Tue, Sep 1, 2026

Loon Echo Land Trust’s 2026 Trek for the Trails

Loon Echo Land Trust trails and anywhere you explore · Maine Lakes Region

Support the trails you love during Loon Echo Land Trust’s free, two-month outdoor challenge. Participants can log miles by walking, hiking, running, biking, paddling, or rolling anywhere they…

Sun, Oct 4, 2026 at 9:00 am

Mill Brook Traverse Hike at Mill Brook Preserve

Mill Brook Preserve — Northern Trailhead · Westbrook

Join Presumpscot Regional Land Trust volunteer and certified Appalachian Mountain Club trip leader Natalie Skovran for a fall-foliage hike through Mill Brook Preserve. This moderate but rugged hike…

Sun, Oct 4, 2026 at 4:30 pm

Fall Foliage Cruise aboard the Songo River Queen II

Songo River Queen II · Naples, Maine

Enjoy autumn color on Long Lake during this special adults-only Fall Foliage Cruise aboard the Songo River Queen II. The two-hour community fundraiser features live music by Thomas…

Tue, Oct 6, 2026 at 1:00 pm

Edes Falls Park Dedication Day

Edes Falls Park · Naples

Celebrate the completion of the Edes Falls Dam removal project and the formal recognition of Edes Falls Park in Naples.The project restored fish passage along the Crooked River,…

Fri, Oct 9, 2026 at 6:30 pm

Annual Halloween Fundraising Investigation at the Old Red Church

Old Red Church · Standish, Maine

Take part in the annual Halloween fundraising investigation at the historic Old Red Church and nearby Standish Cemetery. Presented by Pine State Paranormal and community partners, the evening…

Sat, Oct 10, 2026 at 10:00 am

Windham Historical Society’s Fourth Annual Fall Harvest Festival

Windham Historical Society Village Green · Windham

Celebrate fall at the Windham Historical Society’s fourth annual community festival on the Village Green.The day will feature contests, tours of the historic buildings, live musical entertainment, a…

Sat, Oct 10, 2026 at 1:30 pm

Trunk or Treat & Frye’t Fest 2026

Frye Island Community Center · Frye Island

Celebrate the end of the season on Frye Island with a family-friendly Trunk or Treat and Frye’t Fest at the Frye Island Community Center.The Town of Frye Island…

Sat, Oct 10, 2026 at 3:00 pm

The Naples, Maine Rocktoberfest & Nightmarket

Naples Causeway · Naples, Maine

Rocktoberfest and the Nightmarket return to the Naples Causeway for an autumn celebration presented by Town of Naples, Maine Events & Experiences. Enjoy live music and a festive…

Sun, Oct 11, 2026 at 10:00 am

Chickadee Quilters 45th Annual Quilt Show

Stevens Brook Elementary School · Bridgton, Maine

Chickadee Quilters presents its 45th annual quilt show, “We the Quilters: Honoring America’s 250th in Fabric & Thread.” The two-day show features a quilt exhibit, children’s quilt exhibit,…

Fri, Oct 16, 2026 at 9:00 am

Saint Joseph’s College of Maine Homecoming 2026

Saint Joseph’s College of Maine · Standish, Maine

Saint Joseph’s College of Maine welcomes alumni, current parents, online learners, Monkstoberfest fans, friends of SJC, and the wider community to a full Homecoming weekend on its Sebago…

Sat, Oct 17, 2026 at 8:00 am

Operation Ray of Light Fall Family Festival and Vendor Fair

Operation Ray of Light at Watchic Lake · Standish, Maine

Operation Ray of Light presents its first annual Fall Family Festival and Vendor Fair at Watchic Lake. The community celebration will feature more than 50 vendors, family activities,…

Sat, Oct 17, 2026 at 9:00 am

Windham Community Forest Celebration

Windham Community Forest — Atherton Hill Trailhead · Windham, Maine

Join us at Windham Community Forest as we officially open the new Universal Access Trail and celebrate the unveiling of a new name for the combined conservation lands…

Sat, Oct 17, 2026 at 10:00 am

Standish Public Safety Fair

Standish Municipal Center · Standish, Maine

Explore fire prevention, emergency services, and public safety at the Standish Public Safety Fair. Families can meet local first responders, see emergency vehicles up close, and learn practical…

Sat, Oct 17, 2026 at 10:30 am

Presumpscot River Revival Race 2026

Dundee Park · Windham, Maine

Celebrate the Presumpscot River’s comeback with a friendly paddle race, food, fall foliage, and family-friendly community activities at Dundee Park.The event features a 2.5-mile mass-start circuit for canoes,…

Sun, Oct 18, 2026 at 11:00 am

Little Duck 50K and 10K Trail Running Race

East Windham Conservation Area · Sebago Lakes Region

Sun, Oct 18, 2026 at 12:00 pm

2026 Camp Sunshine Pumpkin Festival

L.L.Bean Flagship Store · Freeport, Maine

Continue the Camp Sunshine Pumpkin Festival celebration with live music, delicious food offerings, family-friendly activities, and a relaxed Sunday atmosphere at the L.L.Bean Flagship Store in Freeport. The…

Sun, Oct 18, 2026 at 3:30 pm

PRLT Annual Meeting at Randall Orchards

Randall Orchards · Standish, Maine

Celebrate another year of local conservation work with Presumpscot Regional Land Trust at Randall Orchards in Standish. The gathering will highlight projects including improvements at East Windham Conservation…

Fri, Oct 23, 2026 at 10:00 am

Storytime Walk at Pride Preserve

Pride Preserve · Sebago Lakes Region

Join Presumpscot Regional Land Trust and Westbrook Public Library for nature story time at Pride Preserve in Westbrook. The event will begin with a welcome story or song…

Sat, Oct 24, 2026 at 5:30 pm

Frightening Festival of Fun!

George E. Jack School · Standish

Celebrate Halloween with a free evening of family fun presented by Standish Parks & Recreation. Costumes are strongly encouraged, and the event is open to everyone on or…

Sun, Oct 25, 2026 at 11:00 am

Fall Fest at Orchard Ridge Farm

Orchard Ridge Farm · Gorham

Celebrate the season at Orchard Ridge Farm with a festive afternoon featuring 30 Maine makers and artists, live music, two food trucks, hot apple cider and cider donuts,…

Fri, Oct 30, 2026 at 5:00 pm

Pumpkins in the Park & Outdoor Movie Night

Tassel Top Park · Raymond

Celebrate Halloween by the lake with a family evening of pumpkin decorating and an outdoor movie at Tassel Top Park.Families will receive a pumpkin and decorating supplies, with…

Sat, Nov 7, 2026 at 9:00 am

WCA Craft Fair & Silent Auction

Windham Christian Academy · Windham, Maine

Shop from local crafters and vendors at Windham Christian Academy’s public Craft Fair & Silent Auction.Browse handmade and locally offered goods, place bids in the silent auction, and…

Sun, Nov 8, 2026 at 10:00 am

Orienteering and Scavenger Hunt at Windham Community Forest

Windham Community Forest – Lowell Farm Trailhead · Windham

Walk or run through the woods searching for bright orange flags nestled among the trees, rocks, and rivers at Lowell Preserve. Serious orienteers will have fun following their…

Sat, Dec 5, 2026 at 9:45 am

Santa Shuffle 5K

7 Nulty Street · Bridgton, Maine

Celebrate the season with a family-friendly run and walk in Bridgton while supporting children at the Bridge Crossing.The morning begins with a free Kids Fun Run at 9:45…