2026 Gloucester Schooner Festival Schedule of Events and Ticketing Information

Posted on by Joey Ciaramitaro

 MARITIME GLOUCESTER 

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 GLOUCESTER 

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 at DiscoverGloucester.com

Community/Partner Events:

7:00pm to 9:30pm

Harbor Loop Concert Series

check out more info at DiscoverGloucester.com

boats-22
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 GLOUCESTER 

Museums and Exhibits Open

 Schooner Deck tours 

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. ​

Check various schooner 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.​

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

Heritage Days_-54.jpg
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 GLOUCESTER 

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 TOURS 

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 SAILS 

The public is invited to purchase tickets aboard participating schooners. 

​

Check various schooner websites for ticketing details

6:30pm to 10:30pm*

 FIREWORKS SAILS 

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

Check various schooner websites for ticketing details

*sail times approximate, please check individual vessel tickets

Community/Partner Events:

6:30pm to 10:00pm

 Concert on Stacy Boulevard 

Live Music and light effects

More details at facebook.com/ConcertsOnTheBoulevard

7:00pm to 9:00pm

 Boat Parade of Lights 

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 Harbor 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 GLOUCESTER 

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 Races 

Shuttle Bus to Eastern Point Light From St. Anthony’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 SCHOONERS 

The public is invited to purchase tickets aboard participating schooners. ​

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. 

​

The public is invited to purchase tickets aboard participating schooners. ​

Check various schooner websites for ticketing details

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

Posted on by Joey Ciaramitaro
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Not all Gloucester Waterfront Legends Are Fishermen. Here’s EDG- “Every Day Guy” Also AI research on the make and model year of his Vintage Grady White

Posted on by Joey Ciaramitaro

This boat is a vintage 1973 Grady-White Atlantic Weekender 19′ lapstrake cuddy cabin cruiser.

Key Characteristics:

  • Make/Manufacturer: Grady-White Boats
  • Model: Atlantic Weekender 19′
  • Era/Year: Circa 1973
  • Distinctive Features: The boat features a classic tan-accented fiberglass hull with lapstrake-style strakes, characteristic trapezoidal cabin windows with a light-green privacy curtain, a raised wraparound windshield, and a prominent bow rail.

If you are trying to find historical documents, parts, or communities for this specific model, let me know if you would like me to look up:

  • Original specifications or brochures from Grady-White’s early 1970s lineup.
  • Dedicated owners’ clubs or restoration forums for vintage Grady-White models

Tuesday afternoon

Posted on by Donna Ardizzoni

Terry and I love our Tuesday afternoon at the Welcoming Center at Stage Fort Park.  The visitors enjoy are wonderful and beautiful park.  Tuesday was beautiful and there was a photo shoot going on at the Gazebo.

 

Surfside Subs WICKED WEDNESDAY IS HERE! 🍕🔥

Posted on by Joey Ciaramitaro

Make Wednesday dinner easy with some seriously good specials! 🙌

🍕 Buy any 18” Pizza & get the second 18” HALF PRICE!
Limit 2 per customer

⭐ BONUS SPECIALS ⭐
🦞 $19.99 + tax Lobster Roll served with Chips & Pickles
🍕 Buy any 16” Pizza & get the second 16” HALF PRICE!
Limit 2 per customer

Grab your favorite pizzas, add a lobster roll, and make it a Wicked Wednesday! 😍🍕🦞

Excludes gluten free
Pizza specials cannot be combined
Excludes online orders

Real feel Summer: Third week of June-Sept 29. Real feel Fall October 1-December 15. Real Feel Winter December 16-May 1. Real feel Spring May 2-Third week of June.

Posted on by Joey Ciaramitaro

The way people act seasons are way different. Summer June 1-August 31. Fall Sept 1- December 7. Winter December 8-March 31. Spring April 1-May31. That’s it.

Did I get it right?

Discuss.

Update from Toro BBQ in Essex

Posted on by Pat D

New signage was spotted on Eastern Ave in Essex at the site of the former Vita Bella (formerly Windward Grille). Toro BBQ can be found on Facebook at this link to follow for updates: https://www.facebook.com/torobarbecuesteakhouse/

This Week at The Cut

Posted on by Joey Ciaramitaro

 ~ The Cut Live ~ 

Another GREAT week of shows at The Cut! And this is your LAST week to snag one of the insanely delicious Detroit style pizzas from BRAVO2 as their extended pop-up at The Cut is coming to a close. We will be sad to see them go, but we are also very excited to welcome Publick House at The Cut. They’ll be opening on Tuesday, September 1st 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.

BRAVO2 will be serving a limited menu of PIZZA ONLY Wednesday (8/26) through Sunday (8/30) as we prepare to transition to The Publick House.

Wednesday we have The Meditations. This show is part of the Legends of Reggae Series presented by Happy Valley. Doors at 7pm. Show at 8pm. There are still tickets available!
Plus George Clements & Joe Wilkins will be playing a live acoustic set in the restaurant from 6pm – 9pm. No Cover.

Thursday hop aboard and sail away with Thurston Howell – The Yacht Rock Spectacular! Doors at 7pm. Show at 8pm. Seats are almost gone, but there are still GA Standing (AKA dancing) tickets available.

Friday is Jeff Pitchell & Texas Flood. Doors at 7pm. Show at 8pm. There are still tickets available.
We also have The Crab Elastic live in the restaurant from 7pm – 10pm. No cover!

Saturday is Duke Robillard in the venue. Doors at 7pm. Show at 8pm. There are still some tickets available.
Plus DJ Vito will be throwing it down in the restaurant starting at 9pm. No cover!

Sunday is Deric Dyer – A night of stories and music from his years touring with Tina Turner and Joe Cocker. Doors at 6pm. Show at 7pm. There are still some tickets available.  

BRAVO2 – The FINAL week. Come get yourself one of those killer Detroit style pizzas one last time before they’re gone!
The Hours this Week are:
Wed 5pm – 9pm – SERVING PIZZA ONLY
Thu 5pm – 9pm – SERVING PIZZA ONLY
Fri 5pm – 10pm – SERVING PIZZA ONLY
Sat 5pm – 10pm – SERVING PIZZA ONLY
Sun 12pm – 9pm – SERVING PIZZA ONLY

The Publick House at The Cut opens 9/1 and will be open for lunch and dinner 7 days a week!

THE MEDITATIONS TICKETS

THURSTON HOWELL TICKETS

JEFF PITCHELL TICKETS

DUKE ROBILLARD TICKETS

DERIC DYER TICKETS

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

GET MEMBERSHIP DETAILS HERE

HOURS:
MON CLOSED, TUE CLOSED, WED 5PM, THU 5PM, FRI 5PM, SAT 5PM, SUN 12PM

THE CUT | 177 Main Street | Gloucester, MA

Visit Our Website

Buy Tickets to a Show

This Week at The Cut

2026 Luminaries & Love Event, taking place on August 31 (rain date: September 1). This special community gathering is a peaceful evening of healing, remembrance, and support as we remember loved ones lost to substance use and stand beside the family members and friends they left behind.

Posted on by Joey Ciaramitaro

Each year, more than 1,500 luminary bags line the boulevard, creating a beautiful tribute to those we have lost. Canned goods are used to weigh down the bags and are then donated to The Open Doorto help feed our community. In 2025, our community donated an incredible 2,007 pounds of food in memory of loved ones.

How You Can Help

Attend this peaceful healing ritual.
Join us in remembrance and help show grieving community members that they are not alone. Your presence helps create a powerful message of love, compassion, and hope.

Bring canned goods to the event.
Donations of canned goods can be brought directly to the event on August 31 (or September 1 if the rain date is needed).

Donate before the event.
Amazon wish list or canned goods can be dropped off through Sunday, August 30at the following locations:

  • Cape Ann Lanes
  • Middlesex Recovery
  • West Gloucester Trinitarian Church
  • Cape Ann YMCA
https://www.amazon.com/registries/gl/guest-view/12D3MHJ9NH5CP?ref_=cm_sw_r_cp_ud_ggr-subnav-share_W8HDH96GB2DRJKRKGCQH

Volunteer for setup or breakdown.
Volunteers are always needed. Setup begins after 3:00 p.m. at the Flagpole. Any amount of help is greatly appreciated incuding breakdown beginning around 8pm. It is a labor of love.

Help Preserve the Luminaries

Last year’s event was impacted by rain, and many of the luminary bags are fragile. Over the past year, volunteers have carefully repaired hundreds of bags. Attendees are encouraged to locate their bag from previous years and create a new one if it needs replacement.

Bags, markers and LED Lights are provided. Children are encouraged to draw chalk hearts and blow bubbles (provided).

If weather requires us to move to the rain date, an announcement will be posted by 3:00 p.m. on August 31 on the Gloucester Annual Overdose Vigil Facebook page.

As always, thank you to our community for coming together to make this meaningful night possible. Through remembrance, compassion, and collective support, we continue to honor those we have lost while bringing comfort and healing to those who carry their memory forward.

Together, let’s Light the Boulevard with Love.

Surfside Subs LOBSTER ROLL TUESDAY! 🍕🦞

Posted on by Joey Ciaramitaro

Tuesday just got even better! Stop in and take advantage of TWO great specials today:

🦞 $13.99 + tax Lobster Roll
Served with chips & pickles

🍕 BONUS SPECIAL:
Buy any 16” pizza and get a 2nd 16” pizza HALF PRICE!
*Limit of 2 per customer

Grab lunch, dinner, or both and enjoy a delicious Tuesday deal! 😋

*Excludes gluten free
*Excludes online orders

Time for One More Schooner Challenge Tonight

Posted on by Pat D

As I have noted previously we try to get out for the weekly Schooner Challenge through Maritime Heritage Charters held most Tuesdays throughout the summer. Last week was no exception. Each experience is unique as the passengers are part of a “lesson plan” for the program apprentices. At least one more Challenge is scheduled for tonight (weather permitting of course) so it’s a good time to plan to come along. AND there are Tuesday discounts offered, so it’s a win-win. See you out there!