Gloucester Schooner Festival

Gloucester Schooner Festival 2025

The Gloucester Schooner Festival celebrates maritime, sailing and fishing heritage of Cape Ann Massachusetts

The Gloucester Schooner Festival is a  wonderful celebration of Gloucester's fishing and maritime history during labor day weekend. This year's festival, hosted by Maritime Gloucester, is Gloucester’s major marine event, with participating vessels coming from ports along the Eastern seaboard and beyond. There will be both large and small vessels—ranging from 19 feet to over 100 feet in length. You will see new boats and old boats, from newly built (Ardelle - launched 2011) to over 100 years old!

When: 
Labor Day Weekend, August 27-31, 2025
Location: 
Downtown Gloucester
Gloucester Harbor
Gloucester Harbor Walk
Ocean Alliance
Gloucester
Concert
Fireworks
Parade
Outdoor Activity
Festival
History
Sailing
Gloucester Schooner Festival
Schooner

Heritage Day in Gloucester

Maritime Gloucester & Ocean Alliance hosts a day of free exciting demonstrations and interactive fun for all ages in Gloucester Massachusetts.

Maritime Gloucester is hosting their annual Heritage Day in honor of the Gloucester Schooner Festival 2025. Step aboard a schooner, learn about traditional shipbuilding and fitting out, watch America’s oldest marine railway in action, or explore the unique biology that makes our oceans so amazing. You can find it all at Maritime Heritage Day! Maritime Gloucester will be hosting a variety of local community organizations with an exciting array of demonstrations and interactive options for all ages.

When: 
Saturday, August 30, 2025 10am-4pm
Location: 
Maritime Gloucester
Gloucester Harbor Walk
Ocean Alliance
Gloucester
Workshop
Food
Demonstration
History
Games
Art
Gloucester Schooner Festival
Activity
Crafts
Heritage

Schooner Festival Fireworks

The Gloucester Schooner Festival will light up Gloucester Harbor with Fireworks!

Following the Gloucester Schooner Festival's Parade of lights in Gloucester Harbor, A fireworks display will light up the sky over Gloucester Harbor to celebrate a great day of maritime history and tradition.  Good vantage points for viewing fireworks include Gloucester's Boulevard, Stage Fort Park, Pavilion Beach and the

When: 
Saturday, August 30, 2025 9:15pm
Location: 
Gloucester Harbor
Gloucester
Fireworks
Gloucester Schooner Festival

Mayor's Cup Schooner Race

The Mayor's Cup Race at the Gloucester Schooner Festival is just part of the fun

Note: Due to the weather, these events have been postponed to Labor Day Monday. The Mayor's Race is a major part of the Gloucester Schooner Festival 2025, where participating schooners in the weekend activities compete for for the Esperanto Cup, Ned Cameron Trophy and Betty Ramsey Trophy off Eastern Point and East Gloucester.

When: 
Rain Date: Monday September 4, 2017 1pm
Location: 
Gloucester Harbor
Gloucester
Concert
Fireworks
Parade
Outdoor Activity
Festival
History
Sailing
Gloucester Schooner Festival
Schooner

Coast Guard Open House and Tours

Gloucester's US Coast Gaurd Station host an open house at their station in downtown Gloucester!

United States Coast Guard Station Gloucester is having an open house on Saturday, May 14, 2016. Stop by and learn all about the Coast Guard and its important role in Gloucester!  The United States Coast Guard Station Gloucester annual Safe Boating Day Open House will feature local marine vendors, safe boating displays, flare demonstrations, and tours of Coast Guard vessels, and more. Free to the public. Recreational boaters, commercial boaters, Loads of fun for the kids!

When: 
Saturday, May 14, 2016 at 10AM
Location: 
United States Coast Guard Station Gloucester
Gloucester
Tour
Open House
Gloucester Schooner Festival
Coast Guard

Lobster Bake at Maritime Gloucester

Enjoy lLobster on the wharf at Maritime Gloucester duirng the Schooner Festival!

Come to Maritime Gloucester for a community celebration of food, music and Gloucester's Maritime heritage! Enjoy freshly steamed lobster, corn on the cob, and a Virgilio's roll— all for $15 per person!  Where else can you get a boiled lobster for that price?  Relax on the wharf with your dinner or on the slopes of the Fitz Henry Lane lawn while listening to Old Cold Tater & Friends.

When: 
Saturday, August 30, 2014 4:30-7:30pm
Location: 
Maritime Gloucester
Gloucester
Food
Festival
Charity
Gloucester Schooner Festival
Heritage
Lobster
Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich Massachusetts

Babson Farm Quarry Self-guided Walking Tour at Halibut Point
Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

Marblehead Christmas Walk
The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts
The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets,...
Where: Downtown Marblehead
9:00 am to 9:00 pm
♦ Read More →

Salem Witch Hunt Walking Tour
Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

Deck The Halls: Hammond Castle
A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
Where: Hammond Castle Museum
10:00 am to 8:00 pm
♦ Read More →

Christmas at Castle Hill | A Nod to Nature
Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
Where: Castle Hill on the Crane Estate
10:00 am to 8:00 pm
♦ Read More →

Tree Jubilee at Marini Farm
The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
Where: Marini Farm
10:00 am
♦ Read More →

SeaFestival of Trees in Salisbury | Saturdays
Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
Where: Blue Ocean Music Hall
11:00 am to 8:00 pm
♦ Read More →

SeaFestival of Trees in Salisbury
Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
Where: Blue Ocean Music Hall
11:00 am to 8:00 pm
♦ Read More →

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
Where: Salem Trolley
2:00 pm to 9:30 pm
♦ Read More →

Tree Lighting in Marblehead
Marblehead's tree lighting is always a festive occasion to kick off the holidays
The Tree Lighting will take place at the new National Grand Bank Parking Lot on Pleasant Street in Downtown Marblehead this year!  Enjoy the festive atmosphere and live music as the town lights the yearly Christmas tree! Festivities begin at 5:30pm with the tree lighting at 7pm.
Where: Downtown Marblehead
5:30 pm to 7:00 pm
♦ Read More →

SeaFestival of Trees | Blades Night

Celebrate with holiday with the Bruins Mascot at the SeaFestival of Trees in Salisbury Massachusetts
Come tho the SeaFestival of Tree for a special Bruins themed night! Wear your Bruins apparel, meet the Bruins mascot and skate on the Seaaside Ice indoor rink! Enjoy a scavenger hunt through a maze of sparkling trees, visit Santa, and enjoy the candy cane forest. Skate rentals available. 
Where: Blue Ocean Music Hall
6:00 pm to 8:00 pm
♦ Read More →

Hamilton-Wenham Carol Sing & Tree Lighting
Hamilton-Wenham Community hosts a community carol sing and tree lighting in Massachusetts
The Community House Of Hamilton & Wenham invites children to join us for a jolly evening of carol singing and holiday cheer, led by Kimberly Robertson, Music Director for Stage 284! Santa will be arriving in style at about 7:15pm. Free to attend!
Where: Community House Of Hamilton & Wenham
6:30 pm
♦ Read More →

Saturday, December 6

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

Babson Farm Quarry Self-guided Walking Tour at Halibut Point
Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

Marblehead Christmas Walk
The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts
The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets,...
Where: Downtown Marblehead
9:00 am to 9:00 pm
♦ Read More →

Santa Arrives in Marblehead
Come to Marblehead to welcome Santa as he arrives for the Christmas Walk!
Come to the State Street Landing in Downtown Marblehead to welcome Santa as he arrives by lobster boat!  There's plenty of photo ops and Santa's arrival is followed by the Marblehead Christmas Walk Parade. 
Where: Downtown Marblehead
9:00 am
♦ Read More →

Salem Witch Hunt Walking Tour
Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

Christmas at Castle Hill | A Nod to Nature
Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
Where: Castle Hill on the Crane Estate
10:00 am to 8:00 pm
♦ Read More →

2025 Marblehead Gingerbread Festival
The Marblehead Gingerbread Festival is part of the Marblehead Chamber of Commerce's Christmas Walk, and the proceeds will go to benefit the Marblehead Family Fund and the Marblehead Historical Society.
Come see over 100 locally and professionally made gingerbread creations on display at the historic Jeremiah Lee Mansion in Marblehead, MA during this year's Marblehead Christmas Walk. Community members, businesses, and families are building and donating dozens of gingerbread houses, boats and local...
Where: Jeremiah Lee Mansion
10:00 am to 4:00 pm
♦ Read More →

Tree Jubilee at Marini Farm
The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
Where: Marini Farm
10:00 am
♦ Read More →

Reindeer Run 5k
The Reindeer Run 5k Road Race is hosted by the YMCA of Beverly Massachusetts
Get your best reindeer on and join us as we run, walk or prance through Beverly's coastal roads and historic downtown! You may see Santa, his elves and others in festive costume… By participating, you’re not just running a race—you’re supporting the Y’s mission to strengthen our community.
Where: First Baptist Church Beverly
10:00 am to 12:00 pm
♦ Read More →

Deck The Halls: Hammond Castle
A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
Where: Hammond Castle Museum
10:00 am to 8:00 pm
♦ Read More →
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