Gloucester

Deck The Halls: Hammond Castle

Come to Hammond Castle for the 6th annual Deck The Halls holiday celebration. Hammond Castle Museum will be dressed for the holidays inside and out. Delight in the enchanting ambiance of Christmas and White Birch trees, meticulously arranged garlands, festive wreaths, and the warm embrace of candlelight that will envelop you throughout your tour of the Hammond Castle Museum. Immerse yourself in a bygone era of opulent tranquility and holiday grandeur that promises to be unlike any other experience on the North Shore.

When:

Daily November 21 - Decemeber 28, 2024 10am-4pm

Location:

Hammond Castle Museum

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Santa at Sea Cruise

Sail with Santa aboard the Beauport Princess on the water of Gloucester Harbor in Massachusetts

Enjoy a holiday harbor cruise aboard Beauport Cruiselines with Santa! Take in the beautiful views of Gloucester Harbor, all while singing holiday carols with elves, enjoying hot cocoa and cookies, and listening to a reading of “The Night Before Christmas.” Plus, a visit from Santa himself! Tickets include hot cocoa, cookies, and a picture with Santa. A Cash bar will be available. Two 90 Minute cruises are offered.

When:

Sunday, December 15, 2024 11am or 2pm

Location:

Cruiseport Gloucester

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Deck the Docks at Maritime Gloucester

Deck the Docks at on the Gloucester Massachusetts Waterfront and join the holiday cheer!

Come to Maritime Gloucester for fun holiday happenings on the waterfront in Gloucester Massachusetts! Find unique maritime themed gifts and stick around for kids events including kids holiday crafts with Cape Ann Art Haven, free hot cocoa, story time in the classroom, Musical Performance by The Gloucester Student Band, Santa's arrival by schooner and more during Gloucester's Middle Street Walk 2024.

When:

Saturday, December 14, 2024 10am-7pm

Location:

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Middle Street Walk 2024

The lighting of the Lobster Trap Tree is part of Middle Street Walk's finale in Gloucester Massachusetts.

The Annual Middle Street Walk is a great way to experience Gloucester's Historic District and waterfront while having Holiday fun with the family. An updated schedule of this years walk will be available for download on December 1, 2024 at this link.

When:

Saturday, December 14, 2024 9am - 5pm

Location:

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Middle Street Walk Gingerbread Contest 2024

Middle Street Walk Gingerbread Contest entries can take any shape.

Everybody is invited to enter the Gingerbread Contest for the Middle Street Walk in Gloucester this year! Groups and individuals are encouraged to get creative and come up with entries that can take any shape. All entries will be judged during the Middle Street walk with winners being announced at 1pm in Gloucester City Hall.

When:

Saturday, December 14, 2024 10am - 3pm

Location:

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ECGA Mutt Strut

Hike Thompson Street Reservation in Gloucester Massachusetts with your dog and the ECGA!

An adventurous outing for you and your pup! Tompson Street has a little of everything: wooded trails, bridges across the swamp, rocky outcroppings…! The dogs and humans have a blast! Social dogs very, very welcome!

When:

Sunday, December 8, 2024 1:30-3:30pm

Location:

Thompson Street Reservation

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Cape Ann Makers Holiday Market

Come to Cruiseport Gloucester to the Cape Ann Makers Holiday Market. Support your local economy and makers by shopping local. Saturday, November 24, 2023, is Small Business Saturday. When shopping local please come by to Cruiseport Gloucester for the Holiday Sip and Shop Market.

When:

Sunday, December 1, 2024 10am-4pm

Location:

Cruiseport Gloucester

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Renaissance Faire Day

Return to the Renaissance on the oceanside lawn at Hammond Castle in Gloucester Massachusetts

Step back in time at our Renaissance Faire Day! Immerse yourself in the enchanting world of medieval and Renaissance culture with live performances by The Harper & The Minstrel and the L.I.A.R.S. (Ladies of Integrity, Aristocracy, Repute, and Society), offering a mesmerizing blend of medieval, Renaissance, and Celtic music as they stroll through the Museum and grounds.

When:

Saturday, November 9, 2024 10am-6pm

Location:

Hammond Castle Museum

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Fishtown Horribles Parade of Trees

Fishtown Horribles Parade Trees, a holiday fundraiser in Gloucester Massachusetts

Gloucester's Fishtown Parade of of Trees is a community holiday fundraiser for the annual Fishtown Horribles Parade in July! Take a stroll the the Parade of Trees and find your favorites! All trees are donated and decorated by community members, businesses and organizations.

When:

Saturday, December 7, 2024 10am-8pm

Sunday, December 8, 2024 11am-5pm

Location:

First Baptist Church of Gloucester

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Gloucester's Santa Parade & Tree Lighting

Santa will come to Gloucester to launch the Christmas Parade and Tree Lighting -

Gloucester's Holiday Parade is a great tradition to kick off the holidays! Come enjoy the parade, Santa, and the tree lighting at Kent Circle! Volunteers will line up parade participants at the State Fish Pier on Parker Street at 2:00 PM and will guide them through downtown Gloucester and on to Kent Circle for the Annual Tree Lighting Ceremony.

When:

Sunday, December 1, 2024 3pm

Parade participants line up at 2pm on the State Fish Pier

Location:

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Maudslay in Bloom Self-Guided Walk

Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...

Where: Maudslay State Park

7:00 am to 7:00 pm

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Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Take a self guided tour at one of Massachusetts most beautiful locations!

Where: Halibut Point State Park

7:00 am to 6:00 pm

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Beverly Library Spring Book Sale

Our annual Friends' Spring Book Sale takes place daily at the main library from Saturday, Saturday May 10 through May 17. The sale will be open daily during regular library hours: Mon.-Thurs., 9AM-9PM; Fri.

9:00 am to 5:00 pm

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Music Together - Wednesday

Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45 minutes...

Where: St. John's Episcopal Church in Beverly Farms

9:30 am to 11:15 am

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Swan Boat Rides in Boston Public Garden

The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.

Where: Boston Common and Boston Public Garden

10:00 am to 4:00 pm

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Sing & Dance with the Music Man

Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday and Saturday mornings at 10am for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician,...

Where: Community House Of Hamilton & Wenham

10:00 am to 10:45 am

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D&D (Ages 10-14) at Amesbury Library

Come play in a Dungeons and Dragons ongoing campaign! You'll create your own characters and build the story session to session. Come if you're a beginner or if you know the rules. All are welcome! Registration is required and is for all 7 weeks.

Where: Amesbury Public Library

4:00 pm to 6:00 pm

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Stargazing at Mendel Observatory

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

Where: Mendel Observatory at Merrimack College

7:00 pm

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Saturday, May 17

Music Together - Saturday

Where: Grace Episcopal Church in Salem

9:15 am to 11:15 am

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Swan Boat Rides in Boston Public Garden

Where: Boston Common and Boston Public Garden

10:00 am to 4:00 pm

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Salamander Meander

We'll search the sanctuary's vernal pools, ponds, and woodlands for a variety of amphibians that are the on the move. If we're lucky, we might see Wood Frog and Spotted Salamander eggs and catch a few adults to observe up close and then release.

Where: Ipswich River Wildlife Sanctuary

10:00 am to 2:30 pm

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Birds, Bees & Butterflies | Family Nature Series at Cox Reservation

Essex County Greenbelt Association invites families to Cox Reservation for a fun session that's all about bees! This show-and-tell introduces children of all ages to the importance of bees and other pollinators.

Where: Cox Reservation

10:00 am to 1:00 pm

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Gloucester Student Arts Festival

Arts Fest is an annual celebration of the arts in the Gloucester Public Schools, a day to enjoy creativity, connection, and celebrating our students’ talents as a Gloucester community. It is led by the Gloucester Education Foundation in partnership with the Gloucester Public Schools, Cape Ann...

Where: Cape Ann Museum Green, Where: O'Maley Innovation Middle School

11:00 am to 4:00 pm

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TitO presents Petrushka & the Caterpillar

What happens when your favorite stories need a new ending? Everyone's favorite clown upends iconic fables and fairytales in our signature storytelling style – with tons of imagination, humor, and heart. Join Petrushka and the gang as they retell old stories for our times!

Where: Maudslay State Park

2:00 pm to 4:30 pm

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Sunday, May 18

Todd Farm Market

From early Spring to late Fall, Todd Farm is a great Sunday destination for families! Head to the farm and explore the outdoor award-winning Market featuring up to 240 vendors from all over New England and New York!

Where: Todd Farm Market

5:00 am to 3:00 pm

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Bluefin Blowout Family 5k to Benefit Alzheimer's Association

On Sunday, May 18th, 2025, come to Stage Fort Park, Gloucester for the Bluefin Blowout Family Fun Run 5K, Presented by the Lyon-Waugh Auto Group - Benefiting the Alzheimer’s Association. Run, walk, or stroll from Stage Fort Park to Hammond Castle and back to Stage Fort Park for a 5K loop. Enjoy the...

Where: Stage Fort Park

7:00 am to 10:30 am

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