Maine Events in September 2026
More dates are rolling in for Maine events in September. 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 September in Maine, and I hope to see you at some of these Maine fall events!
Maine Events in September 2026
- August 29- Sept 7 Windsor Fair, Windsor
- 3-6 4×4 Proving Grounds, Lebanon – The Maine Event
- 3-7 Blue Hill Fair, 233 Ellsworth Rd, Blue Hill
- 4-7 Harmony Free Fair, 1 Fairway Lane, Harmony
- 5 Cruzin for our Kids: Enfield School Ride, ATV ride, Cold Stream Cruzers, 105 Old County Rd N, West Enfield
- 6 Pine Brook Mudders, Steuben
- 10-12 Litchfield Fair, 44 Plains Rd., Litchfield
- 10-13 Clinton Lions Agricultural Fair, 1450 Bangor Road, Clinton
- 10-13 52nd International Seaplane Fly-In, Moosehead Lake, Greenville
- 11-13 Eastport Pirate Festival
- Pirate ship sails into port, entertainment, activities, food, games, bed races, & more!
- 11-13 Trails End Festival, Millinocket
- Free live music, food, fun, & more!
- 12 Maine Open Lighthouse Day, Around 17 lighthouses are open to the public, see website for details
- 12 Bar Harbor Half Marathon & 5k, 21 Park St, Bar Harbor
- 12 The NewEngland Parkinson’s Ride, 7 Ball Park Way, Old Orchard Beach
- 12 Stayin Alive; Cruzin for Suicide Prevention, ATV ride, Cold Stream Cruzers, 105 Old County Rd N, West Enfield
- 12 Maine Lighthouse Ride bike ride
- 2 Fort Rd, South Portland
- 12 Skowhegan River Days
- 12-13 Spud Speedway Mega Marketplace, Caribou
- Yard sale, flea market, swap shop, crafts, antiques, auto
- Stock car races, ATV drags & mud runs
- 13 The Maine Cheese Festival, Manson Park, Pittsfield
- 16-19 Oxford Fair, 67 Pottle Road, Oxford
- 18-20 Dustbowl, Spud Speedway, Caribou
- Demo derby, snowmobile grass drags, stock car racing, & more
- 18-20 New Portland Lions Fair, 280 School St., North New Portland
- 19 Dempsey Challenge presented by Hearts of Pine cycling event, 46 Beech St, Lewiston
- 19 28th Annual Bethel Harvestfest
- 20 The Great Lincoln Marathon & Half, 10 Prince St, Lincoln
- 20-26 Farmington Fair, 292 High St., Farmington
- 25-27 Common Ground Country Fair, 294 Crosby Brook Rd, Unity
- 26 22nd Annual Maine Lakes Brewfest, 40 Brag Way, Bridgton
- Live music, food, & beer
- 26 Apple Pumpkin Festival, Livermore Falls
- 26 Portland Oktoberfest, Mathew’s, 133 Free St, Portland
- Beer, food, music, & fun
- 26-27 Pemaquid Oyster Festival, Mine Oyster Restaurant, Boothbay Harbor
- 27-October 3 Cumberland Fair, 196 Blanchard Rd., Cumberland Center
- 28-October 5 Fryeburg Fair, 1154 Main St., Fryeburg
- TBD Ebb Tide Marathon: FW 11 Miles paddle race, Penobscot River, Brewer waterfront boat launch to South Orrington Mill Creek boat launch
- TBD Meadow Brook Mudders, New Portland Fair Grounds- Nighttime Mud Run at the Fair
- TBD Champion for the Cure Challenge paddle event/fundraiser, Penobscot River, Brewer
- A ‘fun’ paddle event to raise donations for cancer care and research
- Courses of varying length to suit all participants
- TBD Northwoods Truck Pull & Mud Run, Avon
- TBD Cathance River Race, THE NEW Paddle Craft Only Boat Launch off of Route 24 in Bowdoinham