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Charity & causes Events and Things to do in Gloucester, MA this weekend

Looking for things to do in Gloucester this weekend? Explore our real-time listings for the best concerts, nightlife, and food and drink experiences. From seasonal festivals and comedy shows to free activities, find your next plan with our constantly updated feed of Gloucester's most popular events.

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Things to do around Gloucester

Trends in Gloucester

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Frequently asked questions about Gloucester

What are the best events to attend this weekend in Gloucester?

The best events to attend this weekend in Gloucester include concerts, nightlife experiences, seasonal events, food and drink tastings, and live entertainment happening across the city. According to Eventbrite, some of the best events this weekend include:
  • 10th Annual - 2026 We Are WINARC Walk, Run, or Roll Fundraiser
  • A Night Out with New Friends: Revere | Giving Back Edition
  • Fourth Fest
  • Kentucky Derby Oaks Day Purple Gala!

    • Which events are currently trending in Gloucester?

    Trending weekend events in Gloucester often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Gloucester are:
  • north shore happenings
  • kids events today
  • comedy
  • speed dating

    • Which events are coming up in Gloucester this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Gloucester, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Art-Making for Humanity (Boston)
  • Bid for Brighter Futures - Charity Dinner Dance
  • Crazy Bingo for the Jimmy Fund
  • Fine Line 40th Anniversary MIT DKE Benefit

    • Are there free things to do in Gloucester this weekend?

    Yes — there are often free things to do in Gloucester this weekend, including live music, cultural events, seasonal activities, and community gatherings. Many events on Eventbrite are free or offer free entry options. These are some free events happening in Gloucester this weekend:
  • Free Events this weekend