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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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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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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Gloucester Gratis Days at Hammond Castle

In keeping with John Hays Hammond, Jr's original vision for his seaside castle-home to serve as a museum offering the Gloucester community access to ancient works of architectural art, Hammond Castle Museum will offer Gloucester residents free, self-guided tours each Tuesday throughout the regular...

Where: Hammond Castle Museum

10:00 am to 4:00 pm

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Music Together - Tuesday in Marblehead

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

Where: Unitarian Universalist Church of Marblehead

10:00 am to 10:45 am

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Barnyard Story Hour at Appleton Farms

Barnyard stories really come alive when you get to see the main characters in real life! Bring the kids down to Appleton Farms for our farm-fresh version of story time. Explore the farmstead, visit our learning garden, see our cows and rabbits, and find a spot to play under a shady tree in our...

Where: Appleton Farms

10:30 am to 11:30 am

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Chess Club at Salem Public Library

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

Where: Salem Public Library

6:30 pm to 7:30 pm

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Saturday, May 3

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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Spring Bloom Fest at the Stevens-Coolidge Estate

Join The Trustees of Reservations for the start of Spring at Stevens-Coolidge House & Gardens with a celebration of bulbs at our Spring BloomFest weekend! Stroll through our beautiful gardens with budding tulips, daffodils, and other spring bulbs while enjoying the crisp spring air and...

Where: Stevens-Coolidge House & Gardens

10:00 am to 4:00 pm

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North Shore Nature Fair | Glen Urquhart School

Celebrate nature at GUS with a variety of hands-on activities and nature-based projects led by GUS educators and partners from across the North Shore. This free, family-friendly event, is open to the public.

Where: Glen Urquhart School

1:00 pm to 3:00 pm

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Square-Foot Gardening Workshop

In this workshop, the Backyard Growers team will introduce you to the Square-Foot Gardening Method, which helps gardeners make the most of often limited growing space, and grow the most food possible for a household. We'll show you how to do this by using gridded square-feet instead of rows. You'll...

Where: Backyard Growers Program

9:30 pm to 11:00 pm

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Sunday, May 4

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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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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Step up for Colleen 5k

The friends and family of Colleen Ritzer have created this 5K walk/run to celebrate Colleen’s life and her commitment to help and inspire others. Through the Step Up for Colleen event, organizers hope to enhance a sense of community and overall goodwill as we come together to honor Colleen and the...

Where: The Park at Andover Town Offices

8:30 am

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Tulip Festival at Cider Hill Farm

A gorgeous, fan-favorite variety of 100k tulips are scheduled to bloom in early May. Welcome spring with this multi-weekend festival featuring free live music, self-guided blooming orchard walks, outdoor hard cider bars, food trucks, fitness n' family activities and cut-your-tulips. General...

Where: Cider Hill Farm

8:30 am to 4:30 pm

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Newburyport Farmers' Market

The Newburyport Farmers Summer Market celebrates local fresh produce every Sunday morning rain or shine! Start your Sunday browsing fresh North Shore local produce, meats, cheeses, and seafood in an open air market atmosphere! Food and beverage vendors offer fresh hot coffee, breakfast treats and...

Where: Tannery Marketplace

9:00 am to 1:00 pm

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Gloucester

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Saturday, May 3

Sunday, May 4