Middle Street Walk

Gloucester's So Salty 2026

Celebrate Gloucester Massachusetts recognizably salty character with local cultural institutions in the heart of downtown.

Celebrate the fish city’s recognizably salty character with local cultural institutions and businesses during the 5th Annual Gloucester’s So Salty festival sponsored by the Cape Ann Museum in partnership with Discover Gloucester! This annual event brings over 2,000 people to the downtown area each January to shop at local stores, enjoy family friendly activities, visit the Museum Courtyard, and find each of the ice sculptures sponsored by local cultural institutions and businesses.

When: 
Saturday, January 24, 2026 10am-4pm
Sunday, January 25, 2026 10am-4pm
Location: 
Downtown Gloucester
Cape Ann Museum
Gloucester Unitarian Universalist Church
Sawyer Free Library Temporary Space
Local Colors
Gloucester
Holiday
Walk
Food
Performance
Museum
Dance
Live Performance
Exhibit
Library
Crafts
Art
Tree Lighting
Middle Street Walk

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

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

Holiday at Hogsmeade

Enjoy a Harry Potter themed Holiday celebration at the Sawyer Free Library in Gloucester!

Sawyer Free Library invites kids and families to celebrate the Holidays at a Harry Potter themed party during the Middle Street Walk in Gloucester! Come for a jolly journey around the Wizarding World! It will be a Happy Holiday at Hogsmeade as we sample butterbeer, as well as many more activities such as wand-making, the sorting hat, a photo booth, family trivia, crafts, and more!

When: 
Saturday, December 14, 2019 11am-2pm
Location: 
Sawyer Free Library
Gloucester
Crafts
Food
Harry Potter
Middle Street Walk
Reading
Library
Party

Wingmasters at Sawyer Free Library

Wingmasters demonstrate live birds of prey of various specious in Massachusetts

Join the specialists of Wingmasters for a live birds of prey demonstration at Sawyer Free library during the Middle Street Walk in Gloucester!  Birds of prey are also known as raptors, and they are hunting birds characterized by hooked beaks and powerful grabbing feet armed with sharp talons (the word raptor comes from a Latin word that means "to seize"). Raptors can also boast the best eyesight and the sharpest hearing in the animal kingdom. Raptors include hawks, falcons and owls. This program is for ages 6 & up. This live presentation introduces 5 live birds of prey, all native to New England! All audience members must be seated in chairs, maximum capacity is 70 people.  For more info, contact Christy Rosso.

When: 
Saturday, December 14, 2019 11am-Noon
Location: 
Sawyer Free Library
Gloucester
Education
Demonstration
Live Animals
Presentation
Library
Middle Street Walk

Lobster Trap Tree Lighting

Lobster Trap Tree Lighting Party in at Cape Ann Art Haven in Gloucester Massachusetts

The annual Middle Street Walk in Gloucester wraps up every year with the lighting of the lobster trap Christmas tree in Gloucester Massachusetts! Stop by Cape Ann Art Haven for a Holiday Party with hot chocolate, sweet treats, kids' crafts, holiday photos, face painting live music. Caroling starts at 4:30pm, followed by the tree lighting across the street at 5pm. Come find your buoy hanging on the tree, enjoy caroling, seeing the star put on the tree join us for the countdown and celebrate the season with the lighting of our Lobster Trap Tree!

When: 
Saturday, December 14, 2019 4-6pm
Location: 
Downtown Gloucester
Cape Ann Art Haven
Gloucester
Holiday
Walk
Food
Performance
Museum
Dance
Santa
Live Performance
Exhibit
Library
Crafts
Art
Tree Lighting
Middle Street Walk
Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich 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!
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
♦ Read More →

LEGO Club at Danvers Library
LEGO club at Danvers Library Massachusetts
Peabody Institute Library - Danvers invites kids to an afternoon of building and fun! Activities will include free build, themes and instructional design. All structures will remain on display in the Children’s Room till the following weeks's session
Where: Peabody Institute Library - Danvers
3:30 pm to 4:30 pm
♦ Read More →

Friday, March 13

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 →

Saturday, March 14

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 →

Maple Sugaring at Breakheart Reservation
Come to Breakheart Reservation Saugus Massachusetts to learn about maple sugaring - the process of making syrup..
Come to Breakheart Reservation for this FUN annual event! Experience the process of maple sugarin’ from tapping a tree to sampling real maple syrup.
Where: Breakheart Reservation
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
♦ 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
♦ Read More →

2nd Saturday at Lynn Museum
Lynn Museum in Massachusetts offers free admission on the second Saturday of each month.
Come to the Lynn Museum and Historical Society for FREE family fun. Join us on the second and fourth Saturday of each month for FREE admission to the Museum from 10 a.m. – 2 p.m.! You can view our latest exhibitions, purchase Lynn-themed goods in our shop, check out books in our free library, and...
Where: Lynn Museum and Historical Society
10:00 am to 2:00 pm
♦ Read More →

Maple Sugaring Saturday at IRWS
Sugaring Off tours are a fun and tasty way to learn about maple sugaring at IRWS
Experience the age-old tradition of maple sugaring at Ipswich River Wildlife Sanctuary! The warm days of late winter awaken the flow of sap in the maples resulting in sweet-smelling, billowing clouds of steam rising from the sugarhouse. On a naturalist-guided walk, learn how to identify a sugar...
Where: Ipswich River Wildlife Sanctuary
10:30 am to 3:30 pm
♦ Read More →

Sunday, March 15

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 →
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