Gloucester

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

Boat Tour to Misery Island

Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound Massachusetts

Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound. Along the way, hear stories about the rich history of the harbor and how the Misery Islands acquired their unique name. When you arrive, you’ll have 2 hours to explore the trails, open meadows, rocky shoreline, and hidden coves on the island. The Misery Islands are managed by The Trustees. Time allotted is about 3 hours round-trip (30-minute trip to and from the islands, and 2 hours on Great Misery Island). More information about the islands as well as a trail map can be found HERE

When: 
Saturdays through September 13, 2025 11am or 12:30pm

Downtown Gloucester Block Party

Food, music, live entertainment, dance, craft and fun come together for a great

Main Street, Downtown Gloucester Massachusetts comes alive when the Street is closed off to allow live music, street performers, kid activities, non-profits, food vendors and more! Many of shops and businesses on Main Street will be open for business and will welcome partygoers. Other Gloucester businesses and non-profits will be represented on the Street as well. come for a night full of Live music, great food, and fun activities with lots of local flavor!

When: 
Saturday, July 12, 2025 6-10pm
Saturday, August 9, 2025 6-10pm
Friday, August 29, 2025 6-10pm

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

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

When: 
Saturday, August 30, 2025 9:15pm

Come as You Art

Celebrate the end of summer with a full day of artmaking at Cape Ann Museum in Gloucester Massachusetts

Celebrate the end of summer with a full day of artmaking! Try out a new technique, find inspiration around the CAM Green campus, and celebrate the process of creating a work of art. Crafting stations will be set up outside and in the Carlson Education Center for visitors of all ages to explore. Make a zine, room décor, card, or gift, or just try your hand at practicing with a new artistic medium. A variety of materials will be available throughout the day while supplies last.

When: 
Saturday, August 16, 2025 10am-4pm
Location: 

Gloucester Waterfront Festival

Come to Stage Fort Park in Gloucester Massachusetts for the Annual Waterfront Festival.

Get ready for a weekend of art, flavor, and seaside charm as the 44th Annual Gloucester Waterfront Festival returns to the historic Stage Fort Park on August 16 & 17, 2025. Set against the stunning backdrop of Gloucester Harbor, this beloved festival invites visitors to explore an extraordinary array of over 200 juried booths featuring American-made arts, crafts, specialty foods, and more! 

When: 
Saturday, August 16, 2025 9am-6pm
Sunday, August 17, 2025 9am-5pm
Location: 

Summer Concert Series at Stage Fort Park

Compaq Big Band is just one of the perfromers in the Summer Concert Series at Stage Fort Park in Gloucester Massachusetts!

Come enjoy a Summer evening sea-side concert at Stage Fort Park in Gloucester Massachusetts! The Cape Ann Community Band under the direction of David Benjamin, plays their annual summer concerts Sundays at the at the Antonio Gentile Bandstand, Stage Fort Park, Hough Avenue, Gloucester MA.

When: 
Sundays, July 6-August 24, 2025 6:30pm
Saturday, August 16, 2025 6:30pm
Location: 

Kids Sail Free on the Schooner Lannon

Kids ride free on the 10:30am an Noon Saturday Cruise on the Schooner Lannon through Summer

Schooner Thomas E. Lannon is a fixture on the Gloucester Harbor vista throughout the day in the warm months, but to really experience the Lannon, you need to come aboard and go for a cruise!  Sail and see lighthouses, castles, scenic beaches, and magnificent waterfront homes.

When: 
Saturdays through July and August 2025, 10:30am or Noon

The Backyard Growcery

Join Backyard Growers at Burnham's Field in Gloucester Massachusetts for a weekly Farmer's Market

Stop by Gloucester’s new weekly farmers market, the Backyard Growcery, managed by Backyard Growers. The Backyard Growcery is located at Burnham's Field, an urban park near Gloucester’s thriving waterfront, and features small-scale North Shore farmers, bakers, a seafood vendor, an artisanal pizza maker, and more, throughout the season.

When: 
Wenesdays, June 18 - October 15, 2025 2:30-6pm
Location: 

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Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich Massachusetts

Valentine's Day

12:00 am to 11:59 pm

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!
7:00 am to 6:00 pm

Boston Bruins Annual Pajama Drive

Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm

LEGO World: Wonderealms

Drop in at LEGO World: Wonderrealms at Wenham Museum in Wenham Massachusetts
This all-new experience invites visitors to explore an extraordinary LEGO world where creativity knows no bounds. From enchanted forests and futuristic skylines to pirate coves and steam-powered frontiers, each realm is packed with intricate details, playful surprises, and clever touches you won’t...
9:00 am to 4:00 pm

The Merrimack River Eagle Festival

Come celebrate the return of the Eagles to the Merrimack Estuary! Photo: Eagle on Ice by Bill O'Connor
When winter returns to the lower Merrimack Valley, so do Bald Eagles and Snowy Owls and other exciting winter wildlife. Every year Mass Audubon hosts a grand event marking their return.  Come to Newburyport on Saturday, February 14, 2026, for a full day of fun indoor and outdoor activities that...
9:00 am to 4:00 pm

StoryWalk at Halibut Point

StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
10:00 am to 2:00 pm

February Vacation at MIT Museum

Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Quarry Quest Treasure Hunt

Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
10:00 am to 2:00 pm

Discover Saturdays at Cape Ann Museum

Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
10:00 am to 12:00 pm

CAM Kids: Be Mine Valentine

CAM Valentine Workshop for kids at Sawyer Free Library  in Gloucester Massachusetts
Drop into the Teen Room at the Sawyer Free Library for a Valentine’s Day card-making activity inspired by the Folly Cove Designers.
10:30 am to 1:00 pm

Maple Stroll at Appleton Farms

Appleton Farms has their own sugar maple syrup production facilities to service their abundant suplly from their many sugar maples
Visit the historic maple stand and sugar shack at Appleton Farms and learn all about maple sugaring, its history at the farm and in New England, and how you can try your hand at it at home!
11:00 am to 2:15 pm

Tuesday, February 17

February Vacation Week at Appleton Farms

Appleton Farm's February Vacation Week Program is perfect for kids who want to explore the winterscapes of our extensive property!
In the winter, many people hunker down to stay indoors, but at Appleton Farms, we make the most of the cold, quiet season. There is no better place to spend winter farm days than in exploring in the snow and learning to love the outdoors in all seasons! This program is for kids who are looking to...
9:00 am to 3:00 pm

Quarry Quest Treasure Hunt

Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
10:00 am to 2:00 pm

StoryWalk at Halibut Point

StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
10:00 am to 2:00 pm

February Vacation at MIT Museum

Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm

Bruins PJ Pep Rally

Dome to Sawyer Free Library in Gloucester Massachusetts for a Boston Bruins PJ Pep Rally!
Boston Bruins Mascot Blades is coming to The Sawyer Free Library, Gloucester to get the community involved in the Boston Bruins Annual Pajama Drive to benefit DCF Kids and Cradles to Crayons.
2:00 pm to 3:30 pm

Chess Club at Salem Public Library

Salem Public Library hosts a weekly chess club for all ages on Tuesday evenings.
Salem Public Library the library is hosting weekly chess nights where players of all ages can play and learn from each other.  Whether you're new to the game or a veteran player, all skill levels welcome, and basic instruction
6:30 pm to 7:30 pm

Wednesday, February 18

Boston Bruins Annual Pajama Drive

Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm

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!
7:00 am to 6:00 pm

February Vacation Programs for Kids at Danvers YMCA

February vacation week programs at the Danvers YMCA in Massachusetts
Looking for fun plans during February vacation week? The Danvers YMCA is hosting Vacation Break Adventures from February 16–20, offering a full week of engaging, hands-on activities for kids. There are themed days full of arts & crafts, science fun, gym games, swimming, and more. Highlights...
9:00 am to 4:00 pm

February Vacation Week at Appleton Farms

Appleton Farm's February Vacation Week Program is perfect for kids who want to explore the winterscapes of our extensive property!
In the winter, many people hunker down to stay indoors, but at Appleton Farms, we make the most of the cold, quiet season. There is no better place to spend winter farm days than in exploring in the snow and learning to love the outdoors in all seasons! This program is for kids who are looking to...
9:00 am to 3:00 pm
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