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Summer Events and Things to do in Gloucester, MA

Jeff Beam & Aedan Macdougall live on the Bayside Bowl Roof | all-ages
Thu, Jul 23, 6:00 PM
Portland · Bayside Bowl
Jeff Beam & Aedan Macdougall live on the Bayside Bowl Roof | all-ages
Thu, Jul 23, 6:00 PM
Portland · Bayside Bowl
Just added
Telescope Observing Night
Tuesday at 9:30 PM
Providence · Ladd Observatory
Just added
Telescope Observing Night
Tuesday at 9:30 PM
Providence · Ladd Observatory
Grammy Winner Dave Gutter live on the Bayside Bowl Roof | all-ages
Thu, Sep 3, 6:00 PM
Portland · Bayside Bowl
Grammy Winner Dave Gutter live on the Bayside Bowl Roof | all-ages
Thu, Sep 3, 6:00 PM
Portland · Bayside Bowl
Just added
Paint Night - Spring Bouquets
Thu, May 14, 5:30 PM
Portland · Root Wild Kombucha
Just added
Paint Night - Spring Bouquets
Thu, May 14, 5:30 PM
Portland · Root Wild Kombucha
ROOF CLOSING PARTY: Gina & The Red Eye Flight Crew | all-ages
Thu, Sep 24, 6:00 PM
Portland · Bayside Bowl
ROOF CLOSING PARTY: Gina & The Red Eye Flight Crew | all-ages
Thu, Sep 24, 6:00 PM
Portland · Bayside Bowl
Red Day 2026
Thu, May 14, 9:30 AM
Hanson · 526 Indian Head St
Red Day 2026
Thu, May 14, 9:30 AM
Hanson · 526 Indian Head St
Breath.Sound.Sweat.
Wed, May 20, 6:00 PM
Portland · Good Medicine Collective
Breath.Sound.Sweat.
Wed, May 20, 6:00 PM
Portland · Good Medicine Collective
Little Lies (Fleetwood Mac Tribute) live at Bayside Bowl | all-ages
Fri, Jul 24, 8:00 PM
Portland · Bayside Bowl
Little Lies (Fleetwood Mac Tribute) live at Bayside Bowl | all-ages
Fri, Jul 24, 8:00 PM
Portland · Bayside Bowl
Almost full
Little Lies | Fleetwood Mac Tribute + Dinner
Tomorrow at 6:00 PM
Sturbridge · The Barn at Wight Farm
Almost full
Little Lies | Fleetwood Mac Tribute + Dinner
Tomorrow at 6:00 PM
Sturbridge · The Barn at Wight Farm
☀️ Summer Hand Glass Etching
Sun, May 17, 1:00 PM
Swanzey · Frogg Brewing
☀️ Summer Hand Glass Etching
Sun, May 17, 1:00 PM
Swanzey · Frogg Brewing
Hannah Cohen
Sat, Jun 27, 8:00 PM
Portland · SPACE
Hannah Cohen
Sat, Jun 27, 8:00 PM
Portland · SPACE
Sales end soon
Intuitive Painting at Wild Willow Farm
Saturday at 3:00 PM
Franklin · Wild Willow Farm
Sales end soon
Intuitive Painting at Wild Willow Farm
Saturday at 3:00 PM
Franklin · Wild Willow Farm
Sunken Suite 2026
Fri, Jul 17, 4:00 PM
Sturbridge · Sturbridge Host Hotel & Conference Center
Sunken Suite 2026
Fri, Jul 17, 4:00 PM
Sturbridge · Sturbridge Host Hotel & Conference Center
3rd Annual Little Pirates 3-Day Surfcamp
Wed, Jul 15, 10:00 AM
Westport · Horseneck Beach
3rd Annual Little Pirates 3-Day Surfcamp
Wed, Jul 15, 10:00 AM
Westport · Horseneck Beach
Intro to Watercolors - August 2026
Wed, Aug 5, 6:00 PM
Portland · 105 St James St
Intro to Watercolors - August 2026
Wed, Aug 5, 6:00 PM
Portland · 105 St James St
Sales end soon
Sound Bath at Wild Willow Farm with Brandi from Phases of Light
Sunday at 5:00 PM
Franklin · Wild Willow Farm
Sales end soon
Sound Bath at Wild Willow Farm with Brandi from Phases of Light
Sunday at 5:00 PM
Franklin · Wild Willow Farm
The Bug Club
Mon, Jun 29, 7:30 PM
Portland · SPACE
The Bug Club
Mon, Jun 29, 7:30 PM
Portland · SPACE
Almost full
Herb Container Garden Workshop
Friday at 4:00 PM
West Brookfield · The Joy of Beans Coffee
Almost full
Herb Container Garden Workshop
Friday at 4:00 PM
West Brookfield · The Joy of Beans Coffee
A Day with Spirit and Wellness
Sat, May 9, 10:00 AM
Franklin · Wild Willow Farm
A Day with Spirit and Wellness
Sat, May 9, 10:00 AM
Franklin · Wild Willow Farm
Dreamline: A Tight Cruise Pre-Party
Fri, May 15, 9:00 PM
Providence · Platforms Dance Club
Dreamline: A Tight Cruise Pre-Party
Fri, May 15, 9:00 PM
Providence · Platforms Dance Club

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