Gloucester

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

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

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

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

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

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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Brookwood School Summer Program for kids Pre-K through 9 in Manchester Massachusetts

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

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

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

CraneOutdoors: Family Snowy Owl Prowl

Join the Trustees of Reservations at the Crane Wildlife Refuge in Ipswich Massachusetts in search of the Snowy Owl!
Wide-open coastal sites are the location of choice for wintering Snowy Owls; common perches are dunes and salt hay staddles. In winters past, these owls have been frequent visitors to the Crane Wildlife Refuge.
10:00 am to 12:00 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

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

Santa's Workshop

Santa's Workshop in Newburyport, Massachusetts. Visit Newburyport MA during the holidays
Newburyport is a favorite local town to shop - especially during the holidays. The fantastic lights downtown, the tree in Market Square, all the beautifully decorated window boxes and of course, Santa's Workshop, where the kids can whisper their wishes to Santa.
11:00 am to 2:00 pm

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

CraneOutdoors: Winter Solstice Hike and Fire Pit Adventure

Hike to Cedar Point at the Crane Wildlife Refuge with the Trustees of Reservations in Ipswivch Massachusetts.
Join us for a beautiful hike to Cedar Point to celebrate the Winter Solstice! Winter at the Crane Estate has much to offer, and while just about everybody on the North Shore has probably been to Crane Beach, Cedar Point is a much less-explored part of the property. Offering maritime scrub forest,...
2:00 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

A Winter Solstice Celebration at Harold Parker

Come celebrate the longest night - Winter Solstice - at Harold Parker State Forest
What causes the winter solstice, and what does it mean for us? Come to Harold Parker State Forest and discover this most important day of the year to ancient peoples and also to ourselves. Join us for a cup of hot chocolate! We will celebrate the solstice at sunset at exactly 4:14 pm and usher out...
3:00 pm to 5:00 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

Rockport's Annual Christmas Pageant

The Rockport Christmas Pageant is a wonderful tradition hosted by the Rockport A
Come to downtown Rockport Ma for a torch-lit live reenactment of the Nativity - a long standing community tradition in Rockport Massachusetts! Each year hundreds of spectators gather to watch the live re-enactment of the story of baby Jesus, Mary and Joseph, the Bethlehem inn and the stable. The...
5:00 pm

Sunday, December 22

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

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

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

CraneOutdoors: Sunday Family Snowy Owl Prowl

Join the Trustees of Reservations at dlife Refuge in Ipswich Massachusetts in search of the Snowy Owl!
Wide-open coastal sites are the location of choice for wintering Snowy Owls; common perches are dunes and salt hay staddles. In winters past, these owls have been frequent visitors to the Crane Wildlife Refuge.
1:00 pm to 3:00 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

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

Monday, December 23

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

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
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