Gloucester

Annual Pizza Taste Off

The annual pizza taste-off in Gloucester raises funds for the American Cancer Society

The Interact Club at Gloucester High School will be holding their annual pizza taste off at Cruiseport Gloucester!  Come try different pizza from around Cape Ann, while helping to raise funds for the American Cancer Society! Taste them all for yourself and vote for the best! Only 300 tickets sold and will be available at the door. All proceeds will be donated to the American Cancer Society.

When: 
Wednesday, April 8, 2026 5-7pm

Gloucester Education Foundation's Power of Play Festival

Gloucester Education Foundation is proud to host Power of Play Festival, a day of play for Gloucester Massachusetts families and kids of all ages. Gloucester Education Foundation's Power of Play Festival

Gloucester Education Foundation hosts the annual Power of Play Festival in Gloucester Massachusetts. GEF’s annual “Day of Play” is back for an 8th year on Sunday, March 22! This FREE community event draws hundreds of Gloucester families to the GHS Field House to participate in dozens of fun activities, led by community volunteers and partners. Check out photos below from past years by community volunteer Marty Del Vecchio and GHS student photographers, and this video by 1623 Studios! Together, they will give you a taste for this beloved event.

When: 
Sunday, March 22, 2026 11am-2pm

Cape Ann Symphony | Moods of the Sea

Combining music, literature and poety, this concert is sure to please everyone. Moods of the Sea captures the stylistic choices of these works, with undercurrents and rippling chords. An superb program that hints at motifs from folk traditions that expand to create full movements of beautiful sounds. You won't want to miss this one!

When: 
Sunday, February 8, 2026 3pm

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. Members of the Cape Ann Museum’s CAM Teen Council will be there to guide you in this hands‑on activity, where you can learn about the Designers’ beautiful artwork inspired by life on Cape Ann and try your own block‑printing using foam shapes and a pencil. Create unique, handmade cards just in time for Valentine’s Day!

When: 
Saturday, February 14, 2026 10:30am-1pm
Location: 

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 and organizations can register to host their own drive and fans are encouraged to help by purchasing a donation from Cradles to Crayons' Amazon Wishlist.

When: 
February 1 - March 15, 2026

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. The PJ Drive’s goal is to collect 10,000 pairs of new pajamas for children and teens in need.  

When: 
Tuesday, February 17, 2026 2-3:30pm

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.

When: 
Saturday, January 24, 2026 10am-Noon

Gloucester's So Salty 2026

Celebrate Gloucester Massachusetts recognizably salty character with local cultural institutions in the heart of downtown.

Celebrate the fish city’s recognizably salty character with local cultural institutions and businesses during the 5th Annual Gloucester’s So Salty festival sponsored by the Cape Ann Museum in partnership with Discover Gloucester! This annual event brings over 2,000 people to the downtown area each January to shop at local stores, enjoy family friendly activities, visit the Museum Courtyard, and find each of the ice sculptures sponsored by local cultural institutions and businesses.

When: 
Saturday, January 24, 2026 10am-4pm
Sunday, January 25, 2026 10am-4pm

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 own unique holiday theme. From nature’s bounty of fruits and greenery to the warm glow of candlelight, every detail creates a true feast for the senses. Along the way, you will encounter a royal guard of nutcrackers standing watch over a gingerbread house replica of the castle. Keep an eye out for playful elves and gnomes who are up to mischief—great fun for little ones! This year, the celebration will also shine with the glow of two menorahs on display, honoring the traditions of Hanukkah within the Museum’s holiday splendor.

When: 
Daily November 21 - January 4, 2025 Times Vary
Closed Christmas Eve and Day, New Year's Eve and Day

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Appleton Farms in Ipswich Massachusetts offers farm-based Summer Programs for kids ages 5-15

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

Barnyard Story Hour at Appleton Farms

Kids can meet the barnyard animals and hear a story at Appleton Farms in Ipswich Massachusetts.
Bring your little ones to Appleton Farms for our farm-fresh story hour. We will read books about animals and nature, maybe sing a song or two, then head up to the carriage barn to visit our Nubian goats, Angora rabbits and see what other animals are out and about on the farm. We will engage in...
10:30 am to 11:30 am

Wednesday, April 8

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

Annual Pizza Taste Off

The annual pizza taste-off in Gloucester raises funds for the American Cancer Society
The Interact Club at Gloucester High School will be holding their annual pizza taste off at Cruiseport Gloucester!  Come try different pizza from around Cape Ann, while helping to raise funds for the
5:00 pm to 7:00 pm

Stargazing at Mendel Observatory

Mendel Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night
The Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night (weather permitting) starting at dusk or 7:30 pm, whichever is later.  When special astronomical events of interest occur (total lunar eclipses, etc.) the Obs
7:00 pm

Thursday, April 9

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

Friday, April 10

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

Saturday, April 11

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

Teen Naturalist Club at IRWS: Spring/Summer Series

Join Mass Audubon for their Teen Naturalist Club at Ipswich River Wildlife Sanctuary in Topsfield Massachusetts!
Explore a variety of local ecosystems such as a salt marsh, a freshwater river, or a tide pool on the beach. Take part in wildlife data collection in tide pools and vernal pools and engage in conservation projects such as a macroinvertebrate study or a horseshoe crab count in this exciting science...
8:00 am to 5:00 pm

Read to a Dog at SPL

Kids are invited to read to a therapy dog at the Salem Public Library in Massachusetts
Have a new or struggling reader who needs to build confidence and practice reading aloud?  Come read to Hendrix, the trained therapy dog, a sweet a non-judgmental listener!  Bring your own book to read, or choose one of ours.
10:00 am to 11:00 am

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

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
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