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.

• Painting Light with Water Based Oils

  Thursday, September 24, 2026 · 2:00 PM

  3 Centennial Ave., 3 Centennial Ave., Gloucester, MA

  See tickets

• 39th Annual Fundraising Auction: Together, Let’s Glow

  Thursday, September 24, 2026 · 5:00 PM

  Cruiseport Gloucester, 6 Rowe Square, MA

  $100–$900

• TownGreen Emergency Preparedness Workshop

  Thursday, September 24, 2026 · 5:30 PM

  Sawyer Free Library, Gloucester, 2 Dale Avenue, MA

  See tickets

• Reset your Nervous System – Lose Weight Workshop

  Thursday, September 24, 2026 · 6:00 PM

  232 Main St Gloucester, 232 Main St, MA

  $49

• Olana: Frederic Church’s Vision of Art & Landscape

  Thursday, September 24, 2026 · 6:00 PM

  Castle Hill on the Crane Estate, Argilla Road 290, Ipswich, M, MA

  $28–$35

• The Open Door: TownGreen Neighborhood Resiliency Project

  Friday, September 25, 2026 · 10:30 AM

  The Open Door, 28 Emerson Avenue, Gloucester, MA

  See tickets

• Captain Elias Davis House Tour

  Sep 25 – Mar 19, 2027 · 2:00 PM

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

  Free

• Public Sail on a Historic Schooner

  Friday, September 25, 2026 · 4:00 PM

  Schooner Adventure, 23 Harbor Loop | Schooner Adventure, Gloucester, MA

  $60

• Daily Guided and Self-Guided Tour of Hammond Castle Museum

  Sep 26 – Mar 14, 2027 · 9:00 AM

  Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA

  $4–$20

• 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

• Rockport Autumn Market Pop-Up

  Saturday, September 26, 2026 · 2:00 PM

  1 Twin Light Circle, Rockport, MA, 1 Twin Light Circle, MA

  See tickets

• Manhattan Short Film Festival

  Sunday, September 27, 2026 · 2:00 PM

  Shalin Liu Performance Center, 37 Main Street, Rockport, MA

  $10

• 1926: A Year in the Life of Hammond and His Castle

  Wednesday, September 30, 2026 · 5:30 PM

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

  $15

• Preserving Scenic Beauty in Eliot’s Museum of Landscapes

  Thursday, October 1, 2026 · 6:00 PM

  Castle Hill on the Crane Estate, Argilla Road 290, Ipswich, M, MA

  $28–$35

• Mollydooker Wine Pairing Dinner

  Thursday, October 1, 2026 · 6:30 PM

  Beauport Hotel Gloucester, 55 Commercial Street, MA

  $120

• En Plein Air Sketch Classes with Sue Wheeler

  Oct 3 – Oct 8, 2026 · Start times 8:00 AM – 1:00 PM

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

  $25

• Beauport Cruiselines Oktoberfest Cruise

  Saturday, October 3, 2026 · 1:00 PM

  Beauport Cruiselines, 6 Rowe Square, Gloucester, MA

  $69

• Toni Nagy Somatic Movement Workshop

  Saturday, October 3, 2026 · 4:00 PM

  MAGMA, 11 Pleasant St., Gloucester, MA

  $35–$45

• CAM Studio Art: Design and Print the Folly Cove Way

  Oct 7 – Nov 4, 2026 · 1:00 PM

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

  $100–$160

• Sound Healing in the Salt Cave

  Oct 9 – Dec 11, 2026 · 6:00 PM

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

  $55

• Halloween Samhain Book Reading at Apothecary Suil Crow

  Friday, October 9, 2026 · 6:00 PM

  Apothecary Suil Crow, 153 Main Street, Gloucester, MA

  Free

• Family Programs: Second Saturdays

  Oct 10 – Dec 12, 2026 · 10:00 AM

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

  Free

• Beauport Cruiselines Lobster Lunch Cruises

  Wednesday, October 14, 2026 · 11:00 AM

  Beauport Cruiselines, 6 Rowe Square, Gloucester, MA

  $92

• Third Thursday Music Therapy Show

  Oct 15 – Nov 19, 2026 · 7:00 PM

  The Cut, 177 Main Street, MA

  Free

  Genres: jazz/blues

• Rockport Harvest Fest

  Saturday, October 17, 2026 · 11:00 AM

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

  Free

• 41st Annual Essex Clamfest and Arts Crafts Festival

  Saturday, October 24, 2026 · 11:00 AM

  Shepard Memorial Park, 24 Martin Street, Essex, MA

  $15

• CAM Talk: From Clay to Bronze, The Making of the Seated Cat

  Saturday, October 24, 2026 · 2:00 PM

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

  $5–$30

• Trick-or-Treat at the Castle

  Wednesday, October 28, 2026 · 4:00 PM

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

  $10

• Hotel Transylvania

  Saturday, October 31, 2026 · 11:00 AM

  Shalin Liu Performance Center, 37 Main Street, Rockport, MA

  Free

• Beauport Hotel Halloween Soirée

  Saturday, October 31, 2026 · 8:00 PM

  Beauport Hotel, 55 Commercial Street, Gloucester, MA

  $70

• Renaissance Faire at Hammond Castle

  Nov 7 – Nov 8, 2026 · 9:00 AM

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

  $35

• 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

• 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

• Middle Street Walking Tour

  Saturday, December 12, 2026 · 11:00 AM

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

  Free

• Menorah Lighting and Chanukah Celebration

  Monday, December 14, 2026 · 4:00 PM

  Barletta Park, MA

  Free

• MLK Day Celebration

  Wednesday, January 20, 2027 · 2:00 PM

  Gloucester Unitarian Universalist Church, 10 Church Street, Gloucester, MA

  Free

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