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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Saugus Iron Works Park Grounds & Estuary Walk

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

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Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .

Where: Pingree School

8:00 am to 6:00 pm

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Crescent Farm Corn Maze

Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...

Where: Crescent Farm

9:00 am to 9:00 pm

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Salem Witch Hunt Walking Tour

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

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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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Saturday, October 18

Haunted Happenings Marketplace

The Haunted Happenings Merchant Marketplace is coming this October! Get ready for a one-of-a-kind shopping extravaganza throughout Historic (and some say haunted) Downtown Salem!

Where: Downtown Salem, Where: Salem Common, Where: Derby Square

10:00 am to 6:00 pm

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Ipswich Illumination

The Town of Ipswich, Massachusetts, proudly presents 2025 Ipswich Illumination. This year we are celebrating harvest, hearth, & home, and our maritime history, heritage & culture.

Where: Downtown Ipswich

11:00 am to 9:30 pm

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Saugus Iron Works House Tours

Join National Park staff at Saugus Iron Works National Historic Site for a 30-minute tour of The Iron Works House.

Where: Saugus Iron Works National Historic Site

11:00 am

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Georgia Made This: Scavenger Coin Hunt

Georgia's seventh annual Salem Gold Coin Hunt returns this October, courtesy of the Peabody Essex Museum! Each Saturday and Sunday throughout October, Georgia will release special clues at 12 noon through her Instagram page and the PEM's Instagram story. Those clues will help coin hunters narrow...

Where: Peabody Essex Museum

12:00 pm to 7:00 pm

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Saugus Iron Works Tours

Join the National Park staff at Saugus Iron Works National Historic Site for a tour of the colonial industrial site. On select days, you may be able to stick around and witness pop-up molten iron pour, blacksmithing, waterwheel demonstrations, and take part in hands-on river stewardship activities.

Where: Saugus Iron Works National Historic Site

2:00 pm

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Low-Sensory Play at North Shore Children's Museum

Join us for a low-sensory play session. For some children, visiting places like NSCM can be over-stimulating. This special play session will have reduced noise, crowds, and stimulation. While medical diagnosis is not required, we encourage that these limited tickets be used for families with a...

Where: North Shore Children's Museum

2:00 pm to 4:00 pm

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Halloween on the Hill

The Trustees of Reservations invite you to tour the gardens at Long Hill Gardens in Beverly, Massachusetts to celebrate Autumn and Halloween! Long Hill is excited to bring back our annual Halloween on the Hill event! Come explore our beautiful property as we transform the Long Hill gardens into a...

Where: Long Hill and Sedgwick Gardens

5:00 pm to 8:30 pm

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Sunday, October 19

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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