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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

Marblehead Christmas Walk

The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts

The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets, Gingerbread Festival, Entertainment & much more! There are all kinds of family events and activities sponsored by local merchants and organizations.

When: 
Thursday, December 4, 2025 - Sunday, December 7, 2025

Annual ECTA Equine Expo & Tack Sale

Essex County Trail Association is hosting the annual Equine EXPO at Topsfield Fairgrounds

Don't miss the 31st annual Equine EXPO & Tack Sale, Saturday, April 25, 2025 from 9-3 in the Arena Building at the Topsfield Fairgrounds on Route 1, Topsfield, MA. Individuals, groups & businesses will make up our booths offering new and used items as well as services for the horse and rider/driver. Vendor spaces are available.

When: 
Saturday, April 25, 2026 9am-3pm

Haunted Biz Baz Street Fair

The Biz Baz Street Fair in Salem Massachusetts hosts dozens of Chamber members and unique vendors selling handmade art, crafts, gifts, apparel, and more.

Come visit the Biz Baz Street Fair to see over 80 vendors and enjoy the historic Salem Common. Vendor sales include handmade jewelry, art, apparel, crafts, Halloween decor and so much more! The Biz Baz will be in the Salem Common and you can shop on Saturday, October 4, from 10AM-6PM, and Sunday, October 5, from 10AM-6PM. This event brings thousands of visitors, so you do not want to miss out! Hosted by the Salem Chamber of Commerce.

When: 
Saturday, October 5, 2024 10am-6pm
Sunday, October 6, 2024 10am-6pm
Location: 

Downtown Gloucester Block Party

Food, music, live entertainment, dance, craft and fun come together for a great

Main Street, Downtown Gloucester Massachusetts comes alive when the Street is closed off to allow live music, street performers, kid activities, non-profits, food vendors and more! Many of shops and businesses on Main Street will be open for business and will welcome partygoers. Other Gloucester businesses and non-profits will be represented on the Street as well. come for a night full of Live music, great food, and fun activities with lots of local flavor!

When: 
Saturday, July 12, 2025 6-10pm
Saturday, August 9, 2025 6-10pm
Friday, August 29, 2025 6-10pm

Ipswich Downtown Tuesdays

Ipswich Downtown Tuesdays includes great dining live music, dancing & extended shopping hours for shopping Downtown Ipswich Massachusetts Tuesday evenings!

Ipswich Downtown Tuesdays includes great dining, live music, dancing at the Take-Out Terrace Stage on the Riverwalk  & extended shopping hours for shopping Downtown Ipswich Tuesday evenings!  Each week will feature live entertainment on the Riverwalk, making for a fun evening out for the whole family!

When: 
Tuesdays, July 1 - August 26, 2025 6-8PM

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Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury 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

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.
8:00 am to 12:30 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

Middle Street Walk 2025

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.
9:00 am to 5:00 pm

Boot Camp For Birth Support & Beyond

Boot Camp For Birth Support & Beyond for caregivers at Beverly Hospital in Massachusetts
Most education surrounding childbirth focuses on the person carrying the child, as it rightly should. Those in the role of supporting childbirth (spouses, significant others, couples using a surrogate, etc) should be equally as prepared for the joys and challenges in store. In this class you’ll...
9:00 am to 11:00 am

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...
9:30 am to 4:00 pm

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.
10:00 am to 12:00 pm

Christmas at Castle Hill | A Nod to Nature

Christmas at Castle Hill | A Nod to Nature 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 event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
10:00 am to 8:00 pm

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. 
10:00 am to 3:00 pm

CraneExplorer: Coastal Holiday Crafts

Make holiday gifts with beach treasures from the Crane Wildlife Refuge in Ipswich Massachusetts
This holiday season, give a gift from the sea! Beach treasures make beautiful holiday ornaments, jewelry, and keepsakes. Join this workshop to take a beach walk to collect coastal treasures and then make some coastal crafts with our educators. Bring your own shells and beach treasures and we will...
10:00 am to 3:00 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

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...
11:00 am to 1:00 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. Bring the family to Newburyport to visit Santa in his traditional workshop, share your wish list, and snap a photo with Mr. Claus!
11:00 am to 2:00 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

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!
3:00 pm

The Nutcracker Panto - Matinee

Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!
The tree is lit up and the stockings are hung and Clara’s Christmas is perfect…except for her Uncle Drosselmeyer sitting up on that clock and the sudden rat infestation…sounds like panto time!Edward Speck and Joshua Shack return to direct another cracking holiday panto, this time seizing on...
3:00 pm

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...
7:00 pm

Sunday, December 14

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!
1:00 am to 3:00 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

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

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

Christmas at Castle Hill | A Nod to Nature

Christmas at Castle Hill | A Nod to Nature 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 event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
10:00 am to 8:00 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

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. Bring the family to Newburyport to visit Santa in his traditional workshop, share your wish list, and snap a photo with Mr. Claus!
11:00 am to 2:00 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

Sunday STEAM Club at North Shore Children's Museum

Visit Peabody MA, NorthShore, North Shore Children's Museum
Join in on Sundays at 2:30 for STEAM Club for ages 5-11. Each week participants will explore science, technology, engineering, art, and math with our NSCM staff! Every STEAM club session will see your kids participating in hands-on activities while exploring a new topic. Space is limited, please...
2:30 pm to 4:00 pm

The Nutcracker Panto - Matinee

Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!
The tree is lit up and the stockings are hung and Clara’s Christmas is perfect…except for her Uncle Drosselmeyer sitting up on that clock and the sudden rat infestation…sounds like panto time!Edward Speck and Joshua Shack return to direct another cracking holiday panto, this time seizing on...
3:00 pm
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