Things to Do in Gloucester, MA

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

• Holiday Pop-up at North Shore Art Association

  Nov 7 – Nov 8, 2026 · 10:00 AM

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

  See tickets

• Computer Basics

  Nov 7 – Nov 21, 2026 · Start times 10:00 AM – 3:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• Fall into Reading & the Arts Scavenger Hunt Drop-In

  Saturday, November 7, 2026 · 11:00 AM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• From the Deep 2026: A Fall Downtown Gloucester Arts Party

  Saturday, November 7, 2026 · 11:00 AM

  Downtown Gloucester, MA

  Free

• Local Colors 37th Artist Demonstrations

  Saturday, November 7, 2026 · 11:00 AM

  121 Main St, Gloucester, MA

  Free

• Paper Fun, Coloring, and Cut-outs with Betty Wiberg

  Saturday, November 7, 2026 · 11:30 AM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  Free

• The Great Marsh Starts Here

  Nov 7 – Dec 20, 2026 · 12:00 PM

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

  Free

• Dungeons & Dragons

  Saturday, November 7, 2026 · 12:30 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See 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

• Sunset Sessions at Birdseye Rooftop

  Nov 7 – Jan 30, 2027 · 7:00 PM

  Birdseye Rooftop at Beauport Hotel, 55 Commercial Street, Gloucester, MA

  $30–$300

  Genres: electronic

• Bad Books by Sharyn Rothstein

  Nov 7 – May 5, 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

• Orchid Reed

  Saturday, November 7, 2026 · 9:00 PM

  Minglewood Harborside, MA

  Free

  Genres: pop, rock

• NFL Sunday Ticket Watch Party

  Nov 8 – Apr 25, 2027 · All day

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• North Shore Renaissance Faire

  Sunday, November 8, 2026 · 9:00 AM

  Hammond Castle, 80 Hesperus Ave, Gloucester, MA

  $10

• 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

• Birdseye Rooftop Live Music Access

  Nov 8 – Feb 4, 2027 · 6:00 PM

  Birdseye Rooftop at Beauport Hotel, 55 Commercial Street, Gloucester, MA

  $20

• 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

• Cape Ann Youth Chorus

  Monday, November 9, 2026 · 5:00 PM

  Sawyer Free Library, 2 Dale Avenue, Gloucester, MA

  See tickets

• 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

• 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

• Beauport Sessions: Live Music

  Nov 10 – May 4, 2027 · 6:00 PM

  Beauport Hotel, 55 Commercial Street, 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

• 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

• Thursday Acoustic Corner

  Nov 12 – Apr 29, 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

• The Joshua Tree - U2 Tribute

  Friday, November 13, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $19.50

• Local 28 Grateful Dead Tribute

  Friday, November 13, 2026 · 9:00 PM

  Minglewood Harborside, MA

  Free

  Genres: rock

• 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

• Contra Dance

  Saturday, November 14, 2026 · 7:00 PM

  MAGMA, 11 Pleasant St., Gloucester, MA

  $15–$25

• Delta Generators with Julie Rhodes

  Saturday, November 14, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $19.50–$39.50

• Spittin Vinnies

  Saturday, November 14, 2026 · 9:00 PM

  Minglewood Harborside, MA

  Free

  Genres: rock, pop

• 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

• 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

  Nov 19 – Apr 15, 2027 · 7:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

  Genres: jazz/blues

• A Night of Comedy with Jay Larson

  Thursday, November 19, 2026 · 7:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• 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

• Old Hickory Blvd

  Friday, November 20, 2026 · 9:00 PM

  Minglewood Harborside, MA

  Free

• 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

• BT ALC Big Band

  Saturday, November 21, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $19.50

• Karaoke with DJ Lou

  Friday, November 27, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $5

• Funbucket

  Friday, November 27, 2026 · 9:00 PM

  Minglewood Harborside, MA

  Free

• Bim Skala Bim w/ Special Guest The Chip Rockers

  Saturday, November 28, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $26.45–$41.45

  Genres: hip-hop/r&b

• 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

• Little Lies - Tribute to Fleetwood Mac

  Friday, December 4, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $31.45

• Happy Holidays Half MerryThon & 5K Race

  Saturday, December 5, 2026 · 7:00 PM

  99 Thatcher Road, Gloucester, MA

  $10–$122.08

• Phil Vassar with Annie Brobst

  Saturday, December 5, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b, country/folk

• 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

• John Cafferty and The Beaver Brown Band

  Friday, December 11, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: rock

• 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

• Once Upon a Winter: Tales of Wonder Through a Child's Eyes

  Sunday, December 13, 2026 · 4:00 PM

  Gloucester Unitarian Universalist Church, 10 Church 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

• Menorah Lighting and Chanukah Celebration

  Monday, December 14, 2026 · 4:00 PM

  Barletta Park, MA

  Free

• BrassFed Nation's Holiday Bash

  Friday, December 18, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b, jazz/blues

• Annual Live Christmas Pageant

  Sunday, December 20, 2026 · 5:00 PM

  Dock Square, MA

  Free

• Legend of Ozzy

  Saturday, January 9, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• The Beautiful Losers — A Tribute to Bob Seger & The Silver Bullet Band

  Saturday, January 16, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: rock

• Albert Lee with Special Guests The Cryers

  Tuesday, January 19, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Will Evans with Steve Rondo

  Saturday, January 30, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: country/folk

• Dueling Pianos

  Friday, February 5, 2027 · All day

  The Cut, 177 Main Street, Gloucester, MA

  $14.50

• Jambalaya Horns Mardi Gras Party

  Saturday, February 6, 2027 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b

• 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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