18 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Dalloway: First Love (Thursday evenings) Thu 13 Aug 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Dalloway: First Love (Friday evenings) Fri 14 Aug 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Dalloway: First Love (Saturday evenings) Sat 15 Aug 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Dalloway: First Love (Sunday matinees) Sun 16 Aug 2026, 2:00 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Dalloway: First Love (Wednesday evenings) Wed 19 Aug 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Sunset Sessions: Summer's Grand Finale Sat 5 Sep 2026, 7:00 PM — Live music Birdseye Rooftop, Beauport Hotel Gloucester · 55 Commercial St, Gloucester, MA 01930 · $55.20 · 21+
SRP live at Decklyns Sat 5 Sep 2026, 8:00 PM — Live music Decklyn's · 31 Harbor Loop, Gloucester, MA 01930
Sunday, September 6th, Live Music at Birdseye Rooftop Sun 6 Sep 2026, 6:00 PM — Live music Beauport Hotel Gloucester · 55 Commercial Street, Gloucester, MA 01930
Moon Man Walk (Thursday evenings) Thu 10 Sep 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Moon Man Walk (Friday evenings) Fri 11 Sep 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Moon Man Walk (Saturday evenings) Sat 12 Sep 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Inclusive Surf Fest Gloucester by Gnome Surf Sun 13 Sep 2026, 1:00 PM — Festival Good Harbor Beach · 99 Thatcher Road, Gloucester, MA 01930
Moon Man Walk (Sunday matinees) Sun 13 Sep 2026, 2:00 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Moon Man Walk (Wednesday evenings) Wed 16 Sep 2026, 7:30 PM — Theater Natti-Willsky Performance Center, Gloucester Stage Company · 267 E Main St, Gloucester, MA 01930
Little River Reverb - A Summer Concert to Benefit ACTION, INC. Sat 19 Sep 2026, 4:00 PM — Theater 7 Crafts Rd · 7 Crafts Road, Gloucester, MA 01930
GIRLS NIGHT OUT LIVE -LAS VEGAS TAKEOVER -GLOUCESTER,MA Sat 26 Sep 2026, 8:00 PM — Theater American Legion Post 3 · 8 Washington Street, Gloucester, MA 01930
Gloucester, MA the Absolute Men Takeover Tour!! Sat 26 Sep 2026, 8:00 PM — Comedy American Legion Post 3 · 8 Washington Street, Gloucester, MA 01930
Next Wave Event Wed 14 Oct 2026, 6:00 PM — Live music Beauport Cruiselines · 6 Rowe Square #3057, Gloucester, MA 01930
Listings are seeded from venue and organiser calendars. See them on the map.