Community Events in Gloucester, MA

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

• Annual Pumpkin Sale at West Gloucester Trinitarian Congregational Church

  Nov 7 – Apr 22, 2027 · 3:00 PM

  West Gloucester Trinitarian Congregational Church, 488 Essex Ave, Gloucester, MA

  See tickets

• North Shore Renaissance Faire

  Sunday, November 8, 2026 · 9:00 AM

  Hammond Castle, 80 Hesperus Ave, Gloucester, MA

  $10

• Holiday Pop-up at North Shore Art Association

  Sunday, November 8, 2026 · 10:00 AM

  North Shore Arts Association, 11 Pirates Lane, Gloucester, MA

  See tickets

• Swing Dance at Gloucester

  Nov 8 – Apr 11, 2027 · 6:00 PM

  8 Washington Street, Gloucester, MA

  $15–$18

• Rocky Neck Art Colony Life Drawing Workshops

  Nov 9 – May 3, 2027 · 1:00 PM

  The Cultural Center at Rocky Neck, 6 Wonson Street, Gloucester, MA

  $20–$25

• Gloucester Gratis Days at Hammond Castle Museum

  Nov 8 – Mar 18, 2027 · 9:00 AM

  Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA

  Free

• Corporate Communications Meeting

  Tuesday, November 10, 2026 · 9:00 AM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Membership Drop-In Hours

  Nov 10 – Dec 22, 2026 · 10:00 AM

  Greater Cape Ann Chamber of Commerce, 24 Harbor Loop, Gloucester, MA

  Free

• Mah Jongg Meet Up

  Nov 10 – Nov 17, 2026 · 1:30 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Computer Basics

  Nov 10 – Nov 21, 2026 · Start times 10:00 AM – 3:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Chess Club

  Nov 10 – Nov 17, 2026 · 4:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• NSTC & NE First Robotics and STEM Workforce

  Tuesday, November 10, 2026 · 5:00 PM

  Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA

  $35–$50

• En Plein Air Sketch Classes with Sue Wheeler

  Nov 12 – Apr 8, 2027 · 1:00 PM

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

  $25

• Culture Splash Returns to Rocky Neck

  Nov 12 – Feb 11, 2027 · 4:00 PM

  Rocky Neck Cultural District, 51 Rocky Neck Restaurant, Gloucester, MA

  Free

• Gloucester History Exchange: Local History Discussion Group

  Thursday, November 12, 2026 · 5:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• The Strange Story of Maria Hallett with Richard Zapf

  Thursday, November 12, 2026 · 5:30 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• Spiritualism Tours by Candlelight

  Nov 12 – Apr 1, 2027 · 6:30 PM

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

  $27.50–$35

• Captain Elias Davis House Tour

  Nov 13 – Mar 26, 2027 · 2:00 PM

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

  Free

• Sound Healing in the Salt Cave

  Nov 13 – Dec 11, 2026 · 6:00 PM

  Revive Wellness 232 Main Street, Gloucester, MA, 232 Main St, MA

  $55

• Rockport Exchange Farmers Market

  Nov 14 – Mar 13, 2027 · 9:00 AM

  Harvey Park, MA

  See tickets

• AI's Promise and Peril: A Conversation

  Saturday, November 14, 2026 · 1:00 PM

  Gloucester City Hall, 9 Dale Ave., Gloucester, MA

  Free

• History of Cape Ann Rail

  Saturday, November 14, 2026 · 3:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Sold out

• Beauport Boutique's Annual Sip & Shop

  Sunday, November 15, 2026 · 2:00 PM

  Beauport Hotel Gloucester, 55 Commercial Street, Gloucester, MA

  See tickets

• Paint a Drippy Sky for Teens & Tweens

  Monday, November 16, 2026 · 3:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• Artful Conversations: Baptism by Anne Rearick

  Nov 19 – Dec 3, 2026 · Start times 12:30 PM – 1:30 PM

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

  $5–$25

• Sound Artist Office Hours

  Nov 12 – Nov 19, 2026 · 3:30 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Page To Screen Book Group: Hamnet

  Thursday, November 19, 2026 · 5:30 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• Third Thursday Music Therapy Show

  Thursday, November 19, 2026 · 7:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

  Genres: jazz/blues

• Deck the Halls at Hammond Castle Museum

  Nov 20 – Jan 3, 2027 · 9:00 AM

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

  See tickets

• Local History Sharing: A Year in the Life of John Hays Hammond Jr.

  Saturday, November 21, 2026 · 2:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• Karaoke with DJ Lou

  Friday, November 27, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Cape Ann Makers Market Holiday Sip n Shop

  Sunday, November 29, 2026 · 10:00 AM

  Cruiseport Gloucester, 6 Rowe Square, Gloucester, Massachusetts

  See tickets

• Wake Up Spirit Dance and Music

  Dec 6 – May 2, 2027 · 11:00 AM

  Floating Lotus, 169 Main Street, Gloucester, MA

  $10–$15

• Middle Street Walking Tour

  Saturday, December 12, 2026 · 11:00 AM

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

  Free

• Holidays & Wintertide

  Saturday, December 12, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Menorah Lighting and Chanukah Celebration

  Monday, December 14, 2026 · 4:00 PM

  Barletta Park, MA

  Free

• Navigating Health Care on Cape Ann Symposium

  Tuesday, April 13, 2027 · 1:30 PM

  Gloucester Meetinghouse, 50 Middle Street, Gloucester, MA

  Free

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