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Outdoor Events and Things to do in Gloucester, MA

Fantasy Ride: Launch Experience
Sat, Jun 27, 7:30 PM
Everett · Encore Boston Harbor
Fantasy Ride: Launch Experience
Sat, Jun 27, 7:30 PM
Everett · Encore Boston Harbor
Going fast
BVS' Summer Biotech Community Celebration at Tech Square, Cambridge
Thu, Jun 4, 4:00 PM
Cambridge · Tech Square Courtyard
Going fast
BVS' Summer Biotech Community Celebration at Tech Square, Cambridge
Thu, Jun 4, 4:00 PM
Cambridge · Tech Square Courtyard
Going fast
Middle Reservoir Loop Hike
Fri, Jun 5, 1:00 PM
Winchester · Long Pond Parking Lot
Going fast
Middle Reservoir Loop Hike
Fri, Jun 5, 1:00 PM
Winchester · Long Pond Parking Lot
Spectacle Island Caribbean American Boat Cruise
Sun, Jun 28, 12:00 PM
Boston · Long Wharf
Spectacle Island Caribbean American Boat Cruise
Sun, Jun 28, 12:00 PM
Boston · Long Wharf
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
Cannah Buttah Babe Presents: The Sinners Dinner Party
Fri, Jun 19, 6:00 PM
MEDFORD · Medford
Cannah Buttah Babe Presents: The Sinners Dinner Party
Fri, Jun 19, 6:00 PM
MEDFORD · Medford
Revival - Boston's BIPOC PRIDE BAR FETE
Sat, Jun 6, 2:00 PM
Boston · Apex Rooftop Bar and Lounge
Revival - Boston's BIPOC PRIDE BAR FETE
Sat, Jun 6, 2:00 PM
Boston · Apex Rooftop Bar and Lounge
The Bee Hive Block Party
Saturday at 11:00 AM
Boston · Dante Alighieri Montessori School
The Bee Hive Block Party
Saturday at 11:00 AM
Boston · Dante Alighieri Montessori School
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Tomorrow at 6:00 PM + 14 more
Andover · 90 Harold Parker Rd
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Tomorrow at 6:00 PM + 14 more
Andover · 90 Harold Parker Rd
Camp Spectacle
Fri, Jul 31, 4:00 PM
Boston · Spectacle Island
Camp Spectacle
Fri, Jul 31, 4:00 PM
Boston · Spectacle Island
Boston Pride for the People Parade
Sat, Jun 6, 11:00 AM
Boston · Copley Square
Boston Pride for the People Parade
Sat, Jun 6, 11:00 AM
Boston · Copley Square
Sales end soon
Sip & Sculpt on the Patio Workshop
Sunday at 1:00 PM
Boston · Downeast Cider House
Sales end soon
Sip & Sculpt on the Patio Workshop
Sunday at 1:00 PM
Boston · Downeast Cider House
Bulfinch Triangle Walking Tour
Sat, Jun 20, 11:00 AM
Boston · The West End Museum
Bulfinch Triangle Walking Tour
Sat, Jun 20, 11:00 AM
Boston · The West End Museum
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
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
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
Almost full
The 2nd Incredible Summer Boat Tour: Massport’s Strategy for Boston Harbor!
Fri, Jun 26, 1:30 PM
Cambridge · 100 Cambridgeside Pl
Almost full
The 2nd Incredible Summer Boat Tour: Massport’s Strategy for Boston Harbor!
Fri, Jun 26, 1:30 PM
Cambridge · 100 Cambridgeside Pl
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
Sales end soon
New England Hong Kong Festival 2026
Saturday at 11:00 AM
Somerville · Seven Hills Park
Sales end soon
New England Hong Kong Festival 2026
Saturday at 11:00 AM
Somerville · Seven Hills Park
Single Mingle: Seaport Patio Edition
Thu, Jun 11, 6:30 PM
Boston · City Tap House Boston
Single Mingle: Seaport Patio Edition
Thu, Jun 11, 6:30 PM
Boston · City Tap House Boston

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