Chill Things to Do in Gloucester, MA

Discover chill things to do in Gloucester, MA on VibeHawk: theatre, galleries, markets and yoga. 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

• Opening Reception: The Great Marsh Starts Here

  Saturday, November 7, 2026 · 4:00 PM

  Cultural Center at Rocky Neck, 6 Wonson Street Gloucester, Massachusetts

  Free

• Bad Books by Sharyn Rothstein

  Nov 7 – May 6, 2027 · 7:30 PM

  Natti-Willsky Performance Center, 267 East Main St, Gloucester, MA

  $18–$74

• 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

• The Great Marsh Starts Here

  Nov 8 – Dec 20, 2026 · 12:00 PM

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

  Free

• Cape Ann Shakespeare Troupe: Laugh Out Loud

  Nov 7 – Nov 15, 2026 · Start times 3:00 PM – 7:30 PM

  The Natti-Willsky Performance Center, 267 East Main Street, Gloucester, MA

  $38

• 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

• Computer Basics

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

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Yoga At The Castle

  Nov 11 – Dec 30, 2026 · 7:30 AM

  Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA

  $75–$90

• Weekly Session: Celtic Music

  Nov 11 – Apr 7, 2027 · 6:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

  Genres: country/folk

• Artful Conversations: Sierra and Hawk Henries

  Nov 12 – Mar 18, 2027 · 12:30 PM

  Cape Ann Museum, 27 Pleasant St, Gloucester, MA

  $5–$25

• Artful Conversations: John Sloan's Scavenger Rocks

  Thursday, November 12, 2026 · 12:30 PM

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

  $5–$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

• Thursday Acoustic Corner

  Nov 12 – May 6, 2027 · 7:00 PM

  Minglewood Harborside, MA

  Free

  Genres: country/folk

• Chair Yoga

  Nov 13 – Nov 20, 2026 · 10:45 AM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• 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

• We Were There": Gloucester Women of the Revolution Film Screening

  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

• Greenheads Film Screening

  Friday, November 20, 2026 · 3:00 PM

  Sawyer Free Library, 2 Dale Avenue, 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

• The Psychedelic Cinema Orchestra

  Saturday, November 21, 2026 · 7:30 PM

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

  $5–$25

• Cape Ann Makers Market Holiday Sip n Shop

  Sunday, November 29, 2026 · 10:00 AM

  Cruiseport Gloucester, 6 Rowe Square, Gloucester, Massachusetts

  See tickets

• Gloucester Film Release: The Networks: Art + Fishing + Community

  Sunday, November 29, 2026 · 6:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Fiona Brehony Explores Gloucester Harbor, Whale Song, and the Living Memory of Water

  Thursday, December 3, 2026 · 5:00 PM

  Rocky Neck, MA

  Free

• Chakra Yoga

  Dec 3 – Feb 4, 2027 · 7:15 PM

  Revive Wellness in the Main Hall, 232 Main St., Gloucester, MA

  $40

• Over by Jessica Algard

  Dec 4 – Dec 6, 2026 · 7:30 PM

  Natti-Willsky Performance Center: Home of Gloucester Stage Company, 267 East Main St., Gloucester, MA

  $46–$56

• Wake Up Spirit Dance and Music

  Dec 6 – May 2, 2027 · 11:00 AM

  Floating Lotus, 169 Main Street, Gloucester, MA

  $10–$15

• Artful Conversations: Regionalism and Modernism

  Dec 10 – Dec 17, 2026 · 12:30 PM

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

  $5–$25

• 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

• Will Evans with Steve Rondo

  Saturday, January 30, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: country/folk

• Gabe Dixon

  Friday, February 12, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: country/folk

• Cape Ann Shakespeare Troupe presents Richard III

  Apr 9 – Apr 11, 2027 · 7:30 PM

  Natti-Willsky Performance Center: Home of Gloucester Stage Company, MA

  $33

• 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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