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Outdoor Events and Things to do in Gloucester, MA

Boston Grown-Ups Museum: Summer Camp Edition
Fri, Jun 26, 7:00 PM
Boston · Boston Children's Museum
Boston Grown-Ups Museum: Summer Camp Edition
Fri, Jun 26, 7:00 PM
Boston · Boston Children's Museum
Sales end soon
BMP Block Party 2026
Saturday at 11:00 AM
Boston · Rowes Wharf Plaza, Rose Kennedy Greenway
Sales end soon
BMP Block Party 2026
Saturday at 11:00 AM
Boston · Rowes Wharf Plaza, Rose Kennedy Greenway
Pride in Boston's Festival/Block Party Exhibitor Registration 2026
Saturday at 12:00 PM
Boston · Boston Common
Pride in Boston's Festival/Block Party Exhibitor Registration 2026
Saturday at 12:00 PM
Boston · Boston Common
Almost full
Entry to Elmendorf Grand Prix Seeded Sandwich Loaf Bread Competition
Sun, Jun 14, 12:00 PM
Cambridge · Elmendorf Baking Supplies & Cafe
Almost full
Entry to Elmendorf Grand Prix Seeded Sandwich Loaf Bread Competition
Sun, Jun 14, 12:00 PM
Cambridge · Elmendorf Baking Supplies & Cafe
Sales end soon
Lamplighter's Pride Patio Party
Saturday at 12:00 PM
Cambridge · Lamplighter Brewing Co. - CX
Sales end soon
Lamplighter's Pride Patio Party
Saturday at 12:00 PM
Cambridge · Lamplighter Brewing Co. - CX
Fells Trail Run Club
Sunday at 10:00 AM + 1 more
Winchester · Fire Gate 16, Hillcrest Parkway
Fells Trail Run Club
Sunday at 10:00 AM + 1 more
Winchester · Fire Gate 16, Hillcrest Parkway
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
LABOR DAY WHITE PARTY @ TALL SHIP
Mon, Sep 7, 12:00 PM
Boston · The Tall Ship Boston
LABOR DAY WHITE PARTY @ TALL SHIP
Mon, Sep 7, 12:00 PM
Boston · The Tall Ship Boston
Going fast
BVS' Summer Biotech Community Celebration at Tech Square, Cambridge
Thursday at 4:00 PM
Cambridge · Tech Square Courtyard
Going fast
BVS' Summer Biotech Community Celebration at Tech Square, Cambridge
Thursday at 4:00 PM
Cambridge · Tech Square Courtyard
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
Annual YES Harbor Cruise
Thu, Jun 25, 6:00 PM
Boston · Massachusetts Bay Lines
Annual YES Harbor Cruise
Thu, Jun 25, 6:00 PM
Boston · Massachusetts Bay Lines
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Thursday at 6:00 PM + 13 more
Andover · 90 Harold Parker Rd
Sales end soon
Harold Parker Weekly Ride Series - Thursdays, 6pm roll
Thursday at 6:00 PM + 13 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
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
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
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
The 2nd Incredible Summer Boat Tour: Massport’s Strategy for Boston Harbor!
Fri, Jun 26, 1:30 PM
Cambridge · 100 Cambridgeside Pl
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

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