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.

• Macbeth

  Saturday, October 17, 2026 · 1:00 PM

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

  $30

  Genres: classical

• Celtic Seisiún at The Cut

  Sep 23 – Mar 17, 2027 · 6:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

  Genres: country/folk

• Moon Man Walk

  Sep 23 – Sep 29, 2026 · 7:30 PM

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

  $18–$74

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

  Sep 24 – Mar 14, 2027 · 9:00 AM

  Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA

  $4–$20

• Artful Conversations: Sierra 'Autumn' Henries & Hawk Henries

  Thursday, September 24, 2026 · 12:30 PM

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

  $25

• 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

• Spiritualism Tours by Candlelight at Hammond Castle Museum

  Sep 24 – Oct 29, 2026 · 6:00 PM

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

  $27.50–$35

• 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

• Live Music with Peter Tentindo

  Friday, September 25, 2026 · 7:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

• Trey Hensley

  Friday, September 25, 2026 · 7:30 PM

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

  $23

• 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

• Manship Artist Residency: David Hockney

  Saturday, September 26, 2026 · 2:00 PM

  Sawyer Free Library, 2 Dale Ave., Gloucester, MA

  Free

• Good Harbor Beach Full Moon Dance & Ground

  Saturday, September 26, 2026 · 6:30 PM

  1 Salt Island Rd, Gloucester, MA

  $20

• Ana Popovic with Danielle Miraglia

  Saturday, September 26, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

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

• DJ Vito & Friends Night

  Saturday, September 26, 2026 · 9:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

  Genres: electronic

• Manhattan Short Film Festival

  Sep 27 – Oct 4, 2026 · Start times 2:00 PM – 7:00 PM

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

  $10

• The Crystal

  Sunday, September 27, 2026 · 4:00 PM

  MAGMA, 11 Pleasant St., Gloucester, MA

  $10–$20

• 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

• Ruthie Foster

  Thursday, October 1, 2026 · 7:30 PM

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

  $39

  Genres: hip-hop/r&b

• Flamenkora

  Thursday, October 1, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Cape Ann Plein Air

  Saturday, October 3, 2026 · All day

  Cape Ann, MA

  See tickets

• 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

• Five For Fighting

  Saturday, October 3, 2026 · 7:30 PM

  37 Main St , Rockport, Massachusetts

  $175–$218.22

  Genres: pop, country/folk

• Dueling Pianos

  Saturday, October 3, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• K-Pop Dance Battle: Family Dance Party

  Sunday, October 4, 2026 · 1:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Met Live In HD: Cosi Fan Tutte

  Sunday, October 4, 2026 · 1:00 PM

  37 Main St , Rockport, Massachusetts

  $55–$85.10

  Genres: classical

• 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

• Strictly Sinatra

  Thursday, October 8, 2026 · 7:30 PM

  37 Main St , Rockport, Massachusetts

  $87.40

  Genres: jazz/blues, pop

• Nervous Guys | G Gordon Gritty | The Chip Rockers | Beware the Dangers of a Ghost Scorpion

  Thursday, October 8, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: rock, hip-hop/r&b

• 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

• Cape Ann Plein Air Gala & Art Sale

  Friday, October 9, 2026 · 6:00 PM

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

  $100

• Halloween Samhain Book Reading at Apothecary Suil Crow

  Friday, October 9, 2026 · 6:00 PM

  Apothecary Suil Crow, 153 Main Street, Gloucester, MA

  Free

• Stacey Kent

  Friday, October 9, 2026 · 7:30 PM

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

  $38

  Genres: jazz/blues

• Grunge Fest: Alice in Chains & Stone Temple Pilots Tribute

  Friday, October 9, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: rock

• Family Programs: Second Saturdays

  Oct 10 – Dec 12, 2026 · 10:00 AM

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

  Free

• Chanticleer

  Saturday, October 10, 2026 · 7:30 PM

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

  $58

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

• Abigail Rose & Melanie MacLaren

  Sunday, October 11, 2026 · 5:00 PM

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

  $21

  Genres: country/folk

• Jimmy Tingle: The ‘Radical’ Middle

  Sunday, October 11, 2026 · 6:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• 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 – Dec 17, 2026 · 7:00 PM

  The Cut, 177 Main Street, MA

  Free

  Genres: jazz/blues

• Third Thursday Therapy with Big O'l Dirty Bucket

  Oct 15 – Mar 18, 2027 · 7:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  Free

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

• Neko Case

  Friday, October 16, 2026 · 7:30 PM

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

  $96

• Reckoners with Kevin James Graham

  Friday, October 16, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b

• Rockport Harvest Fest

  Saturday, October 17, 2026 · 11:00 AM

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

  Free

• Chelsea Berry

  Saturday, October 17, 2026 · 7:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: rock, country/folk

• Cheyenne Jackson

  Sunday, October 18, 2026 · 5:00 PM

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

  $68

• Jerron Paxton and Dennis Lichtman

  Wednesday, October 21, 2026 · 7:00 PM

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

  Free

  Genres: jazz/blues

• Magic Hunks

  Thursday, October 22, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• 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

• Josh Ritter

  Wednesday, October 28, 2026 · 7:30 PM

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

  $58

  Genres: country/folk

• East Nash Grass

  Friday, October 30, 2026 · 7:30 PM

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

  $33

• Safety 80's: 21+ Halloween Late Show

  Friday, October 30, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Hotel Transylvania

  Saturday, October 31, 2026 · 11:00 AM

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

  Free

• SAFETY 80’S – Early ALL AGES Halloween Show

  Saturday, October 31, 2026 · 1:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  $12.25

• Beauport Hotel Halloween Soirée

  Saturday, October 31, 2026 · 8:00 PM

  Beauport Hotel, 55 Commercial Street, Gloucester, MA

  $70

• Booty Vortex Halloween Show

  Saturday, October 31, 2026 · 8:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b

• Santiago Cañón-Valencia, cello

  Sunday, November 1, 2026 · 3:00 PM

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

  $41

• JazzReach's METTA QUINTET

  Monday, November 2, 2026 · 7:00 PM

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

  Free

  Genres: jazz/blues

• Artful Conversations: John Sloan’s Scavenger Rocks

  Nov 5 – Nov 12, 2026 · 12:30 PM

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

  $5–$25

• Renaissance Faire at Hammond Castle

  Nov 7 – Nov 8, 2026 · 9:00 AM

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

  $35

• Homecoming Drag Show starring Laila McQueen

  Saturday, November 7, 2026 · 8:30 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• The Joshua Tree: A Tribute to U2

  Friday, November 13, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• Delta Generators with Julie Rhodes

  Saturday, November 14, 2026 · 8:00 PM

  The Cut, 177 Main Street, 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

• BT ALC Big Band

  Saturday, November 21, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

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

• Bim Skala Bim w/ The Chip Rockers

  Saturday, November 28, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

  Genres: hip-hop/r&b

• Chris Isaak

  Monday, November 30, 2026 · All day

  37 Main St, Rockport, MA, 1966, MA

  $253

• Little Lies: A Tribute to Fleetwood Mac

  Friday, December 4, 2026 · 8:00 PM

  The Cut, 177 Main Street, Gloucester, MA

  See tickets

• 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

• 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

• Menorah Lighting and Chanukah Celebration

  Monday, December 14, 2026 · 4:00 PM

  Barletta Park, MA

  Free

• Annual Live Christmas Pageant

  Sunday, December 20, 2026 · 5:00 PM

  Dock Square, MA

  Free

• Painted Dreams: Live Music, Film & Fine Art

  Monday, January 18, 2027 · 6:00 PM

  MAGMA, 11 Pleasant St., Gloucester, MA

  $25

• MLK Day Celebration

  Wednesday, January 20, 2027 · 2:00 PM

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

  Free

• Discover Saturdays at Cape Ann Museum

  Sunday, January 24, 2027 · 10:00 AM

  Cape Ann Museum Green, MA

  Free

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