2026 Gloucester Schooner Festival Schedule of Events and Ticketing Information

MARITIME GLOUCESTERย 

Schooner Challenge
THURSDAY Sept 3 2026

COMMUNITY DAY

A day filled with local flavor.  Local captains and crew will be making the rounds throughout the community, culminating in an evening race sure to wake up the harbor!

On Land: 10:00am to 4:00pm MARITIME GLOUCESTERย 

Museums and Exhibits Open

Come Sailing: 5:30pm to 7:30pm

 SCHOONER CHALLENGE

Join our local Schooner Captains as they participate in a friendly competition putting their seamanship to the test over an “obstacle” course. Passengers will be given their own set of tasks to win the coveted Rum Bottle Award. Visiting schooners already arrived will join the event. The public is invited to purchase tickets aboard participating schooners. Ticketed passengers and crew will be invited to a post challenge awards party. 

Check various schooner websites for ticketing details

4:00pm to 7:00pm Culture Splash check out more info atย DiscoverGloucester.com

Community/Partner Events: 7:00pm to 9:30pm Harbor Loop Concert Series

check out more info at DiscoverGloucester.com

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FRIDAY
Sept 4, 2026 GREET THE FLEET DAY

As visiting sails cross the breakwater, Gloucester Harbor comes alive again, harkening back to the golden days of our Fishing Fleet under sail. This day signals the annual pilgrimage of historic wooden vessels returning to Gloucester Harbor. 

On Land: 10:00am to 3:00pm MARITIME GLOUCESTERย 

Museums and Exhibits Open- Schooner Deck toursย – Schooner Floats at I4C2 10am-1pm

Come Sailing:10:00am to 5:00pm

 PUBLIC SAILS 

The public is invited to purchase tickets aboard participating schooners. โ€‹

Check variousย schoonerย websites for ticketing details Various Departure Times

 GREET THE FLEET SAILS 

Historic Gloucester Harbor comes alive with canvas as traditional wooden vessels. With so many schooners in the harbor, here is your opportunity to be part of the action! A thrilling chance to greet visiting schooners as they come over the breakwater.โ€‹

Check various schooner websites for ticketing details

Community/Partner Events: 7:00pm to 10:00pm Chamber of Commerce Block Party

check out more info Here

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SATURDAY Sept 5, 2026 MARITIME HERITAGE DAY

The festival’s biggest spectator day, with 3 locations to engage with history and vessels, dozens of opportunities to get on board and view these majestic ships or sail on Gloucester Harbor. The pinnacle of the festivities revolve around Maritime Gloucester’s pier with demonstrations and family fun.

Check out the day’s schedule HERE

On Land: 10:00am to 4:00pm MARITIME HERITAGE DAY AT MARITIME GLOUCESTERย 

Museums and Exhibits Open, Schooner Deck Tours

Free to the public: schooner deck tours, music, food trucks, USS Constitution 1892 Marines, crafts for all ages, skills demonstrations, community vendors, & family activities. 

$25 hourly schooner sails on Schooner Ardelle!

Get your MHD schedule and details HERE

12:00pm to 4:00pm SCHOONER DECK TOURSย 

Schooner Floats – I4C2, 65 Rogers St 

Ocean Alliance – 32 Horton St, Rocky Neck

Thanks to generous support from our sponsors, we are again able to provide a visitor-based dockside experience that puts the public on schooners for deck tours. This is a free option for the public, but donations are always appreciated.

Come Sailing: 8:30am to 6:00pm PUBLIC SAILSย 

The public is invited to purchase tickets aboard participating schooners. 

โ€‹Check variousย schoonerย websites for ticketing details

6:30pm to 10:30pm* FIREWORKS SAILSย 

Witnessing the fireworks over historic Gloucester Harbor is a magnificent sight. Seeing it above you from the deck of a schooner is a breathtakingโ€‹ experience you do not want to miss. These sell out quickly, so don’t delay. 

Check variousย schoonerย websites for ticketing details *sail times approximate, please check individual vessel tickets

Community/Partner Events: 6:30pm to 10:00pm Concert on Stacy Boulevardย 

Live Music and light effects More details atย facebook.com/ConcertsOnTheBoulevard

7:00pm to 9:00pm Boat Parade of Lightsย 

This annual event showcases a parade of local private boats and begins at dusk in the Annisquam River. 

For more information: facebook.com/boatparadeoflights

9:15pm Fireworks Display over the Harborย time is approximate

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SUNDAY Sept6 2026

RACE DAY! The capping day of events culminates in the gorgeous spectacle of the Parade of Schooners and the Offshore race for the Mayors’ Cup.

On Land: 10:00am to 4:00pm MARITIME GLOUCESTERย 

Museums and Exhibits Open 10:00am to 11:30am

 Parade of Schooners 

Schooners proceed from the Inner Harbor, past the Fisherman’s Memorial on Stacy Boulevard and Stage Fort Park, to the race starting area off Eastern Point. Various non-profit and business organizations offer Parade of Schooners or Race viewing opportunities.

10:30am to 2:30pm Shuttle to Watch Racesย 

Shuttle Bus to Eastern Point Light From St. Anthonyโ€™s Church, Farrington Ave to watch the start of the Mayor’s Race. Free of Charge courtesy of the Cape Ann Transportation Authority. Thank you to the Holy Family Parish for allowing us to use their parking lot.

1:00 pm Schooner Races

Start of Mayor’s Races for the Esperanto Cup & the Columbia Trophy Off Eastern Point – the race course is decided the morning of the race by the Schooner Festival Committee at a meeting with the captains of the participating vessels.

Come Sailing: 9:00am to 12:00pm PARADE OF SCHOONERSย 

The public is invited to purchase tickets aboard participating schooners. โ€‹

Check various schooner websites for ticketing details

various departure times, check schooner schedule

 MAYOR’S CUP RACE 

The Mayor’s Cup, Esperanto Trophy, and many other awards are up for grabs in this thrilling off-shore race. The race course positions are decided the morning of the race by the Schooner Festival Committee at a meeting with the captains of the participating vessels. 

โ€‹The public is invited to purchase tickets aboard participating schooners.ย โ€‹

Check various schooner websites for ticketing details

GMG Navigation- Get Started Here. Subscribe, Find, See, Do. Immerse Yourself In The Good Morning Gloucester World.

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Minglewood Harborside Nacho average craving. Piled high and impossible to shareโ€ฆeven if you say you will

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Surfside subs Thursday 9/3 is looking extra delicious! ๐Ÿฆž๐Ÿ•๐Ÿ”ฅ

๐Ÿฆž Lobster Roll Special โ€” $17.99 + tax
Served with chips & pickles!

๐Ÿ• 16โ€ Pizza Special
Buy any 16โ€ pizza and get the 2nd 16โ€ pizza HALF PRICE!
Limit 2 per customer

๐Ÿ• 18โ€ Pizza Special
Buy any 18โ€ pizza and get the 2nd 18โ€ pizza HALF PRICE!
Limit 2 per customer

Excludes gluten free
Pizza specials cannot be combined
Excludes online orders

Night Lights at St. Peter’s Dock

As we were leaving Minglewood after dinner recently, I noticed how the still waters in the harbor reflected the lights. I hope you find it as beautiful and peaceful as I did.

Brandon Pratt saving people a lot on Homeowners insurance.

ย byย prattbrandon

On Friday I got to catch up with Joey Ciaramitaro from Good Morning Gloucester to talk about the latest with mortgages, homeowners insurance and Florida homebuying.

Homeowners insurance keeps going up, especially in coastal communities. I work with many local insurance agents and I would be happy to help anyone shop their homeowners insurance to try to get it lowered (I am licensed in Mass as a Insurance Producer). I just helped Joey and Katelyn lower their insurance by $1500/year this month.

If you are thinking about buying in Florida, now is the time to start looking. I am licensed in Florida as well and just helped Joey and Katelyn buy a condo in Naples FL this month. We have a great real estate agent we work with down there too to help!

If you need any assistance in any of these areas, or any other real estate questions,

Contact Brandon Pratt www.northshorehomeloans.com or 617-688-6891

44 Main Extensive hours this week including Friday nightโ€™s Downtown Gloucester Block Party!

Canโ€™t wait to see you at 44 Main Street this weekโ€™s hours:
Thurs Sept 3 from noon-5;
Friday 10-1 and Block Party;
Saturday 11-4;
Sunday noon-3; and Labor Day 11-3.

Shop online https://gloucesterapparel.square.site/

Magnolia Pier

After a rainy Tuesday, the sky started to clear up with a touch of fog.ย  As can be seen, the ramp and float are still out of the water for needed repairs.

Final Events at Windhover this Season

Final Events at Windhover this Season
Sure enough, the days are getting shorter, the breeze is cooler, and we look to see if there are traces of color in the trees, hoping that fall will wait outside just a while longer before busying our lives. Here at Windhover, thankfully itโ€™s still summer for a while longer โ€” with picnic tables for informal gatherings, and, of course, music and dance this week, and a community gathering to support The Open Door toward the end of August. We say โ€œa while longerโ€ as in while away an hour or two, celebrating together, as only art can, the precious passing of time, day to day, season to season. And speaking of celebrating โ€” what a lovely, heartwarming Gala Summer Celebration it was last week!  Deep thanks to all who joined us as we gathered as a community to remember just why we do what we do – bringing talented performing artists to this special place and giving audiences the chance to appreciate them.  And we still have more in store for this month of September:
Samฤgata: Solo Dances from the Indian Tradition
Friday, September 4 at 6:30pm under the tent is a music performance by โ€œWood and Bone,โ€ a North Shore favorite with Americana roots and blues tunes. And opening the show will be the rock classic band โ€œKicked off the Busโ€ based in Gloucester. Tickets can be found hereSaturday, September 5 at 7:00pm under the tent are several classical Indian dancers performing solos which display three different dance forms from India. The show is titled: โ€œSamagataโ€ which means โ€œto come togetherโ€ in Sanskrit. More information and tickets can be found here.Lastly, Windhover reaches out to the greater community of Cape Ann on Sunday, September 27 from 2:00-4:00pm when Cape Ann Cake Fest takes center stage with a festivity inspired by The Great British Bake Off. Participants bring a cake to share with others, and everyone goes home with a cake box of samplings that you choose to taste and bring home. This event is ticketed and supports both the Open Door and Windhover. The Open Door is a community-focused non-profit organization dedicated to easing the impact of hunger through its programs and outreach. More information and tickets can be found here.Please come and participate during these last lingering summer days where you can share music, dance and foodโ€ฆyes, cakesโ€ฆ all with a sense of community and sharing.
With warm wishes,
Lisa Hahn, Windhover Executive Director
Duncan Hollomon, Windhover Board Member

Your Donation is Welcome
We rely on community support and you to continue producing dance, drama, music and poetry at Windhover. Please consider donating to Windhover, a non-profit 501ยฉ3 organization by going to: www.windhover.org/donateAll donations are tax deductible

Surfside Subs WICKED WEDNESDAY IS HERE! ๐Ÿฆž๐Ÿ•

Make your Wednesday a little more delicious with some seriously good specials! ๐Ÿ™Œ

๐Ÿ• Buy any 18โ€ Pizza and get the 2nd 18โ€ Pizza HALF PRICE!
Limit of two per customer

โญ BONUS SPECIALS โญ
๐Ÿฆž $17.99 + tax Lobster Roll served with Chips & Pickles
๐Ÿ• Buy any 16โ€ Pizza and get the 2nd 16โ€ Pizza HALF PRICE!
Limit of two per customer

Grab your favorites and let us take care of dinner tonight! ๐Ÿ˜‹

Excludes gluten free
Pizza specials cannot be combined
Excludes online orders

Don’t Miss Schooner Fest 2026!

My favorite event of the year is on our doorstep: Schooner Festival to be held Sept 3-6 this year. I am looking forward to seeing all the guest schooners at the local docks and in the harbor. I hope to spend significant time on board our local schooners. I hope you do too! Here’s some memories from previous years to whet your appetite. Stop by 44 Main St to check out our various schooner related items including hats, shirts, sun catchers, notecards and nightlights. Open noon-5 Thursday, 10-1 Friday (Block Party!); 11-5 Saturday and noon-3 Sunday.

This Week at The Cut

 ~ THE CUT LIVE

Another GREAT week of shows at The Cut! And this week Publick House at The Cut takes over the restaurant! Theyโ€™ll be opening on Wednesday, September 2nd at 11am and will be operating seven days a week for lunch and dinner! You can find out more about The Publick House at The Cut HERE.

Thursday we have Abraxas โ€“ Santana Tribute. Doors at 7pm. Show at 8pm. There are still some tickets available.

Friday 
is Mighty Mystic with Double TigerDoors at 7pm. Show at 8pm. This show is part of the Legends of Reggae Series presented by Happy Valley. There are still tickets available.
We also have Clay Pigeons live in the restaurant from 7pm โ€“ 10pm. No cover!

Saturday is Barry Goudreauโ€™s Engine Room in the venue. Doors at 7pm. Show at 8pm. There are still some tickets available. 
Plus DJ Skully will be throwing it down in the restaurant starting at 9pm. No cover!

Publick House at The Cut takes over this week. 
The Hours this Week are: 
Wed 11am โ€“ 10pm
Thu 11am โ€“ 1am 
Fri 11am โ€“ 1am 
Sat 11am โ€“ 1am 
Sun 11am โ€“ 10pm

The Publick House at The Cut opens 9/2 and will be open for lunch and dinner 7 days a week!

ABRAXAS TICKETS

MIGHTY MYSTIC TICKETS

BARRY GOUDREAU TICKETS

The Cut Memberships are always available. Sign up for exclusive presales, perks and privileges!

GET MEMBERSHIP DETAILS HERE


THE CUT | 177 Main Street | Gloucester, MA

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The memorial and celebration of life for David Cox will be held at the Annisquam village church on September 12th with a  service at 10:00 AM and a reception to follow.

To all who knew him and loved him please feel free to come, share stories and celebrate his life โค๏ธ

Block Party FRIDAY NIGHT! Pat Dalpiaz and I Will Have All New Killer Gear Including New Schooner and Lobster Cap styles! Starts at 6PM

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Come by with your peeps so we can take your picture with teh www.goodmorninggloucester.com Instagram Photo Frame

Contact me to order your I Love Gloucester Schooners Hoodies or Pigment Dyed T Shirts