Second-Half-of-Summer Event Grab Bag

Check out these fun, second-half-of-summer and early fall events from across Maine.

Whether your idea of an ideal outdoor event is checking out the unparalleled night skies above Katahdin Woods and Waters National Monument or grinding 100 kilometers on your bike, this grab bag of events scheduled for late summer and fall should give you some ideas on how to get the most out of Maine’s summer. Bonus: most of these events support some cause, making your registration fees do double duty – fun for you and much needed funding for groups that need it. No, this list isn’t complete and it probably left out some great events that we didn’t catch. And yes, September counts as summer here at The Maine Outpost.

Maine Outdoor Film Flagship Festival – July 21-26 – Portland (various venues)

This annual event brings some of the best outdoor films to Portland Maine for a week of community and cinema. Check out the full schedule and snag tickets here.

West Forks Riverfest – August 8-9 – West Forks Maine

Now in its fourth year, the West Forks Riverfest is a celebration of Maine’s whitewater paddling community in the heart of Maine’s whitewater paddling community. With music, food, speakers, and big releases on the Kennebec and Dead River both Saturday and Sunday, it promises big waves and big fun.

American Packrafting Association Eastern Roundup – September 4-7 – Big Eddy Campground – (near) Millinocket

Link up with fellow packrafters in this regional American Packrafting Association event, held this year in Maine. Camp at Big Eddy Campground and paddle tiny, awesome boats down the Lower West Branch of the Penobscot, Seboomook section of the Penobscot, South Branch of the Penobscot and more!

Mainely Gravel Race – August 8 – Pineland Farms – New Gloucester

One of Maine’s premier gravel cycling races takes place August 8th on Pineland Farm’s buffed out cross country ski trails. Ride for run or ride to win with two courses – a 35-mile short course and a 58-mile long course. $5 from every registration is donated to the Independence Association – a group that helps people with disabilities obtain full and independent living throughout Midcoast Maine.

Woods and Waters Day – August 15 – New England Outdoor Center – Millinocket

Join Friends of Katahdin Woods and Waters for their annual Woods and Waters Day on August 15th. This year marks the 10th anniversary of Katahdin Woods and Water National Monument, so it’s a great year head up to NEOC and enjoy the farm-to-table buffet, Maine Beer Co beer, live music, dancing, and more. Tickets are $50 and support Friends of Katahdin Woods and Waters.

Northwoods Gravel Grind –  September 12 – Rangeley

Ever notice the crazy amount of gravel roads up around Rangeley? Well, here’s your chance to explore more than 35 miles of them with stocked aid stations, clear route markers, and a host of gravel pals. In the past, they’ve given cash prizes if you snap a photo of a moose along the race route, so keep your eyes peeled!

AMC’s Summer Gravel Weekend – July 31-August 2 – Medawisla Lodge and Cabins – (near) Greenville 

Back in 2024, AMC started promoting the epic gravel riding on it’s more than 100,000 acres of land in the 100-Mile-Wilderness area of the North Woods. With cozy cabins and an off-grid-but-modern lodge, Medawisla Lodge and Cabins (one of AMC’s three complexes in the area) delivers the right kind of roughing it after a day of grinding logging roads…post-ride sauna, anyone?

AMC’s Equinox Gravel Weekend – September 18-20 – Medawisla Lodge – (near Greenville)

Join AMC and friends for another gravel riding weekend in late summer and celebrate the Equinox. Skills workshops, tasty food, campfires under the stars, it all adds up to a great weekend.

Maine Woods Rambler – September 25-27 – Medawisla Lodge and Cabins (near Greenville)

This weekend gravel-riding extravaganza is put on by the Bicycle Coalition of Maine and AMC and is anchored by Saturday’s (9/26) rides, which include four distances: 19 mi, 32 mi, 55 mi, and 79 mi. Packraft Maine will be there Friday and Sunday to take folks on a bikerafting adventure (though the Friday bikerafting is already sold out). If you’re gravel biking curious or a seasoned gravel grinder, this is a great event in a beautiful setting.

AMC’s Mountain Biking Weekend – October 2-4 – Gorman Chairback Lodge and Cabins – (near) Greenville

Gravel riding not your thing, but still want to check out AMC’s riding opportunities? They got you covered. Pedal trails and gravel roads during this mountain-biking focused weekend at the Gorman Chairback Lodge and Cabins, one of AMC’s restored sporting camps just east of Greenville.

Blue Hill Mountain Trail Fest – August 1 – Blue Hill Maine

This annual event brings runners from all over to celebrate Blue Hill, known as “Awanadjo” by the Penobscots, which means “small, misty mountain.” Fittingly all proceeds from the 5K, 10k, 25k and 50k trail runs are donated to the Wabanaki Alliance.

Stars Over Katahdin – October 3 – Taylor’s Katahdin View Campground – Stacyville

Join Friends of Katahdin Woods and Waters at Taylor’s Katahdin View Campground, located in Stacyville, on the southern entrance to KAWW National Monument, for this annual celebration of all things celestial. In case you didn’t know, KAWW is a designated International Dark Sky Sanctuary, and crisp fall nights make for a perfect time to view some of the darkest skies east of the Mississippi. Bonus: there will be some high-tech telescopes available to participants, so you’ll be able to see more than just a sky filled with enough stars to make you feel reeeaaalllyyy small. A food truck will be selling food and drinks if you don’t bring your own. No dogs at this event (except service animals).

Megunticook Trail Festival – September 12 – Camden

Take advantage of this unique opportunity to race in Camden Hills State Park and benefit Niweskok, a Wabanaki-led organization that strengthens food sovereignty, healing, and community connections in the Penobscot Bay region, with a donation option at registration. With three different races – the Wicked Tough 10k (boasting 1,600 feet of vert), the Halffast 20k (mellower than the 10k, it lopes along a gravel trail), and the Megunticook 50k (a bruiser that takes in 90% of the park’s trails) – every runner can find something that’s their speed.

Loon Echo Race Series – July 26, August 30, September 12 – Bridgton

This trail race series supports the Loon Echo Land Trust, a Bridgton-based nonprofit organization that works to conserve land, protect public access to the outdoors, and build and maintain trails in the Lakes Region.

The Crooked River 5k is a beginner-friendly race in Harrison on July 26.

The Bald Pate 10k and Five Fields 50k take off on August 30 and offer challenging runs for those looking for a technical course (the 10k) or those looking for a longer distance (the 50k).

The last race of the season is the Pleasant Mountain Race, a half-marathon-length race that traverses Pleasant Mountain, held on September 27.

TUCARD – September 12 – Near Bangor

TUCARD stands for the Terrifically (and Unnecessarily) Complicated Adventure Race and Duathalon. This wild race requires competitors (individual or teams) to hit several waypoints using two forms of human-powered locomotion (eg: canoe and feet, bike and swim). While the starting and finishing area are released now, the on-course waypoints aren’t released until you register, and a last-minute waypoint involving a sparkly unicorn is released the day of the event, throwing any pre-race planning into question. The race is organized by the Marsh Island Trail Runners, a fun-loving group of trail runners in the Bangor area. While the rules, the FAQ, and the race description, suggest this is one of the wildest, most fun, real-deal adventure races in Maine, the ethos behind it – celebrating and supporting Maine’s unparalleled private land access – is serious and well worth supporting.