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12 events found.

Events

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Today
  • September 2026

  • Fri 4

    Cruise Schedule Aboard WEJACK to View the Schooners, Schooner Races, Boat Parade of Lights, Gloucester Fireworks, and Parade of Sail

    September 3 - September 7
    Cape Ann Cruises 63 ROGERS STREET, Gloucester, MA, United States

    How to See the Schooners with Cape Ann Cruises Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water. The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun! See […]

    $100
  • Fri 4

    Captain Elias Davis House Tour

    September 4 @ 2:00 pm - 2:30 pm Captain Elias Davis House Tour
    Cape Ann Museum Downtown Campus 27 Pleasant Street, Gloucester, MA, United States

    What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives of one Gloucester family and the changing history of Cape Ann. This docent-led experience invites visitors to look closely at the details that transform a […]

    Free with General Admission
  • Fri 4

    Gloucester Block Party #3

    September 4 @ 6:00 pm - 10:00 pm
    Locations Vary

    Main Street Gloucester 1-160 Main Street Gloucester MA 01930 5 PM Streets closed off to traffic & parking 6 PM Music Stages Open (x3) *Also look for these Special Guests on Main Street: Balloon Twisting by TBD Cape Ann Vernal Pond Team Reptiles (Captain Jack-TBD) Face Painting by Miss Wendy 6:15 PM Busker-TBD 7:30 PM […]

  • Fri 4

    Folk Week ’26: Wood and Bone with Kicked Off the Bus

    September 4 @ 6:30 pm - 9:00 pm
    Windhover Center for the Performing Arts 257R Granite Street, Rockport, MA, United States

    We are back under the big tent at Windhover for Americana night - in keeping with our goal of elevating local talent, this night features Wood and Bone, a North Shore favorite known for complex and bluesy toe-tapping Americana, with opening act Kicked Off the Bus, Gloucester’s own wildly talented group of students.

    $25
  • 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 U.S. based artist has 5 highly acclaimed albums 4 of which charted top 10 on Billboard and iTunes. He is labeled as a touring machine […]

  • 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! This two-hour session includes a 30-minute beginner sketch lesson. All you need to bring is a sketchbook, pencils, a ruler, and an eraser. Please note: […]

    $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 this engaging literary walking tour during Gloucester’s 400+ celebration and is excited to continue hosting it in partnership with the Gloucester Writers Center. Gloucester has […]

  • 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
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