63 Rogers Street, Gloucester, MA, United States, Massachusetts 01930
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LABOR DAY IN GLOUCESTER
Labor Day Weekend Eventsin Gloucester 2026
Sep 5–7, 2026
19 ways to make the long weekend count.
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Weekend spotlight
19 events in Gloucester, All events
THE WEEKEND, DAY BY DAY
Find your day
Every event in Gloucester, grouped by the day it happens.
Weekend kickoff
3 events
Friday Sunset Session with Stephanie Rosa - Live Music...On the Water.
75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
Saturday, September 5
8 events
Neon 90s at Blue Collar Lobster
Blue Collar Lobster Co.
Sunset, Boat Parade, Yacht Rock at our Sun Deck with DJ Lou
75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
Labor Day Fireworks Cruise
Central Gloucester
Saturday, September 5th, Sunset Sessions: Summer's Grand Finale
· USD 55 to 429
Beauport Hotel Gloucester
2026 Boat Parade of Lights - Gloucester
Central Gloucester
Barry Gourdreau's Engine Room
The Cut Live
Show 2 more
DJ SKULLY Saturday
The Cut Live
Sunday, September 6
6 events
Parade of Sail
Beauport, the Sleeper-McCann House
Gloucester Schooner Festival
Gloucester Schooner Festival
Fall Time Centerpieces Course
153 Main Street Gloucester MA 01930
Sunday - Labor Day Weekend live Music with Groove Therapy
75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
Labor Day Monday
1 event
Labor Day: Line's End featuring Millie Manning at BCL!
Blue Collar Lobster Co.
Best Labor Day Parties, Concerts, Festivals & Things To Do in Gloucester
Labor Day weekend in Gloucester fills itself in fast, which is more or less the point. Parades and festivals take the daylight hours, parties and concerts run late, and live music is rarely more than a short walk away. Bringing the kids changes the math a little, and a food festival or an afternoon outdoors usually wins that argument. If the whole goal is doing as little as possible, a quiet weekend getaway counts too. See what's happening around Gloucester this Labor Day 2026 and book your tickets while there's still room.
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More to do around Gloucester
More Labor Day events around Gloucester
THE DECK | PARROT HEAD PARTY (NEW DATE!)
179 Bridge Rd, Salisbury, MA, United States, Massachusetts
Souped Up Food Truck
115 Oak Hill Rd, Harvard, MA, United States, Massachusetts 01451