The Maine Outsider is a free newsletter curating outdoor events across the state. Our mission is simple — help you find the fun and help great organizations find you.
Invite 140 // Sep 30The sun set behind Borestone Mountain, reflecting pink off the cloud edge of an approaching nor'easter. My wife sat in her kayak, paddle across her lap, as I took a photo, then another, then another, in disbelief. I’d like to say I planned for this moment, but of course I didn’t. Just an hour before, as the sky started to cloud over and the wind picked up, we debated whether strapping kayaks to the roof and driving down the bumpy road would be worth it at all. Maybe it was instinct or compulsive restlessness, but we went anyway. We embarked with modest expectations and returned in awe. The mountains were more dramatic, the lake was glassier, the pinks were pinker. Delight bloomed in the gap between what we expected and what we got. Dream big, summit peaks, chase the perfect shot, sure. But if you find that isn't working, try the opposite: expect less, and go anyway. ✌️ Max Reach 1,000+ Maine outdoor enthusiasts while supporting a community resource. View sponsorship opportunities.
Damariscotta River Clean-upThu, Oct 1 | Damariscotta | Free Clean up the Damariscotta River shoreline with local oyster growers, with boat transport to different sections of the estuary and trash bags provided.
Outdoor Film NightFri, Oct 2 | Portland | Donation Based Watch short films under the stars at Deering Center Pocket Park with a bring-your-own chair or blanket setup and suggested donation entry.
Hopkins Stream Fall PaddleSat, Oct 3 | Mount Vernon | Free Paddle Hopkins Stream through fall foliage to a wildlife conservation area with habitat for ducks and wading birds, with limited kayaks available to reserve.
Little Bigelow Mountain HikeSat, Oct 3 | null | Free Hike 6.2 miles up Little Bigelow Mountain with trained guides for views of the Bigelow Range and Flagstaff Lake, free and open to the public.
CELT Fall Cross Town WalkSat, Oct 3 | Cape Elizabeth | Paid Walk 8.6 miles across Cape Elizabeth from Portland Head Light to Kettle Cove, passing through marsh, woods, and pond ecosystems with carpools arranged.
Cider Press Stride + RideSat, Oct 3 | Bethel | Paid Run a 5K trail race or tackle an enduro mountain bike race through a community forest, with a cider press, scavenger hunt and bonfire on the side.
Summit Sisters: Group Trail RunMon, Oct 5 | Denmark | Free Run a technical 6-mile out-and-back up Pleasant Mountain's ridge with a supportive women-centered group that keeps everyone together and offers a halfway turnaround.
North American Wife Carrying ChampionshipSat, Oct 10 | Newry | Paid Carry your partner through a 278-yard obstacle course of log hurdles, sand traps, and a water hazard in a quirky race rooted in Finnish legend, with beer and cash for winners.
Maine Lobster RideSat, Oct 10 | Rockland | Paid Pedal 13, 30 or 50 miles of Midcoast roads and the St. George Peninsula, then celebrate at a finish-line festival with local food vendors.
Presumpscot River Revival RaceSat, Oct 17 | Windham | Paid Race canoes, kayaks, or paddleboards 2.5 miles on the Presumpscot River during fall foliage, celebrating 30 years of river restoration with food trucks. Coming Up (Previously Featured)Ride the Region | Fri, Oct 2 - Sun, Oct 4 | Paid Teens to Trails Outdoor Leadership Conference | Fri, Oct 2 | Paid Adventure Ready: Outdoor Skills Trainings for High Schoolers | Sat, Oct 3 | Paid Stars Over Katahdin | Sat, Oct 3 | Donation Based Queerly Camp | Fri, Oct 9 - Sun, Oct 11 | Paid Downeast Trail Festival | Sat, Oct 10 | Paid What did you think of this week's newsletter?Too many events? Wrong corner of Maine? Idea for something new? Your feedback goes straight into the next issue. Hey, I'm Max. I created the Maine Outsider to help people connect with organizations offering outdoor events and experiences around the state. I monitor 400+ newsletters, but I can't know everything. If you're hosting an event or have a tip about an upcoming experience, use our tip line to let me know. Thanks for reading. Now, get out there! |
The Maine Outsider is a free newsletter curating outdoor events across the state. Our mission is simple — help you find the fun and help great organizations find you.