Gloucester

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

Winter Solstice Hike | Ward Reservation

Come for a solstice hike at Ward Reservation to celebrate the Winter Solstice in North Andover Massachusetts

The Explore! North Shore hiking series will get you outside and moving at some lesser explored Trustees properties across the Northeast Region, at the right time of year to see these special places shine. These beginner hikes will not be too strenuous, and will offer frequent stops for learning and taking in the beauty of our special places.

When: 
Sunday, December 21, 2025 1-3:30pm
Location: 

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, November 30, 2025 3pm
Parade participants line up at 2pm on the State Fish Pier

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

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

The Open Door Autumn Breakfast

The Open Door Autumn Breakfast is a fundraiser that helps families in need on the North Shore

Cruiseport Gloucester and The Open Door invite you to a celebration of community spirit! Each year, The Open Door Autumn Breakfast kicks off the holiday giving season and raises funds for Holiday Meal Baskets (and beyond). Each basket provides local people with all the ingredients they will need to make a special meal, and Holiday Baskets are available for BOTH Thanksgiving and the winter holidays. LIMITED SPOTS AVAILABLE, purchase tickets in advance to guarantee your spot.

When: 
Wednesday, October 22, 2025 7:30-9am
Location: 

Farmers Markets on the North Shore

You'll find locally grown food and much more at farmers markets on the North Shore, north of Boston Massachusetts.

The North Shore of Massachusetts, renowned for its fertile soil, is home to farms that produce an abundance of fresh, delicious foods. These can be purchased directly from the farms or at the local farmer's markets, where the experience is more than just shopping—it's about community. On a sunny Saturday morning, families can explore these vibrant markets, filled with colorful produce, homemade jams, fresh bread, and artisanal crafts.

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

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
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....
9:00 am to 5:00 pm

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...
10:00 am to 8:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
10:00 am

SeaFestival of Trees in Salisbury | Saturdays

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

SeaFestival of Trees in Salisbury

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

Greet Santa at the Hawthorne Hotel

Salem Main Streets, SalemMainStreets.org, Visit Salem MA for the holidays
Join Salem Main Streets and the City of Salem as we celebrate two of our most beloved annual traditions – Santa’s Arrival and the lighting of Salem’s Holiday Tree – all in one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00 p.m. on Friday...
5:45 pm to 8:00 pm

Salem Holiday Tree Lighting

Come to the Holiday Tree Lighting in Salem to kick off the holiday season!
Join Salem Main Streets and the City of Salem as we combine two of our most beloved annual traditions – Greet Santa at the Hawthorne Hotel and the lighting of Salem’s Holiday Tree – into one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00...
5:45 pm to 6:30 pm

Beverly Tree Lighting

Beverly Massachusetts holiday tree lighting on the Common is a favorite community event!
Come to the Beverly Tree Lighting!  Gather with your neighbors and enjoy cocoa, cookies, music and Santa, as we light the town Holiday Tree!
7:00 pm

Saturday, November 29

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

Thanks for the Trails 5k

ECGA's Thanks for the Trails 5k Race on the Friday after Thanksgiving in Patton Park
ECTA is holding its 8th Annual Thanks for the Trails 5k and Kids Fun Run the Saturday after Thanksgiving at Patton Park in Hamilton (November 29, 2025).  The Kids' Run will begin at 9:30AM and the 5k will start at 10AM.  Using a scenic and challenging course and offering great prizes, this will be...
7:30 am to 11:30 am

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
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....
9:00 am to 5:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
10:00 am

Bevrec Toy Drive

Beverly Massachusetts Recreation Department hosts a holiday toy drive at Lynch Park!
The BevRec will be hosting a Holiday Toy Drive at Lynch Park to benefit the great work that Beverly Bootstraps does for our community. We’re collecting new, unwrapped toys for children of all ages to help make this season brighter for everyone in our community.
Where: Lynch Park
10:00 am to 1:00 pm

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...
10:00 am to 8:00 pm

SeaFestival of Trees in Salisbury | Saturdays

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
2:00 pm to 9:30 pm
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