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…

Wed, Sep 9, 2026 at 8:00 pm

Hacker’s Hill Open for 9/11 Honor Summit Viewing

Hacker’s Hill Preserve · Casco, Maine

Loon Echo Land Trust is providing special evening access to Hacker’s Hill Preserve so visitors can view the illuminated 9/11 Honor Summit memorial on Mount Washington. Two beams…

Sat, Sep 12, 2026

11th Annual Sebago Lake Togue (Lake Trout) & Pike Derby

Point Sebago Resort Docks · Casco, Maine

A two-day fishing derby on Sebago Lake sponsored by the Sebago Lake Anglers Association. The official weigh-in is at Point Sebago Resort Docks. Maine Inland Fisheries & Wildlife…

Sat, Sep 12, 2026 at 10:00 am

2nd Annual Roosevelt Trail History Tour

Museums and historic sites along Roosevelt Trail (Route 302) · Sebago Lake Region, Maine

Explore rural history along Roosevelt Trail (Route 302) during this free, self-guided auto or bicycle tour. Visit one, several, or all of the participating museums and historic sites…

Sat, Sep 12, 2026 at 12:00 pm

Patty’s Pontoon Boat Day

Long Beach Marina · Sebago, Maine

Operation Ray of Light and Long Beach Marina invite veterans and their families to a free afternoon on Sebago Lake. Long Beach Marina is providing its pontoon fleet…

Wed, Sep 16, 2026 at 3:00 pm

Sebago Community Market — September 16

Sebago Community Market · Sebago, Maine

Shop local at the Sebago Community Market, featuring a rotating selection of local farmers, businesses, bakers, makers, artisans, and food trucks. Offerings vary by week and may include…

Fri, Sep 18, 2026 at 4:30 pm

Sebago Lake Rotary Lobster Roll Fundraiser

Windham Veterans Center · Windham

Celebrate Maine Lobster Week while supporting the Sebago Lake Rotary Club at this drive-through lobster roll dinner fundraiser. Each $25 meal includes a lobster roll, coleslaw, chips, and…

Sat, Sep 19, 2026 at 7:45 am

17th Annual Rotary Charity Golf Classic

Bridgton Highlands Golf and Tennis · Bridgton, Maine

Join the Bridgton-Lake Region Rotary Club for its 17th Annual Charity Golf Classic at Bridgton Highlands Golf and Tennis. Golfers and sponsors are invited for a day on…

Sat, Sep 19, 2026 at 9:30 am

Woodland Owner Appreciation Day 2026

Camp Skylemar · Naples

Woodland owners with 10 or more acres in the Lake Region are invited to a free day of guided forest walks, expert talks, resource sharing, and networking at…

Sat, Sep 19, 2026 at 11:30 am

Bands Behind the Barn 2026

Hearts & Horses Therapeutic Riding Center · Buxton

Spend the day enjoying live music, food trucks, raffles, a silent auction, games, and Horse Poop Bingo at Hearts & Horses’ annual Bands Behind the Barn fundraiser. Proceeds…

Sat, Sep 19, 2026 at 4:00 pm

Community Bean Supper at The Deeper Well Church

The Deeper Well Church · Standish, Maine

Gather for good food, fellowship, and community at The Deeper Well Church's public bean supper in Standish. Dinner includes beans, red snappers, rolls, coleslaw, dessert, and a drink.…

Sun, Sep 20, 2026 at 9:00 am

Harvest Hills 20th Annual Golf & Tennis Tournament

Bridgton Highlands Golf and Tennis · Bridgton, Maine

Support Harvest Hills Animal Shelter at its 20th annual Golf & Tennis Tournament. The fundraiser takes place at Bridgton Highlands and offers golf and tennis in support of…

Wed, Sep 23, 2026 at 12:00 pm

Veterans Cruise aboard the Songo River Queen II

Songo River Queen II · Naples, Maine

The Wounded Heroes Program of Maine invites veterans on a free 90-minute cruise aboard the Songo River Queen II. The cruise includes live music, and refreshments will be…

Thu, Sep 24, 2026 at 2:30 pm

Storytime Walk at Lowell Preserve

Lowell Preserve · Sebago Lakes Region

Join Presumpscot Regional Land Trust and Windham Public Library for a nature story time at Lowell Preserve in Windham. The program will be led by Children’s Librarian Samantha…

Fri, Sep 25, 2026 at 5:30 pm

Paint & Sip: Paint Your Partner

Frye Island Leisure Lounge · Frye Island

Grab a glass, bring your partner, and try to capture each other on canvas at this lighthearted Paint & Sip at the Frye Island Leisure Lounge. Expect crooked…

Fri, Sep 25, 2026 at 6:00 pm

The Beatles Candlelight Experience

First Congregational Church UCC · Bridgton, Maine

Experience a classical tribute to The Beatles performed by a string trio in an intimate candlelit setting. Two one-hour performances are offered: the first sitting runs from 6:00…

Sat, Sep 26, 2026 at 9:00 am

Sharon’s Stroll ’26

Better Fit Fitness Center · Standish, Maine

Join Sharon’s Stroll for a 2.5-mile community road walk beginning at Better Fit Fitness Center. The annual fundraiser supports local groups and individuals affected by cancer and similar…

Sat, Sep 26, 2026 at 3:00 pm

Casco’s 1st Annual Community Fest

Casco Community Park · Casco, Maine

Join the Town of Casco for its first annual Community Fest at Casco Community Park. This save-the-date community celebration is scheduled for Saturday, September 26, from 3:00 to…

Wed, Sep 30, 2026 at 8:30 am

Sebago Lakes Region Fuller Center for Housing Golf Tournament

Spring Meadows Golf Club · Gray, Maine

Play in a charity golf tournament benefiting the Sebago Lakes Region Fuller Center for Housing. Proceeds support local home-repair projects for veterans and older adults, including accessibility ramps,…

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 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,…

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 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…

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…