June 20 @ 12:00 pm – 9:00 pm
Join the community for one of the region’s favorite summer traditions — Windham Summerfest 2026! This year’s theme, “Celebrating Sun, Stars, & Stripes,” promises a fun-filled day for all ages with live music, family activities, local crafters and vendors, delicious food booths hosted by non-profits, and plenty of community spirit. Best of all, this event is completely FREE to attend!
Summerfest is more than just a celebration — it’s a reflection of the strong community connections that make the Sebago Lakes Region so special. This event is made possible through the generosity, support, and involvement of local businesses, organizations, and volunteers who come together to create a memorable experience for residents and visitors alike.
We encourage Chamber members and local businesses to get involved by volunteering or sponsoring part of the event. Sponsorship opportunities are a wonderful way to showcase your business while helping keep this beloved tradition free and accessible for everyone.
Sponsorship Opportunities
Come celebrate summer, community, and local pride with us at Windham Summerfest 2026! The chamber will have a booth as well- more information to come!
June 3 @ 2:00 pm – 6:00 pm
Join us as we celebrate the opening of Fourteen Forty Financials’ second location with an Open House and Ribbon Cutting!
Fourteen Forty Financial specializes in advanced tax planning strategies, estate planning considerations, asset protection, and comprehensive wealth management.
We’re excited to welcome them to our Chamber community and to the Sebago Lakes Region, where they bring trusted local expertise and personalized financial guidance.
June 18 @ 5:00 pm – 7:00 pm
Reserve your spot today by filling out the form below! This price is JUST for MINI-GOLF. If you only plan to attend the social no purchase necessary and meet us outside where the picnic tables and cornhole boards are!
April 27 @ 7:00 pm – 8:00 pm
Come celebrate Windham’s rich history with the wonderful team at the Windham Historical Society! 📜
Join Libby Bischof, PhD, Executive Director of the Osher Map Library (OML) and Smith Center for Cartographic Edu cation (USM) for an informative talk about the ways the Windham area has been mapped from the 17th century to present!
With a featured discussion of Lothrop Snow’s 1802 Manuscript Map, “Plan of the last division of land in the town of Windham,” recently donated to the OML for restoration & preservation by the Windham Historical Society.
Attendees will also be able to see the newly conserved map in person.
Light refreshments served.
April 24 @ 6:00 pm – 10:00 pm
Step back into the Wild West for a fun-filled evening at Roosevelt Room Ranch!
Join us on Friday, April 24, 2026 from 6:00–10:00 PM for a lively “Wanted”-themed night featuring line dancing, games, and great company. Whether you’re a seasoned dancer or just looking for a fun night out, there’s something for everyone.
Your $12 admission (21+) includes light fare, with additional fun including horseshoes, cornhole, and a cash bar.
✨ Come dressed in your best Western attire—there may even be a reward for the best Dolly Parton lookalike!
Bring your friends and get ready for a boot-stompin’ good time!
April 24 @ 5:30 pm – 6:00 pm
You’re Invited!
We’re so excited to share something brand new with you… Vitality Room Clients & Sebago Lakes Region Chamber Members are hearing it FIRST!
*Because this is an invitation only event, there is no FB Event page to direct you to.
Vitality Room has officially partnered in the travel industry, and to celebrate, you’re invited to an exclusive VIP Travel Experience at Vitality Room!
Thursday, April 23 at 6:00 PM
Arrival 5:45-6:00. Gates close at 6:00 PM
This isn’t just an event… it’s the beginning of your next experience.
Space is limited!
RSVPs are required, first come, first serve.
Please RSVP by 4/20
It’s smooth sailing with Vitality Room… and we can’t wait to take you there.
*Can’t make it but still want info? Email Michelle@MBThrives.com
June 18 @ 11:00 am – 1:00 pm
September 11 @ 7:30 pm – 10:00 pm
Get ready for a season full of fun at Point Sebago Resort!
Their Spring and Fall themed weekends are back, featuring live entertainment—including Motor Booty Affair on September 11, 2026.
Events are exclusive to resort guests, and Maine residents receive 20% off their stay.
Call 800-655-1232 to book and check out the full themed weekend lineup at the link provided.
May 2 @ 4:00 pm – 7:00 pm
Looking to support higher education while gaining great visibility for your business?
Join Saint Joseph’s College on May 2nd at River Winds Farm & Estate!
Get ready for the ultimate Run for the Roses party as we celebrate the ‘Most Exciting Two Minutes in Sports’ – the 2026 Kentucky Derby. This is going to be a fun afternoon, and all the proceeds support Saint Joseph’s College student scholarships. Sip refreshing Mint Juleps in your finest fascinators and hats, place your bets on the winning horse, and bid on valuable auction items at this unforgettable party!
Entertainment includes a live DJ, photo booth, prizes for the best dressed, live and silent auction, and mock betting with one grand prize winner!
For refreshments there will be signature cocktails and a delicious derby fare, including Derby Beef Tenderloin Sliders, Sea Scallops wrapped in Bacon, Coconut Shrimp, Crispy Vegetable Spring Rolls, Cranberry Asiago Turkey Sliders, and MORE!
✨ Chamber Member Exclusive! ✨
Join Saint Joseph’s College of Maine for their beautiful Roses Scholarship Gala—and take advantage of a special $50 ticket (normally $150!) just for Sebago Lakes Region Chamber members.
Use code SJCROSES2026 and be part of an inspiring evening supporting local students. 🌹
March 27 @ 4:00 pm – 7:00 pm
Description by the owner: We really hope you will join us as we celebrate Zebralove’s 20th year of business! This is an important milestone – and one that was reached because of YOU. So if you have worked with us, referred someone our way, or simply followed along over the years – JOIN US TO CELEBRATE!
Friday, March 27th
4pm – 7pm
51 US-1, Suite B
(former Humpty Dumpty building)
Scarborough
Abracadabra Productions Performs 5pm – 6pm
This is no standing around awkward party – we’ll have great food provided by some of our client businesses, music and entertainment from other talented clients, giveaways, other local business owners to meet – all in a casual, comfortable environment at (yes, another client) Priority Learning right on Route 1 in Scarborough with plenty of parking. We’re not trying to sell it too hard here, but why wouldn’t you come by?! Just RSVP so we can be sure to have enough goodies! See you on the 27th!
May 2 @ 9:00 am – May 3 @ 3:00 pm
Come try before you buy at Richardson’s Open House & In-The-Water Boat Show!
Saturday: 9-4 and Sunday 10-3.
They’ll have the best boat brands available for demo.
Including:
-Bennington – the #1 selling pontoon brand in America with industry leading 10-year warranty!
-Chaparral & Robalo – the leading manufacturers of quality fiberglass boats!
-Lund – the fisherman’s favorite, and
-Sea-Doo personal watercrafts (PWC’s on display only, no demos).
Stop by their waterfront marina on beautiful Sebago Lake at 633 White’s Bridge Road, Standish. Try before you buy!
June 3 @ 2:00 pm – 6:00 pm
Mark your calendars and join the Cumberland County Federal Credit Union while they toss hunger to the curb this June!
Registration is now open for our 8th Annual Ending Hunger Bag Toss Tournament! The tournament will take place on Wednesday, June 3, 2026, at 33 Elmwood in Westbrook: https://33elmwoodme.com/
All proceeds from this event will be donated to the Maine Credit Unions’ Campaign for Ending Hunger.
To participate in the tournament or explore sponsorship opportunities, please contact the credit union directly to obtain the event registration form. For any questions about the tournament, you can reach them at 207-878-3441 or events@myccfcu.com
(207) 878-3441 x 222
dpmartin@myccfcu.com
