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Outdoor Events and Things to do in Gloucester, MA

Endicott College Homecoming & Reunion Weekend 2026
Fri, Sep 25, 12:00 AM
The Cove · Endicott College
Endicott College Homecoming & Reunion Weekend 2026
Fri, Sep 25, 12:00 AM
The Cove · Endicott College
The Salem Night Faire 2026
South Salem · Salem Pioneer Village
The Salem Night Faire 2026
South Salem · Salem Pioneer Village
Hawthorne Hotel's 2026 Halloween Ball: Phobia
Sat, Oct 24, 7:30 PM
Derby Wharf · Hawthorne Hotel
Hawthorne Hotel's 2026 Halloween Ball: Phobia
Sat, Oct 24, 7:30 PM
Derby Wharf · Hawthorne Hotel
Endicott College Football vs Eastern
Sat, Sep 5, 12:00 PM
The Cove · Hempstead Stadium, Endicott College
Endicott College Football vs Eastern
Sat, Sep 5, 12:00 PM
The Cove · Hempstead Stadium, Endicott College
Essex County Club
West Manchester · Essex County Club
Essex County Club
West Manchester · Essex County Club
Fight Night At The Fairgrounds
Sunday at 1:00 PM
Kinsman Corner · Topsfield Fairgrounds
Fight Night At The Fairgrounds
Sunday at 1:00 PM
Kinsman Corner · Topsfield Fairgrounds
12th Annual Halloween Gala
Thu, Oct 22, 6:30 PM
Massachusetts · Willowdale Estate
12th Annual Halloween Gala
Thu, Oct 22, 6:30 PM
Massachusetts · Willowdale Estate
The East Coast Throwdown in Witch City
Sun, Sep 6, 9:00 AM
The Point · 35 Congress St
The East Coast Throwdown in Witch City
Sun, Sep 6, 9:00 AM
The Point · 35 Congress St
Day with EC Dancers
Sat, Oct 24, 9:00 AM
The Cove · Endicott College Post Center
Day with EC Dancers
Sat, Oct 24, 9:00 AM
The Cove · Endicott College Post Center
Cast Off with the Canines: End-of-Summer Dog Cruise
Sat, Sep 5, 4:00 PM
South Salem · 23 Congress St
Cast Off with the Canines: End-of-Summer Dog Cruise
Sat, Sep 5, 4:00 PM
South Salem · 23 Congress St
2026 Oysterfest In The Port | Newburyport’s Premier Oyster Festival
Sat, Sep 26, 1:00 PM
Downtown · The Tannery Marketplace, Behind Building #5
2026 Oysterfest In The Port | Newburyport’s Premier Oyster Festival
Sat, Sep 26, 1:00 PM
Downtown · The Tannery Marketplace, Behind Building #5
Sip and Sculpt with FIT Ritual
Sunday at 8:00 AM
Downtown Gloucester · 65 Main St
Sip and Sculpt with FIT Ritual
Sunday at 8:00 AM
Downtown Gloucester · 65 Main St
Newburyport Chocolate Tour - 3 Oct 2026, 12-4 PM
Sat, Oct 3, 12:00 PM
Browns Square · First Religious Society Unitarian Universalist
Newburyport Chocolate Tour - 3 Oct 2026, 12-4 PM
Sat, Oct 3, 12:00 PM
Browns Square · First Religious Society Unitarian Universalist
Great Misery Island Birding and Nature Tour with Chris Leahy
Fri, Sep 18, 8:00 AM
Derby Wharf · Salem Ferry Dock
Great Misery Island Birding and Nature Tour with Chris Leahy
Fri, Sep 18, 8:00 AM
Derby Wharf · Salem Ferry Dock
Vino & Vinyasa
Wednesday at 6:00 PM
The Cove · Misselwood Events at Endicott College
Vino & Vinyasa
Wednesday at 6:00 PM
The Cove · Misselwood Events at Endicott College
Beer Garden - DECADES of ROCK Band! Summer 2026
Tomorrow at 5:00 PM
Danvers Center · Glen Magna Farms
Beer Garden - DECADES of ROCK Band! Summer 2026
Tomorrow at 5:00 PM
Danvers Center · Glen Magna Farms
8TH ANNUAL CRUISE FOR LEUKEMIA
Sun, Sep 13, 4:00 PM
Browns Square · 54 Merrimac St
8TH ANNUAL CRUISE FOR LEUKEMIA
Sun, Sep 13, 4:00 PM
Browns Square · 54 Merrimac St
School to Sea: Adult Cruise
Thursday at 5:00 PM
Derby Wharf · Mahi Harbor Cruises & Private Events
School to Sea: Adult Cruise
Thursday at 5:00 PM
Derby Wharf · Mahi Harbor Cruises & Private Events
Endicott Women's Lacrosse Prospect Day
Sun, Sep 20, 12:30 PM
The Cove · Hempstead Stadium, Endicott College
Endicott Women's Lacrosse Prospect Day
Sun, Sep 20, 12:30 PM
The Cove · Hempstead Stadium, Endicott College
Lanterns in the Woods (Previously Lanterns in the Village)
Fri, Oct 9, 6:30 PM
South Salem · Salem High School
Lanterns in the Woods (Previously Lanterns in the Village)
Fri, Oct 9, 6:30 PM
South Salem · Salem High School

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