Skip to content
  • Weddings
  • Group Tours
  • Plan Your Visit
    • Travel Info
    • Transportation
    • FAQs
    • Summer
    • Travel Info
    • Transportation
    • FAQs
    • Summer
  • Things to do
    • Beaches and Outdoors
    • On the Water
    • Arts & Culture
    • Museums & Attractions
    • Historic Sites & Landmarks
    • Festivals
    • View all Things to Do
    • Beaches and Outdoors
    • On the Water
    • Arts & Culture
    • Museums & Attractions
    • Historic Sites & Landmarks
    • Festivals
    • View all Things to Do
  • Dine
    • Restaurants & Bars
    • Sweets & Treats
    • View All Dining
    • Restaurants & Bars
    • Sweets & Treats
    • View All Dining
  • Shop
    • Clothing & Accessories
    • Markets & Bakeries
    • Gifts & Souvenirs
    • View All Shops
    • Clothing & Accessories
    • Markets & Bakeries
    • Gifts & Souvenirs
    • View All Shops
  • Stay
  • Events
    • Calendar
    • Festivals
    • Culture Splash
    • Calendar
    • Festivals
    • Culture Splash
  • Neighborhoods
    • Downtown
    • East Gloucester
    • Dogtown, Annisquam, Lanesville
    • Magnolia
    • West Gloucester
    • Downtown
    • East Gloucester
    • Dogtown, Annisquam, Lanesville
    • Magnolia
    • West Gloucester
  • Blog
Get the Guide
12 events found.

Events

Events Search and Views Navigation

Event Views Navigation

  • List
  • Month
  • Day
  • Photo
Today
  • September 2026

  • Fri 4

    Sunset Sessions at the Birdseye Rooftop

    September 4 @ 7:00 pm - 10:00 pm Sunset Sessions at the Birdseye Rooftop
    Beauport Hotel 55 Commercial Street, Gloucester, MA, United States

    Enjoy the weekend in style at Sunset Sessions. An evening of vibrant energy, coastal glamour, and unforgettable harbor front views at Beauport Hotel’s Birdseye Rooftop. Join us during our 10th year by the sea, every Friday and Saturday evening for a lively celebration featuring DJ entertainment from The 617 Event Group. Dance as the sun […]

    $30
  • Fri 4

    Mighty Mystic with Double Tiger

    September 4 @ 8:00 pm - 11:00 pm
    The Cut 177 Main Street, Gloucester, MA, United States

    Mighty Mystic is considered as one of the leaders in the international reggae scene and is a box office draw at venues and a staple at festivals. The Jamaican born […]

  • Sat 5

    En Plein Air Sketch Classes with Sue Wheeler

    September 5 @ 9:30 am - 11:30 am En Plein Air Sketch Classes with Sue Wheeler
    Hammond Castle Museum 80 Hesperus Ave., Gloucester, MA, United States

    From stick figure doodlers to first-rate talents, join us for a seaside, En Plein Air sketch class with Sue Wheeler of Arts Abound in Magnolia. All skill levels are welcome! […]

    $25.00
  • Sat 5

    Street Stories with Phil Storey 2026

    September 5 @ 10:00 am Street Stories with Phil Storey 2026
    80 Main Antiques & Ephemera 80 Main Street, Gloucester, MA, United States

    Join noted raconteur Phil Storey for this "fun filled" Phil Facts about Gloucester's deep literary past! Phil Storey is a local local historian, noted raconteur, and master storyteller. He developed […]

  • Sat 5

    Avery, Gottlieb & Rothko: By the Sea

    September 5 @ 10:00 am - 5:00 pm Avery, Gottlieb & Rothko: By the Sea
    Cape Ann Museum Downtown Campus 27 Pleasant Street, Gloucester, MA, United States

    “Avery, Gottlieb & Rothko: By the Sea” explores the artistic bond between three pivotal 20th century American artists—Milton Avery (1885–1965), Adolph Gottlieb (1903–1974), and Mark Rothko (1903-1970)—whose shared summers in Gloucester, Massachusetts, from the 1920s to the mid-1940s had a lasting impact on their work. The exhibit is being presented through a collaboration between the […]

  • Sat 5

    Michalak Fine Art Open Studio

    September 5 @ 11:00 am - 5:00 pm Michalak Fine Art Open Studio

    Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]

  • Sat 5

    Windhover Center for the Performing Arts presents Samãgata: Solo Dances From the Indian Tradition

    September 5 @ 7:00 pm - 9:00 pm
    Windhover Center for the Performing Arts 257R Granite Street, Rockport, MA, United States

    Samāgata {Sanskrit: to come together} performance by Sapna Govindan, Soumya Rajaram, and Priya Bangal In the Indian tradition, music, poetry, dance, painting, sculpture, literature, legend and myth are all inseparably linked in a vast tapestry of art and aesthetics. For a dancer, immersion in her practice involves an awareness of these subtle yet vital connections […]

  • Sat 5

    Folk Week ’26: Henry Acker Trio

    September 5 @ 7:00 pm - 9:00 pm
    Movement Arts Gloucester MA 11 Pleasant Street, Gloucester, MA, United States

    Some of the most impressive guitar playing out there - an evening of Manouche, also known as Gypsy Jazz - virtuosic and highly expressive music that originated in 1930’s France. Henry Acker is a young powerhouse jazz guitarist who performs both in the style of Django Reinhardt as well as in the traditional jazz style. […]

    $25
  • Sat 5

    Sunset Sessions at the Birdseye Rooftop

    September 5 @ 7:00 pm - 10:00 pm Sunset Sessions at the Birdseye Rooftop
    Beauport Hotel 55 Commercial Street, Gloucester, MA, United States

    Enjoy the weekend in style at Sunset Sessions. An evening of vibrant energy, coastal glamour, and unforgettable harbor front views at Beauport Hotel’s Birdseye Rooftop. Join us during our 10th year by the sea, every Friday and Saturday evening for a lively celebration featuring DJ entertainment from The 617 Event Group. Dance as the sun […]

    $30
  • Sat 5

    Birdseye Rooftop Sunset Sessions: Summer’s Grand Finale Fireworks

    September 5 @ 7:00 pm - 10:00 pm
    Beauport Hotel 55 Commercial Street, Gloucester, MA, United States

    Celebrate Labor Day Weekend, and the grand finale of Beauport Hotel Gloucester's 10th summer by the sea, with an unforgettable evening at Birdseye Rooftop! Enjoy panoramic harbor views, live DJ entertainment, handcrafted cocktails, and the best seat in town for Gloucester's spectacular fireworks display. As the sun sets, take in the vibrant rooftop atmosphere before […]

    $30
  • Sat 5

    Beauport Cruiselines Labor Day Weekend Cruise

    September 5 @ 7:00 pm - 10:00 pm
    Beauport Cruiselines 6 Rowe Square, Gloucester, MA, United States

    Celebrate the unofficial end of summer in unforgettable style at our annual Labor Day Weekend Fireworks Cruise on Saturday, September 5th from 7:00PM–10:00PM! Step aboard for an evening of breathtaking views as we cruise through the scenic Gloucester Harbor at sunset. Enjoy a decadent Prime Rib dinner buffet featuring delicious seasonal favorites, sip handcrafted cocktails […]

    $92
  • Sun 6

    Cape Ann Plein Air’s Schooner Festival Paint Out

    September 6 @ 9:00 am - 1:00 pm
    Stacey Boulevard Gloucester, United States

    Join us for the Gloucester Schooner Festival Paint Out on Sunday, September 6, 2026, and capture the beauty of one of Cape Ann's most iconic events. From majestic schooners and colorful maritime flags to blooming dahlias, the sparkling ocean, historic waterfront, and bustling festival atmosphere, inspiration will be everywhere. Artists will paint throughout the morning, […]

  • Previous Events
  • Today
  • Next Events
  • Google Calendar
  • iCalendar
  • Outlook 365
  • Outlook Live
  • Export .ics file
  • Export Outlook .ics file

Keep in touch

Stay up to date with events, festivals and news!
  • Dining
  • Shop
  • Stay
  • Events
  • Things to Do
  • Dining
  • Shop
  • Stay
  • Events
  • Things to Do
  • Weddings
  • Group Tours
  • Plan Your Visit
  • FAQs
  • About Discover Gloucester
  • Partners
  • Weddings
  • Group Tours
  • Plan Your Visit
  • FAQs
  • About Discover Gloucester
  • Partners

info@discovergloucester.com

Loading Comments...