Gloucester

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

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

Middle Street Walk in Gloucester

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

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 in Gloucester.

When: 
Saturday, December 14, 2024 10am-7pm

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts

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

Cape Ann Makers Holiday Market

Cape Ann Makers Holiday Market held at Cruiseport in Gloucester Massachusetts.

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

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

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

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

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Art Academy Summer Program at Montserrat College of Art in Beverly MA

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 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

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
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...
10:00 am to 4:00 pm

A Colorful Christmas at Castle Hill

A Colorful Christmas by the Sea is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s Travels with the Cranes. Each room in our 1920s mansion is decorated for the holidays drawing inspiration from Crane travels around the world, including Paris, Japan, Egypt, and New York.
10:00 am to 8:00 pm

Music Together - Friday

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
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...
10:30 am to 11:15 am

Gingerbread Contest at Wenham Museum

Wenham Museum Gingerbread Contest is free to enter and open to all!
Everyone's invited to enter Wenham Museum’s gingerbread contest! Individuals, families, groups, teams–all are encouraged to create a Gingerbread House for this friendly community competition.
12:00 pm to 4:00 pm

A Christmas Carol Panto

Theater in the Open celebrates the holidays with their interpretation of Dickens' Christmas Carol at the Firehouse Center for the Arts in Newburyport!
Bah, humbug! Theater in the Open celebrates the holiday season with this Dickens classic, presented in true TITO style. So be prepared for anything to happen!  
3:00 pm to 9:00 pm

Beverly Downtown Winter Market

Beverly Downtown Winter Market is a weekend full of holiday fun, music, food and shopping in Beverly Massachusetts
Come to Beverly Massachusetts for two festive evenings of holiday cheer during Cabot Night (Friday, 12/13) and Rantoul Night (Saturday, 12/14)! Both nights are packed with activities for all ages, including local shopping, live music, and delicious treats. Don’t miss the Beverly Memory Tree...
4:00 pm to 8:00 pm

Trustees Winterlights at Stevens Coolidge Place

The Trustees of Reservations Winterlights at the Stevents-Coolidge Place North Andover North Andover.
Winterlights is back! Join the Trustees for a magical outdoor experience at Stevens-Coolidge House & Gardens, and see the gardens aglow with your favorite light installations as well as marveling at new components. Bring the whole family for a fun and safe outdoor experience. Winterlights runs...
4:30 pm to 8:00 pm

Holiday Invitation Nights

Downtown Newburyport Massachusetts is the place to shop during the invitation nights!
Come to Downtown Newburyport, Tannery Marketplace  and the Merrimac Placefor Newburyport’s Holiday Invitation Nights and shop for the holidays in style! Mark your calendars, book a babysitter, and call your friends to make plans for three great nights in Newburyport! Enjoy merchant hospitality,...
6:00 pm to 9:00 pm

Saturday, December 14

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 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

Breakfast with Santa

Kids will enjoy breakfast with Santa at the Hamilton Wenham Community House
Come and enjoy a continental style breakfast and get your picture taken with Santa. We will also have a letter writing station and music entertainment. Following the event at 3 pm, the Musary will be sponsoring a FREE Holiday concert! Donations to The Musary will be welcome. We hope to see you!...
7:30 am to 1:30 pm

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.
9:00 am to 5:00 pm

Music Together - Saturday

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
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...
9:15 am to 11:15 am

A Colorful Christmas at Castle Hill

A Colorful Christmas by the Sea is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s Travels with the Cranes. Each room in our 1920s mansion is decorated for the holidays drawing inspiration from Crane travels around the world, including Paris, Japan, Egypt, and New York.
10:00 am to 8:00 pm

Sing & Dance with the Music Man

Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
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,...
10:00 am to 10:45 am

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...
10:00 am to 3:00 pm

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!
10:00 am to 7:00 pm

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
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...
10:00 am to 4:00 pm
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