin Scavenger Hunt, ATV ride, Cold Stream Cruzers, 105 Old County Rd N, West Enfield
- 25 Moosehorn Ghost Run Half Marathon & Relay, 103 Headquarters Rd, Baileyville
- 29-30 Harvest on the Harbor, 170 Anderson St, Portland
- 31 Maine OysterFest, 170 Anderson St, Portland
- TBD Muskrat Scramble paddle race, East Orrington
- TBD Fon Solo Gravel/Last Standing/Cider Cross (Maine Gravel Series), Alna
- TBD Flatwater Paddle Race, Long Pond, Somesville