Arts & Entertainment in Gloucester, MA

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

• HOMECOMING Drag Show starring Laila McQueen

  Saturday, November 7, 2026 · 8:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Daily Guided & Self-Guided Tour of Hammond Castle

  Nov 8 – Mar 18, 2027 · 9:00 AM

  Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA

  $4–$20

• 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

• 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

• Lyceum Meeting

  Thursday, November 12, 2026 · 5:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Spiritualism Tours by Candlelight

  Nov 12 – Jan 28, 2027 · 6:30 PM

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

  $27.50–$35

• Contra Dance

  Saturday, November 14, 2026 · 7:00 PM

  MAGMA, 11 Pleasant St., Gloucester, MA

  $15–$25

• Artful Conversations: Baptism by Anne Rearick

  Nov 19 – Dec 3, 2026 · 12:30 PM

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

  $5–$25

• 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

• A Night of Comedy with Jay Larson

  Thursday, November 19, 2026 · 7:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Greenheads Film Screening

  Friday, November 20, 2026 · 3:00 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

• 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

• 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

• 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

• Holidays & Wintertide

  Saturday, December 12, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Tease the Season Burlesque Show

  Sunday, December 13, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Annual Live Christmas Pageant

  Sunday, December 20, 2026 · 5:00 PM

  Dock Square, MA

  Free

• 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

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