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Outdoor Events and Things to do in Gloucester, MA

Almost full
Middle Reservoir Loop Hike
Friday at 1:00 PM
Winchester · Long Pond Parking Lot
Almost full
Middle Reservoir Loop Hike
Friday at 1:00 PM
Winchester · Long Pond Parking Lot
Taylor Swift Eras & Bridal/Bach Party Boston | Seaport Summer Cruise
Fri, Jun 26, 6:30 PM
Boston · Provincetown II Yacht
Taylor Swift Eras & Bridal/Bach Party Boston | Seaport Summer Cruise
Fri, Jun 26, 6:30 PM
Boston · Provincetown II Yacht
UAFRICA Music Festival featuring BNXN, Tyler ICU & more
Sat, Jul 25, 3:00 PM
Boston · The Yard Charlestown
UAFRICA Music Festival featuring BNXN, Tyler ICU & more
Sat, Jul 25, 3:00 PM
Boston · The Yard Charlestown
Explore Malden Center’s Public Art – Walking Tour
Tue, Jun 16, 6:00 PM
Malden · Malden Center MBTA Station
Explore Malden Center’s Public Art – Walking Tour
Tue, Jun 16, 6:00 PM
Malden · Malden Center MBTA Station
Paint & Sip Night: Wine Glass Painting, Wine & Women Entrepreneurs
Fri, Jul 10, 5:30 PM
Haverhill · Willow Spring Vineyards
Paint & Sip Night: Wine Glass Painting, Wine & Women Entrepreneurs
Fri, Jul 10, 5:30 PM
Haverhill · Willow Spring Vineyards
Camp Spectacle
Fri, Jul 31, 4:00 PM
Boston · Spectacle Island
Camp Spectacle
Fri, Jul 31, 4:00 PM
Boston · Spectacle Island
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Tomorrow at 6:00 PM + 13 more
Andover · 90 Harold Parker Rd
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Tomorrow at 6:00 PM + 13 more
Andover · 90 Harold Parker Rd
Spectacle Summer Nights
Sat, Jul 18, 4:00 PM
Boston · Spectacle Island
Spectacle Summer Nights
Sat, Jul 18, 4:00 PM
Boston · Spectacle Island
Seaport Summer Cruise Series | Best Floating Party in Boston
Sat, Jun 20, 6:30 PM
Boston · Provincetown II Yacht
Seaport Summer Cruise Series | Best Floating Party in Boston
Sat, Jun 20, 6:30 PM
Boston · Provincetown II Yacht
Forests of Alnoba with Harold Bragg-July 2026
Tue, Jul 21, 10:00 AM
Kensington · Alnoba
Forests of Alnoba with Harold Bragg-July 2026
Tue, Jul 21, 10:00 AM
Kensington · Alnoba
Anything Goes On The Water
Sat, Jul 4, 10:30 AM
Boston · 60 Rowes Wharf
Anything Goes On The Water
Sat, Jul 4, 10:30 AM
Boston · 60 Rowes Wharf
Going fast
WOOF - Pride Block Party!
Saturday at 2:00 PM
Boston · Jacques' Cabaret
Going fast
WOOF - Pride Block Party!
Saturday at 2:00 PM
Boston · Jacques' Cabaret
90's Night DJ moonlight Cruise
Fri, Jun 26, 9:00 PM
Boston · Mass Bay Lines
90's Night DJ moonlight Cruise
Fri, Jun 26, 9:00 PM
Boston · Mass Bay Lines
Almost full
Danis Queer Bar Pride Block Party
Saturday at 1:00 PM
Boston · Gloucester Street
Almost full
Danis Queer Bar Pride Block Party
Saturday at 1:00 PM
Boston · Gloucester Street
Devri's Annual Harbor Cruise
Sat, Aug 8, 12:30 PM
Boston · Bay State Cruise Company
Devri's Annual Harbor Cruise
Sat, Aug 8, 12:30 PM
Boston · Bay State Cruise Company
Sales end soon
Boston Pride for the People Parade
Saturday at 11:00 AM
Boston · Copley Square
Sales end soon
Boston Pride for the People Parade
Saturday at 11:00 AM
Boston · Copley Square
Afrique Records Presents: The Reminisce, A Sunset Cruise by Boston Harbor
Sun, Jun 21, 5:00 PM
Boston · 60 Rowes Wharf
Afrique Records Presents: The Reminisce, A Sunset Cruise by Boston Harbor
Sun, Jun 21, 5:00 PM
Boston · 60 Rowes Wharf
Island escape
Sat, Jun 27, 12:00 PM
Boston · Rowes Wharf
Island escape
Sat, Jun 27, 12:00 PM
Boston · Rowes Wharf
Jewish Downtown, Boston Movie Series - The Rabbi's Cat
Wed, Jun 10, 7:00 PM
Boston · The Boston Synagogue
Jewish Downtown, Boston Movie Series - The Rabbi's Cat
Wed, Jun 10, 7:00 PM
Boston · The Boston Synagogue
Champions Island
Sun, Aug 9, 3:00 PM
Boston · Georges Island
Champions Island
Sun, Aug 9, 3:00 PM
Boston · Georges Island

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