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…

Sun, Oct 18, 2026 at 2:00 pm

Explorations — Casco Bay Wind Symphony

McCormack Performing Arts Center at Gorham High School · Gorham, Maine

Join Casco Bay Wind Symphony for Explorations, a public concert featuring musical journeys across Earth and beyond, with works by John Mackey, Dana Wilson, David Gillingham and John…

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 11:00 am

Little Duck 50K and 10K Trail Running Race

East Windham Conservation Area · Sebago Lakes Region

Sun, Oct 18, 2026 at 10:00 am

Gorham Heritage Day

Cherry Hill Farm · Gorham, Maine

We’re celebrating Gorham’s 290th birthday with the Gorham Historical Society! The first annual Gorham Heritage Day will commemorate the town’s founding and will feature historical exhibits, cook-offs, and…

Sat, Oct 17, 2026 at 2:00 pm

Go Outside Gorham – Fall Fest at Robie Park

Robie Park · Gorham, Maine

Enjoy a fall afternoon at Robie Park with games, activities, music, a petting zoo and food trucks. Presumpscot Regional Land Trust will share information about local outdoor recreation…

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,…

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 10:00 am

Family Fun Makers Day

Denmark Arts Center · Denmark, Maine

Enjoy a free, public fall family program at Denmark Arts Center for ages 5 and older. Sam Smith of the Maine Blacksmith Guild will demonstrate blacksmithing in the…

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 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,…

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…

Fri, Oct 16, 2026 at 9:00 am

History Walks: Narramissic & Peabody-Fitch Woods

Narramissic Historical Farm & Peabody-Fitch Woods · Bridgton, Maine

Join Loon Echo Land Trust and Bridgton Historical Society for a guided walk at Narramissic Historical Farm and Peabody-Fitch Woods in South Bridgton. Explore the history of the…

Thu, Oct 15, 2026 at 1:00 pm

7th Annual Great Northern Docks Food Drive with the Maine Cabin Masters

Great Northern Docks · Naples, Maine

Meet the Maine Cabin Masters crew—Chase, Ashley, Ryan, Dixie and Jedi—while helping neighbors in need at Great Northern Docks’ seventh annual food drive in Naples.Thursday, October 15, 2026,…

Wed, Oct 14, 2026 at 3:00 pm

Pumpkin Decorating Day

Lakes Region Recovery Center · Bridgton, Maine

Join Lakes Region Recovery Center in Bridgton for a seasonal pumpkin-decorating gathering. Decorate a pumpkin for Halloween and enjoy cookies, treats and community company.Wednesday, October 14, 2026, starting…

Sun, Oct 11, 2026 at 11:00 am

Saco River Wildlife Center Anniversary Carnival

Steep Falls Village Park · Standish, Maine

Celebrate Saco River Wildlife Center’s 11th anniversary at its second annual family carnival in Steep Falls. Enjoy live music by Stella Blue Brothers, a bounce house, face painting,…

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 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…

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 11:00 am

Fall Festival at Pleasant Mountain

Pleasant Mountain · Bridgton, Maine

Celebrate autumn at Pleasant Mountain with scenic chairlift rides, live music, pumpkin painting, fall games for children and a bounce house. Local brews, oysters, chili, donuts and snacks…

Sat, Oct 10, 2026 at 10:00 am

Wellness Expo for Wishes

The Roosevelt Room at Dormir Hotel · Windham, Maine

The Roosevelt Room at Dormir Hotel presents Mind, Body + Soul: Wellness Expo for Wishes, bringing together medical, holistic, mental and physical wellness professionals to benefit Make-A-Wish Maine.…

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…

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…

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,…

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…

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…

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,…

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…

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…

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…

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 1:00 pm

Watercolor Workshop — Beginners Welcome at Hawthorne House

Nathaniel Hawthorne’s Boyhood Home · Raymond

Beginners are welcome at this hands-on watercolor workshop with instructor Kathleen Gerdes at Nathaniel Hawthorne’s Boyhood Home. The $35 registration fee includes all student supplies and materials. The…

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…

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…

Mon, Sep 21, 2026 at 3:00 pm

Public Safety Open House

Central Station/Public Safety Building · Windham, Maine

Meet Windham’s local firefighters, EMTs, police officers, staff, and volunteers during a free afternoon focused on public safety and family fun.Activities include food trucks, Touch-a-Truck, K9 demonstrations, raffles…

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…

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.…

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 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 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…

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…

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…

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…

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

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…

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…

Wed, Sep 9, 2026 at 3:00 pm

Sebago Community Market — September 9

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…

Sun, Sep 6, 2026 at 11:00 am

Ultimate Eric Church Experience at Causeway Marina

Causeway Marina · Naples, Maine

Enjoy free live waterfront music at Causeway Marina in Naples, headlined by Tim Gleason’s Ultimate Eric Church Experience. The opening band performs from 11:00 a.m. to 1:30 p.m.,…

Sat, Sep 5, 2026 at 7:30 pm

Classic Rock Sunset Dance Cruise

Songo River Queen II · Naples, Maine

Cruise Long Lake aboard the Songo River Queen II during a two-hour sunset dance cruise featuring a DJ playing 1970s and 1980s favorites. Guests can request songs while…

Sat, Sep 5, 2026 at 4:30 pm

Benefit Turkey Supper for Scholarships

Sebago Town Hall · Sebago

Support local students at a community turkey supper benefiting two $1,000 scholarships for 2027 Lake Region graduates from Sebago. The complete dinner includes turkey and gravy, mashed potato,…

Fri, Sep 4, 2026 at 7:00 pm

Motor Booty Affair’s Booty Booze Cruise

Songo River Queen II · Naples, Maine

Climb aboard the Songo River Queen II for a 21+ Booty Booze Cruise featuring a live disco show by Motor Booty Affair. Doors open at 6:00 p.m., and…

Thu, Sep 3, 2026 at 6:00 pm

Sebago Watershed Shoreland Protection–Panel Discussion (Hawthorne House)

Hawthorne House · Raymond

The Hawthorne House is hosting a panel presentation about the current state of the Sebago Watershed, the organizations that support its water quality, and the challenges that they…

Thu, Sep 3, 2026 at 12:00 pm

The Crooked River Gathering

Ossipee Valley Fairgrounds and Crooked River Woodlands · Hiram, Maine

Celebrate bluegrass and old-time music, camping, farming, homesteading, and artisan creativity over Labor Day weekend. The four-day gathering features live music, a farm and artisan market, food trucks,…

Wed, Sep 2, 2026 at 3:00 pm

Sebago Community Market — September 2

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…

Mon, Aug 31, 2026 at 9:00 am

2026 Camp Sunshine Shootout

Point Sebago Golf Course · Casco, Maine

Tee off for a purpose at the 2026 Camp Sunshine Shootout, a charity golf tournament at Point Sebago Resort. Enjoy 18 holes of golf, contests, raffle prizes, on-course…

Sun, Aug 30, 2026 at 7:00 am

Bald Pate 10K & Five Fields Farm 50K

Five Fields Farm · Bridgton, Maine

Choose between two challenging trail races benefiting Loon Echo Land Trust. The Five Fields Farm 50K follows a three-lap course through the Bald Pate and Holt Pond preserves,…

Sat, Aug 29, 2026 at 7:30 pm

Shanna in a Dress at The Hayloft

The Hayloft at Dragonfly Barn · Bridgton, Maine

Enjoy an evening with Shanna in a Dress at The Hayloft at Dragonfly Barn. Her performance blends witty, heartfelt songwriting with folk-pop storytelling in an intimate listening-room setting.…

Sat, Aug 29, 2026 at 4:30 pm

Casco Village Church Summer BBQ Picnic Supper

Casco Village Church United Church of Christ · Casco, Maine

Enjoy a community summer barbecue picnic supper at Casco Village Church UCC. The menu includes chicken, pork, burgers, hot dogs, salads, corn on the cob, beans, watermelon, and…

Sat, Aug 29, 2026 at 1:00 pm

3rd Annual Salsa on the Songo: LFC Lake Edition

Songo River Queen II · Naples, Maine

Dance on Long Lake during a 2.5-hour salsa cruise aboard the Songo River Queen II. Music begins during boarding at 1:00 p.m., followed by a 1:30–4:00 p.m. cruise…

Sat, Aug 29, 2026 at 1:00 pm

Steamboat Willie’s Ribbon Cutting

9 Morningside Lane, Casco, ME 04015 · Sebago Lakes Region

Join Us for Steamboat Willie’s Opening Celebration & Ribbon Cutting! 🎉 Come celebrate a new adventure on the water with Steamboat Willie’s Sebago Fishing & Recreational Guide Services!…

Sat, Aug 29, 2026 at 10:00 am

2026 Cardboard Regatta

Kiwanis Beach · Standish, Maine

Build a boat from cardboard and bring it to Kiwanis Beach for the 2026 Cardboard Regatta. This public community event invites participants and spectators to enjoy a creative…

Fri, Aug 28, 2026 at 7:00 pm

The Powerhouse Five Live on Long Lake

Songo River Queen II · Naples, Maine

Cruise Long Lake aboard the Songo River Queen II while The Powerhouse Five perform a lively mix of rock, pop, dance, and country favorites. The floating concert departs…

Fri, Aug 28, 2026 at 5:30 pm

3rd Annual Friday Night Stitch Night

Bridgton Community Center · Bridgton, Maine

Bring a knitting, crochet, embroidery, quilting, spinning, or other fiber-arts project for an evening of stitching, conversation, and community at the Bridgton Community Center.This annual potluck gathering includes…

Thu, Aug 27, 2026 at 5:30 pm

Ladies Movie Night!  The Scarlet Letter (Hawthorne House)

Sebago Lakes Region

Ladies Movie Night featuring The Scarlet Letter starring Demi Moore, Gary Oldman, and Robert Duvall. All ladies are invited to view the 1995 adaptation of the classic Hawthorne…

Thu, Aug 27, 2026 at 5:00 pm

A Special Evening with Two-Time Newbery Medalist Lois Lowry

The Graham Center at RPM, 121 Main Street, Bridgton, Maine, 04009, United States · Sebago Lakes Region

The Rufus Porter Museum of Art & Ingenuity is excited to welcome world-renowned author — and valued museum member — Lois Lowry for an intimate presentation, A Writer’s…

Thu, Aug 27, 2026 at 10:00 am

All-Ages Story Time & Fun: A Frog in the Bog

Richville Library · Standish, Maine

Join Richville Library for an all-ages story time featuring “A Frog in the Bog” by Karma Wilson and Joan Rankin. The morning will include singing rhymes, a craft,…

Thu, Aug 27, 2026

Maine Folk Presents Camping at Camp Hinds

Camp William Hinds · Raymond, Maine

Spend a long weekend at Camp William Hinds for a gathering of music, performance arts, makers, camping, and community. Maine Folk brings together performers, creators, families, and merrymakers…

Wed, Aug 26, 2026 at 3:00 pm

Sebago Community Market — August 26

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…

Tue, Aug 25, 2026 at 5:30 pm

Yoga on the Hill

Hacker’s Hill Preserve · Casco, Maine

Join Loon Echo Land Trust for a gentle outdoor yoga practice at the top of Hacker’s Hill. Certified instructors will guide participants through postures and sequences in the…

Mon, Aug 24, 2026 at 4:00 pm

ROCK O-At-Ka Benefit Concert

Camp O-AT-KA · Sebago, Maine

Enjoy an evening of live music at Camp O-AT-KA benefiting Spaulding Memorial Library. Bold Riley and 3 Day Funk will perform, and Sylvia’s Mobile Catering will provide separate…

Fri, Aug 21, 2026 at 6:00 pm

Strike a Chord with History

Standish Municipal Building · Standish, Maine

Go back in time at a fun-filled concert featuring the Lakes Region Strummers, a ukulele-based band. Enjoy favorite rock-and-roll hits that revive the classic 1920s American ukulele craze…

Fri, Aug 21, 2026 at 10:00 am

Book Club: Dare to Lead by Brené Brown

Sebago Lakes Region

📚 Chamber Book Club: Dare to Lead by Brené Brown Join fellow Chamber members as we explore Dare to Lead by Brené Brown, a thought-provoking book about what…