Memorial Day Weekend 2026 in the Sebago Lake Region
By Sebago Lake Lovin
Businesses around the lake are expanding hours for the holiday weekend, more live entertainment is returning, and many local favorites are now fully open heading into summer.
A huge thank you to our presenting partners: Chianti Italian Cuisine and Gary's Olde Towne Tavern.
Gary's Olde Towne Tavern Kicks Off Summer Entertainment
The party starts Thursday night and rolls all weekend long at Gary's in Naples.
Thursday Night (May 21)
Gary-Oke Karaoke Night returns at 8PM.
Friday Night (May 22)
The DJs take over with the Friday Night Dance Party at 8PM.
Saturday Night (May 23)
LIVE BANDS ARE BACK at Gary's with 3 Day Funk taking the stage at 8PM for the return of live band season.
Music on Main Returns to Bridgton
One of the Lakes Region's favorite summer traditions is officially BACK.
Music on Main returns Saturday night in downtown Bridgton with EagleMania kicking off the 2025 season at 6PM.
Bring your lawn chairs, walk Main Street, and enjoy one of the signature summer nights in the Sebago Lake Region.
Looking for even more to do this Memorial Day Weekend?
Browse live music, nightlife, family activities, lake events, and more on the Sebago Lake Lovin Events Calendar.
Special "Napoli to Naples" Dinner Experience at The Hamilton House
On Friday, May 22, The Hamilton House is hosting a special "Napoli to Naples, Maine" Authentic Italian Cocktail Reception & Dinner Experience featuring a chef from Naples, Italy serving authentic Italian cuisine in an intimate sit-down setting.
Freedom Café & Pub Has Live Music This Weekend
Freedom Café & Pub continues its live music lineup this weekend with Music with Carlos on Saturday at 5:30PM.
Olde Mill Tavern Has A Full Weekend of Entertainment
Olde Mill Tavern in Harrison also has live entertainment throughout the holiday weekend.
Friday
Drunk in Public (7PM–10PM)
Saturday
Roundabout (7PM–10PM)
Sunday
Karayucky (6PM–9PM)
Boating Season Is Officially Underway
With Memorial Day Weekend here, expect plenty of activity out on Sebago Lake and the surrounding waterways as boaters return for the unofficial start of summer.
And just a reminder that the Songo Lock closes at 5:30PM, which is the last time for boats to go through.
Boat launches are open around the lake, including Sebago Lake State Park as well as the public ramp in Raymond.
More Live Music Happening Around the Region
Captain Jack's
Six Wayz to Sunday — Friday at 7PM
Michael Krapovicky — Saturday at 2PM
Lakes Region Brewing
Terry Swett — Friday at 6PM
Erik's Church
Sugarbox — Friday at 8PM
Larry Williams Band — Saturday at 8PM
Don't Miss Anything This Weekend
The Sebago Lake Region calendar is filling up fast as the season gets underway. Find upcoming events, entertainment, dining specials, and local happenings all in one place.