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

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 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

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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

Visit Our Website

Buy Tickets to a Show

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

Last Gloucester Main Street Block Party of 2026

ย ~ย Greater Cape Ann Chamber of Commerceย ~ย 

Main Street is closing down and coming alive forย Gloucester Block Party #3!ย ย Bring your crew, your dancing shoes, and your appetite for a jam-packed night of live music, incredible street performers, and local flavor.

ย WHEN:ย Friday, September 4 | 6:00 PM โ€“ 10:00 PM (Streets close at 5 PM)
ย WHERE:ย Main Street, Downtown Gloucester, MA
ย ADMISSION:ย Completely FREE!

ย 3 STAGES OF LIVE MUSIC (Starting at 6 PM):

  • The West End:ย Toni & the Treblemakers (6 PM) | Allen Estes (8 PM)
  • Cape Ann Savings Park:ย Dogtown (6 PM) | Jim โ€˜N Tonic (8 PM)
  • The East End:ย In the Pocket (6 PM) | Tony Kaczynski (8 PM)

ย FAMILY FUN & SPECIAL GUESTS:

  • Live performances byย The Real McCoyย (6:15 & 7:30 PM)
  • Meet theย Cape Ann Vernal Pond Team Reptilesย 
  • Face Painting by Miss Wendyย 
  • Sword Play with Captain Jackย 

Dozens of your favorite downtown shops, local restaurants, food vendors, and artisans will be open late with special block party deals!ย 

Donโ€™t miss the ultimate celebration on Cape Ann. Tap the link below to view the full lineup and RSVP!

ย Get the Full Event Schedule Here:๐Ÿ‘‰ย bit.ly/BlockParty-Sept4

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Last day of August 31, 2026

What a beautiful beach and boating 2026 summer.ย  ย On Monday afternoon as usual, went to the beach after work.ย  When I was about to go home, around 6:00, looked around and it was just the seagulls and me.

Three Contemporary Landscape Artists in New COSMOS Gallery Exhibition

LANDINGS 3 VISIONS

Tom Glover, Vanessa Michalak, and Jan Roy

Exhibition Dates: September 4 โ€“ October 11, 2026
Opening Reception: Friday, September 4, 5:00โ€“7:00 PM
Artist Talk: Friday, September 11, 5:00 PM

COSMOS Gallery
20 Pleasant Street
Gloucester, MA 01930
Exhibition website: Landings 3 Visions

THREE CONTEMPORARY ARTISTS TRANSFORM THE ENDURING TRADITION OF PAINTING PLACE

For centuries, artists have looked to the landscape not simply to record the visible world, but to interpret it. From the idealized vistas of the Renaissance through Impressionism and abstraction, successive generations have reconsidered what a painting of a place can be. In contemporary painting, the landscape may remain recognizableโ€”or become only the point of departure.

LANDINGS 3 VISIONS

The next exhibition at COSMOS Gallery in Gloucester, Landings 3 Visions, opens September 4 and features three accomplished New England artists: Tom Glover, Vanessa Michalak, and Jan Roy. Each is an accomplished contemporary landscape artist, and together their paintings explore the territory between observation and interpretation.

Land, sea, forests, rocks, harbors, boats, and the built environment provide the elements; their three visions explore what happens between seeing a place and making a painting of it.

Tom Glover explores the New Hampshire and Maine seacoast through its harbors, estuaries, docks, rocks, boats, water, and changing coastal light. Gloverโ€™s artistic interpretation of the natural scenery exists in the space between realism and abstraction. This practice reflects the longtime influence of painter John Laurent (1921โ€“2005), an American painter renowned for landscapes along the Maine coast. Glover may begin with direct experience, photographs, and sketches, but then uses abstraction to distill a scene, finding its essential forms and colors. Artist website:  Tom Glover

Vanessa Michalak, a Maine native and Gloucester-based artist, approaches the visible world with an exuberant vocabulary of color and expressive gestures. Forests, rocks, water, gardens, boats, and harbors remain recognizable in her paintings, yet observed forms become scaffolding for something more painterly: flattened shapes, unexpected color, energetic strokes, and rhythmic movement across the canvas. As Michalak explains, her paintings are often driven by her love of โ€œexpressive mark making versus subject matter alone,โ€ with nature providing a continual source of inspiration. Artist website:  Vanessa Michalak

Jan Roy takes the transformation of place further. Beginning as a silk-screen artist before focusing primarily on oil painting, Roy brings a strong graphic structure to landscapes, harbors, architecture, and other observed environments. Recognizable imagery may remain, but it is compressed, fragmented, and reorganized into interlocking planes of color and shape, bringing the landscape to the threshold of abstraction. Artist website: Jan Roy

Seen together, the three artists reveal how elastic the centuries-old tradition of landscape painting has become. Glover distills the physical experience of a place; Michalak releases its energy through color and mark; Roy reorganizes it toward abstraction. None abandons the visible world. Each makes something distinctly personal from it.

The title LANDINGS 3 VISIONS reflects that common ground. A landing can be a shoreline, an arrival, or a point of encounter. In these paintings, it also suggests the place where observation meets imaginationโ€”three artists arriving at three very different visual conclusions.

LANDINGS 3 VISIONS continues COSMOS Gallery’s focus on contemporary art by accomplished regional artists and on exhibitions that place their work within broader currents in art and culture.

The exhibition runs September 4 through October 11, 2026. The public is invited to meet the artists at the opening reception on Friday, September 4, from 5:00 to 7:00 PM. An artist talk will be held on Friday, September 11, at 5:00 PM. Admission is free.

Rose Baker Goings On

The joys of September at Rose Baker. Cooler weather and the start of leaves turning. Daily activities can be found by going to www.gloucester-ma.gov, clicking on Departments and scrolling down to the Council on Aging. You can see our newsletter or call 978-325-5812 to get on our mailing list. For events indicating registration, please stop by or call Natalia at the above phone number. Follow us on Facebook โ€“ Rose Baker Senior Center Gloucester

Special things going on:

September 3 โ€“ 10:30 โ€“ Start of Fishtown Players Readers Theaterโ€™s 6 week program.

September 9th โ€“ 10:30 โ€“ Nutrition Education

September 14th & 21st โ€“ 1:00 -Old Salties

September 16th โ€“ 10:30 โ€“ Coffee with Elise

September 24th โ€“ 1:00 โ€“ Keys, Bags, Names, Words โ€“ Hope in Aging & Dementia Documentary (please register)

Movies on Thursdays at 12:30

September 3rd โ€“ Youโ€™ve Got Mail with Tom Hanks and Meg Ryan

September 10th โ€“ Goodbye Girl with Richard Dreyfus and Marcia Mason

September 17th โ€“ Smokey and the Bandits with Burt Reynolds, Sally Field and Jackie Gleason

September 24th โ€“ Splendor in the Grass with Warren Beatty and Natalie Wood

Seniors on the Go Bus โ€“ Please register

September 14th โ€“ Job Lots and Savers/Gourmet Garden

September 21st โ€“ Trader Joeโ€™s/Putnam Pantry

September 28th โ€“ Target and Liberty Tree Mall/Wendyโ€™s

Group Luncheon and Entertainment โ€“ Please register

September 17th โ€“ Danversport – Solid Goldโ€™s Remember the 50โ€™s and 60โ€™s.

December 2nd and 3rd โ€“ Danversport โ€“ The Music and Passion of Barry Manilow

Alice Gardner submits- “Avery, Gottlieb & Rothko: By the Sea Exhibition at Cape Ann Museum”

Donโ€™t miss the special exhibition at Cape Ann Museum which closes on September 27th !

It is a celebration of the works of Milton Avery ( 1885-1965) , Adolph Gottlieb ( 1903-1974) and Mark Rothko ( 1903-1970.) The three artists were friends  and came to Gloucester in the summer  to paint in the 1920โ€™s to the mid 1940โ€™s . The paintings are colorful and exciting and give you a sense of life in Gloucester at that time . You will also get a chance to see the amazing renovations in the Museum – exquisite! Enjoy !

Surfside Subs TUESDAY SPECIALS ARE HERE! ๐Ÿ•๐Ÿฆž

Treat yourself to a Lobster Roll for just $13.99 + tax, served with chips & pickles!

PLUS our bonus pizza special:
๐Ÿ• Buy any 16โ€ pizza and get the 2nd 16โ€ HALF PRICE!
*Limit of 2 per customer

*Excludes gluten free
*Excludes online orders

Bustling Harbor

I absolutely love how, at almost any hour on any given day, you can look out into Gloucester Harbor and see so many different types of vessels. I wanted to wait for a larger fishing boat to come around the corner of Eastern Point Light House before taking this photo, but didn’t have the time. It is definitely not uncommon to catch a photo of a dragger, a lobster boat, pleasure boats (big and small), sailboats, dories, schooners, a yacht….and even, in this photo, an ultra-light hydrofoil! Love where we live!