Every morning we round up what’s happening in Gloucester and Rockport — the fairs, markets, pop-ups, waterfront happenings, library programs, school and community events — all in one place, so you don’t have to go hunting for it. Under the flyer, every event links back to the folks putting it on, so you can get the details straight from them. We keep it local — Gloucester and Rockport only — and we keep it to the good community stuff. Here’s what’s on:
What’s coming up around Gloucester and Rockport — tap an event for the details:
Monday, November 16
The GLL Masters — Gloucester Little League Indoor Golf Tournament — Monday, November 16, Flight 1 at 5:30 PM and Flight 2 at 7:30 PM, Harbor 9 Golf, Gloucester. Indoor golf tournament, raffle and social event to benefit Gloucester Little League. Two-man scramble, $200 per team. Championship Round is Tuesday, November 17 at 6:00 PM. Special guest Marc Lewis on November 16, with a special performance by Bruins anthem singer Todd Angilly.
Thursday, November 19
Artful Conversations: “Baptism,” by Anne Rearick — Thursday, November 19, 12:30 – 1:30 PM, Cape Ann Museum, 27 Pleasant Street, Gloucester. Informal, docent-led look in depth at Baptism by photographer Anne Rearick, whose work is featured in the Museum’s special exhibition. Registration required.
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Every morning we round up what’s happening in Gloucester and Rockport — the fairs, markets, pop-ups, waterfront happenings, library programs, school and community events — all in one place, so you don’t have to go hunting for it. Under the flyer, every event links back to the folks putting it on, so you can get the details straight from them. We keep it local — Gloucester and Rockport only — and we keep it to the good community stuff. Here’s what’s on:
What’s coming up around Gloucester and Rockport — tap an event for the details:
Sunday, November 8
1. Renaissance Faire at Hammond Castle Museum — 9:00 AM – 5:00 PM, Hammond Castle Museum, 80 Hesperus Ave, Gloucester. Knights, armored combat demos, medieval arms and armor, storytelling, music and hands-on fun for kids. Costumes encouraged; free parking and shuttle from Stage Fort Park.
2. Walking Tour: Historic Dogtown – A Walk Back in Time — 10:00 AM – 12:00 PM, Babson Boulder Parking, Cherry Street, Gloucester. Last Dogtown walk of the season – cellar holes, stone walls and tales of old Dogtown. Registration required.
3. Holiday Market at North Shore Arts Association — 12:00 – 4:00 PM, North Shore Arts Association, 11 Pirates Lane, Gloucester. Final day of NSAA’s final open weekend of 2026 – artwork, ceramics, jewelry, textiles and more, with hot cider and coffee.
4. The Great Marsh Starts Here! A Living Landscape in Motion — 12:00 – 5:00 PM, Cultural Center at Rocky Neck, 6 Wonson Street, Gloucester. Free exhibition by the Great Marsh Artists Fellows. Open Friday-Sunday, noon-5, through November 22.
Tuesday, November 10
5. Highlights Tour: An Introduction to the Galleries — 11:00 AM – 12:00 PM, Cape Ann Museum, 27 Pleasant Street, Gloucester. Docent-led introduction to the galleries. Free with general admission, drop-in.
6. Women’s Night of Thanks — 6:00 – 8:00 PM, Community Church of East Gloucester, Gloucester. The church’s annual Women’s Ministry Night of Thanks in the fellowship hall. Please RSVP.
7. Beauport Sessions — 6:00 – 9:00 PM, 1606 Restaurant & Oyster Bar, Beauport Hotel, Gloucester. Tuesday-night live music series at 1606 inside the Beauport Hotel.
Wednesday, November 11
8. Fish Tales: Veterans – What It Means, What It Meant — 7:00 PM, Gloucester Stage, 267 East Main Street, Gloucester. On Veterans Day, Gloucester Writers Center presents true stories told live by and about veterans.
10. Captain Elias Davis House Tour — 2:00 – 3:00 PM, Cape Ann Museum, 27 Pleasant Street, Gloucester. Step inside the Davis House and see what a house tells us about the people who lived there. Free with general admission.
12. Rockport PTO Holiday Fair — 9:00 AM – 1:00 PM, Rockport High School, 24 Jerdens Lane, Rockport. 50+ vendors, surprise jars, gingerbread houses, pictures with Santa, raffles and more.
13. AI’s Promise and Peril: A Conversation — 1:00 – 3:00 PM, Kyrouz Auditorium, Gloucester City Hall, Gloucester. Gloucester Lyceum, with Sawyer Free Library – a free community conversation on AI, work, privacy and daily life. Registration required.
14. This Other Eden: Photographs by Anne Rearick – Opening Day — Opens today – Members’ Reception 3:00 – 5:00 PM, Cape Ann Museum, 27 Pleasant Street, Gloucester. More than 60 photographs of life at Stage Fort Park by longtime Gloucester resident Anne Rearick. Runs through March 21.
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Cape Ann SUPahBowl, Gloucester’s biggest paddle board racing event, brought more than 60 contestants to Pavilion Beach at Beauport Hotel early this morning. It was a rainy start but gave way to a beautiful day on Gloucester Harbor.
Congratulations on a such an amazing launch Cape Ann SUP! And to all who pulled this together including Beauport Hotel, High 5EM event management company, Barefoot Wine (the largest wine spritzer company in the country I was told- who knew?), One Ocean One Love retail shop, and a big family of volunteers and staff.
The race had staggered starts for 4 various classes: elite, amateur, open and kids. The elites kicked it off and had the longest distance course. The video shows the start of the first two groups heading off to turn right… at the Greasy Pole! Coast guard and police boats were on hand and a paddle board pit stop at each buoy should any help be necessary. Photos from today’s event below.
They’re off!
video of the first 3 minutes – elite and amateur racers start from dry land
They’re off – open race starts in the water
They’re off – kid’s race starts in the water
map for the 2.5 mile open course
Returning Racers
Racers return to Pavilion Beach after grueling courses. Cape Ann SUP (red t-shirts) staff wait to carry and beach each and every board as contestants dismount and sprint –carrying their paddles — through to the official finish line and timer.
Finished racers await other contestants and times. Many knew each other and competed in all 4 races of summer 2017.
Vinnie, Dominic’s dad (white shirt), worked throughout the event (setting up finish line here with High 5em!) and worked through the celebration. “It’s a family effort and affair,” he said speaking to how the race is put on and who it caters to. There was a tremendously positive vibe!
Participants get a sweet t shirt
Excitement in the air at registration prep
lobster course buoys
Dominic explains the race course to more than 60 participants first ever Cape Ann SUPahBowl 2017
Barefoot wine
Collin Jackson, Mara Hale, Nicole Brosch, Britta Akerley
The view from the Beauport Hotel deck is a sweeping stunner! Before the awards ceremony and reception were held, Barefoot Wine, Cape Ann SUP and One Ocean One Love shop were readying the event space with Beauport Hotel.
AWARDS CEREMONY AND RECEPTION
Gentle and fun crowd of racers. There was serious prize money and cute swag. All participants received the sweet inaugural t-shirt.
Anneliese Brosch and Dominic attend to every detail
Mens elite
Womens elite
Kids win
Johnny
mens Grand winner all 4 events
Nice to see so many families and future racers!
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The Figli di Trappeto Club is hosting their 7th annunal International Womens Day Celebration ~ “Festa Della Donne” at The Gloucester House this evening. FOB and one of Gloucester’s most famous and loved reporters Carl Mckay-Stratton will be live blogging for GMG at tonight’s “SOLD OUT” event!
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This past weekend was yet another insanely jam packed weekend full of events. Not just a few small ones either- there was a TON to cover.
Well the staff really shined as we covered a whole lot of Gloucester goodness
The Kevin Riley benefit game
The Farmer’s Market
The Paula Karahalis concert at Harbor Loop
The Clean Harbor Swim
The Rocky Neck Trot
The JJ Nicastro foundation Kidz Fun Day
The opening at Pop Gallery
The Downtown Gloucester Block Party
Nelson’s Ride
The Inaugural Ocean Pursuit sailboat race video (coming)
and of course Run Gloucester
The task at the beginning of the weekend seemed daunting but once again the dedicated and passion filled GMG staff captured the essence of Gloucester for our local readers as well as the homesick ex-patriots that have unfortunately moved away for one reason or another.
We brought it all home and have much more from this weekend including Magnolia sidewalk bazaar videos and more coverage from the Kevin Riley benefit and Run Gloucester to share with you.
Would you look at that list of events above? They are each huge all by themselves and in most other cities or towns would carry them for an entire month and that was just one weekend here in Gloucester. How lucky are we?
Great job team!
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