Holiday

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts

Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its own unique holiday theme. From nature’s bounty of fruits and greenery to the warm glow of candlelight, every detail creates a true feast for the senses. Along the way, you will encounter a royal guard of nutcrackers standing watch over a gingerbread house replica of the castle. Keep an eye out for playful elves and gnomes who are up to mischief—great fun for little ones! This year, the celebration will also shine with the glow of two menorahs on display, honoring the traditions of Hanukkah within the Museum’s holiday splendor.

When: 
Daily November 21 - January 4, 2025 Times Vary
Closed Christmas Eve and Day, New Year's Eve and Day
Location: 
Hammond Castle Museum
Gloucester
Holiday
Christmas
Decor
Decorating
Museum

Newburyport Holiday House Tour 2025

Newburyport Holiday House Tour hosted by the Newburyport PTO Kitchen Tour

Enjoy touring private residences and unique spaces throughout Greater Newburyport, all decorated in holiday style both inside and out. Your self-guide tour will lead you through each of our homes all decked out both inside and out in holiday style reflecting the homeowner’s individual celebrations and traditions of the season. Come and experience a day full of holiday magic and surprise! Note: This tour is appropriate for children ages 12 and up.

When: 
Saturday, December 13, 2025 9:30am-4pm
Location: 
Downtown Newburyport
Newburyport
Tour
Fundraiser
Charity
Decorating
Decor
Holiday
Design

Ipswich Jingle Bell Walk

Join friends and family for a day of holiday festivities and cheer! Sing carols with Buddy the Elf while waiting for Santa’s arrival.

Get ready for a day full of holiday magic and cheer! Join us at the Ipswich Town Wharf to welcome Santa as he makes his grand entrance. Sing along to festive carols with Buddy the Elf while we wait for the big moment! You can even buy your own jingle bells to ring as we follow Santa and Buddy on a merry “Jingle Bell Walk” to Ipswich Town Hall (45 Green Street). Keep your eyes peeled for a sneaky appearance from the Grinch!

When: 
Saturday, December 13, 2025 11-1pm
Location: 
Downtown Ipswich
South Village Green Ipswich
Ipswich
Food
Holiday
Christmas
Santa
Christmas Walk
Pictures with Santa
Photos

Middle Street Walk Gingerbread Contest 2025

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 prior to the start of the Middle Street at 10am. 

When: 
Saturday, December 13, 2025 10am - 3pm
Location: 
Sawyer Free Library
Gloucester
Holiday
Food
Contest
Competition
Fundraiser
Crafts
Middle Street Walk

The Nutcracker Panto

Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!

Theater in the Open is happy to be back at the Firehouse for our production of A Nutcracker Panto, written by Edward F. Speck and adapted from the classic holiday ballet. Presented in the traditional British panto style, this holiday send-up is a family friendly romp through Clara’s adventure with the Nutcracker, the battle with the Rat King, and more than likely a Tik Tok dance trend. Holiday Pantos with Theater in the Open are a tradition in Newburyport, and we are excited to bring this incredible joy to our community. Join us!

When: 
Fridays, December 12 & 19, 2025 7pm
Saturdays, December 13 & 20, 2025 7pm
Location: 
Firehouse Center for the Arts
Newburyport
Holiday
Performance
Live Performance
Comedy

The Musary presents A Charlie Brown Christmas

The Musary performs A Charlie Brown Christmas at the The Community House in Hamilton Massachusetts

The Musary brings Charlie Brown's Christmas to The Community House! We are absolutely thrilled to welcome you back to one of our most cherished traditions— Charlie Brown Christmas! Join for a magical concert featuring the Aidan Scrimgeour Trio as they Vince Guaraldi’s beloved holiday soundtrack to life (it’s John’s favorite!).

When: 
Saturday, December 13, 2025 3pm
Location: 
Community House Of Hamilton & Wenham
Hamilton
Concert
Holiday
Music
Live Music

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 7, 2025 3pm
Parade participants line up at 2pm on the State Fish Pier
Location: 
Downtown Gloucester
Gloucester
Holiday
Christmas
Parade
Santa
Tree Lighting

Cape Ann Makers Holiday Market

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

Cruiseport Gloucester hosts the Cape Ann Makers Holiday Market. Come get your Christmas and Holiday shopping done while you sip a beverage, listen to music and buy from over 55 local vendors – food gifts, soaps, lotions, artwork, jewelry, home goods, all unique handcrafted items – something for everyone on your list!

When: 
Saturday, November 29, 2025 10am-4pm
Location: 
Cruiseport Gloucester
Gloucester
Shopping
Holiday
Market
Maker
Maker's Market
Gifts
Vendors
Crafts

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 is available for download at this link.

When: 
Saturday, December 13, 2025 9am - 5pm
Location: 
Downtown Gloucester
Gloucester
Holiday
Walk
Food
Performance
Museum
Dance
Santa
Live Performance
Exhibit
Library
Crafts
Art
Tree Lighting
Middle Street Walk

Pages

Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich Massachusetts

Valentine's Day
12:00 am to 11:59 pm
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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!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm
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LEGO World: Wonderealms
Drop in at LEGO World: Wonderrealms at Wenham Museum in Wenham Massachusetts
This all-new experience invites visitors to explore an extraordinary LEGO world where creativity knows no bounds. From enchanted forests and futuristic skylines to pirate coves and steam-powered frontiers, each realm is packed with intricate details, playful surprises, and clever touches you won’t...
Where: Wenham Museum
9:00 am to 4:00 pm
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The Merrimack River Eagle Festival
Come celebrate the return of the Eagles to the Merrimack Estuary! Photo: Eagle on Ice by Bill O'Connor
When winter returns to the lower Merrimack Valley, so do Bald Eagles and Snowy Owls and other exciting winter wildlife. Every year Mass Audubon hosts a grand event marking their return.  Come to Newburyport on Saturday, February 14, 2026, for a full day of fun indoor and outdoor activities that...
Where: Joppa Flats Education Center, Where: Parker River National Wildlife Refuge, Where: Downtown Newburyport
9:00 am to 4:00 pm
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StoryWalk at Halibut Point
StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
Where: Maudslay State Park
10:00 am to 2:00 pm
♦ Read More →

February Vacation at MIT Museum
Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm
♦ Read More →

CraneOutdoors: The Castle Hill Hike
CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
Where: Castle Hill on the Crane Estate
10:00 am to 12:00 pm
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Quarry Quest Treasure Hunt
Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
Where: Halibut Point State Park
10:00 am to 2:00 pm
♦ Read More →

Discover Saturdays at Cape Ann Museum
Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
Where: Cape Ann Museum Green
10:00 am to 12:00 pm
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CAM Kids: Be Mine Valentine
CAM Valentine Workshop for kids at Sawyer Free Library in Gloucester Massachusetts
Drop into the Teen Room at the Sawyer Free Library for a Valentine’s Day card-making activity inspired by the Folly Cove Designers.
Where: Cape Ann Museum
10:30 am to 1:00 pm
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Maple Stroll at Appleton Farms
Appleton Farms has their own sugar maple syrup production facilities to service their abundant suplly from their many sugar maples
Visit the historic maple stand and sugar shack at Appleton Farms and learn all about maple sugaring, its history at the farm and in New England, and how you can try your hand at it at home!
Where: Appleton Farms
11:00 am to 2:15 pm
♦ Read More →

Monday, February 16

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm
♦ Read More →

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!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

February Vacation Programs for Kids at Danvers YMCA
February vacation week programs at the Danvers YMCA in Massachusetts
Looking for fun plans during February vacation week? The Danvers YMCA is hosting Vacation Break Adventures from February 16–20, offering a full week of engaging, hands-on activities for kids. There are themed days full of arts & crafts, science fun, gym games, swimming, and more. Highlights...
Where: Danvers Community YMCA
9:00 am to 4:00 pm
♦ Read More →

February Vacation Week at Appleton Farms
Appleton Farm's February Vacation Week Program is perfect for kids who want to explore the winterscapes of our extensive property!
In the winter, many people hunker down to stay indoors, but at Appleton Farms, we make the most of the cold, quiet season. There is no better place to spend winter farm days than in exploring in the snow and learning to love the outdoors in all seasons! This program is for kids who are looking to...
Where: Appleton Farms
9:00 am to 3:00 pm
♦ Read More →

Quarry Quest Treasure Hunt
Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
Where: Halibut Point State Park
10:00 am to 2:00 pm
♦ Read More →

StoryWalk at Halibut Point
StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
Where: Maudslay State Park
10:00 am to 2:00 pm
♦ Read More →

February Vacation at MIT Museum
Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm
♦ Read More →

Tuesday, February 17

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm
♦ Read More →

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!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

February Vacation Programs for Kids at Danvers YMCA
February vacation week programs at the Danvers YMCA in Massachusetts
Looking for fun plans during February vacation week? The Danvers YMCA is hosting Vacation Break Adventures from February 16–20, offering a full week of engaging, hands-on activities for kids. There are themed days full of arts & crafts, science fun, gym games, swimming, and more. Highlights...
Where: Danvers Community YMCA
9:00 am to 4:00 pm
♦ Read More →
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