Family Events in Gloucester, MA

Discover family events in Gloucester, MA on VibeHawk. Browse upcoming events with dates, venues, and ticket prices, then tap any listing for details and tickets.

• Gloucester Community Safety Day

  Saturday, September 26, 2026 · 10:00 AM

  Gloucester Harbor Loop, 1 Harbor Loop, MA

  See tickets

• Choate Island Day

  Saturday, September 26, 2026 · 10:00 AM

  The Crane Estate, 310 Argilla Road, Ipswich, MA

  $35–$50

• Second Saturdays: Family Programs

  Oct 10 – Dec 12, 2026 · 10:00 AM

  Cape Ann Museum Downtown Campus, 27 Pleasant Street, Gloucester, MA

  See tickets

• Beauport Cruiselines Lobster Lunch Cruises

  Wednesday, October 14, 2026 · 11:00 AM

  Beauport Cruiselines, 6 Rowe Square, Gloucester, MA

  $92

• Rockport Harvest Fest

  Saturday, October 17, 2026 · 11:00 AM

  4 High Street, 4 High Street, Rockport, Rockport, MA

  Free

• Trick-or-Treat at the Castle

  Wednesday, October 28, 2026 · 4:00 PM

  Hammond Castle Museum, 80 Hesperus Ave., Gloucester, MA

  $10

• Renaissance Faire at Hammond Castle

  Nov 7 – Nov 8, 2026 · 9:00 AM

  Hammond Castle Museum, 80 Hesperus Ave., Gloucester, MA

  $35

• Santa Arrives at T-Wharf by Boat

  Sunday, December 6, 2026 · 1:00 PM

  T-Wharf on Rockport Harbor, MA

  Free

• Dock Square Tree Lighting Ceremony

  Sunday, December 6, 2026 · 4:00 PM

  Dock Square, MA

  Free

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