Gloucester

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 2025.

When: 
Saturday, December 14, 2024 10am-7pm

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 Community Safety Day 2024

Come to Harbor Loop for a kid friendly day of public safety demonstrations by the US Coast GaurdGloucester Fire Department and Police.

United States Coast Guard Station Gloucester is having an open house and safe boating day! Stop by and learn all about the Coast Guard and its important role in Gloucester. The United States Coast Guard Station Gloucester annual Safe Boating Day Open House will feature local marine vendors, safe boating displays, flare demonstrations, tours of Coast Guard vessels, and more. Free to the public. Recreational boaters, commercial boaters, loads of fun for the kids!

When: 
Saturday, September 28, 2024 10am-2pm

It’s a Hard Dock Life at Maritime Gloucester

Finding and Identifying Marine Invasive Species at Maritime Gloucester in Massachusetts as partof Trails& Sails

Maritime Gloucester invites participants to pull up dock lines on the pier and see what marine creatures we can find! Using magnifying glasses, microscopes, and identification cards, we’ll discover as many marine invasive critters as we can. After investigating the dock, we encourage families to explore the Maritime Gloucester Campus, including the Seapocket Aquarium, the Marine Science & Education Center, and Gorton’s Seafood Gallery of Maritime Heritage in Gloucester, all free of charge.

When: 
Saturday, September 15, 2024 10am-3pm

Falconry & The Medieval World | Hammond Castle

Bring your kids to the Hammond Castle Museum in Gloucester Massachusetts for a live falconry presentation

Falconry is the sport of hunting with a trained bird of prey. It is also the demanding art of training a predatory bird that is by nature wary of people to hunt cooperatively with a human partner. Although the sport has a 4,000 – year history, its glory days were indisputably the medieval period.  While this presentation centers around live birds used in falconry, it is not a flight demonstration but a history-rich look at an ancient sport. Focusing on the medieval period, it explains the characteristics of the birds of prey used, how the sport reflected the lifestyle of the time, and the historical reasons behind falconry’s rise and fall.

When: 
Sunday, August 20, 2023 10am-2:00pm

Ocean Views Walk from Ravenswood to Rafe's Chasm

Take a hike along the newly created trail links the southern edge of the Trustees of Reservation's Ravenswood Park with the City of Gloucester's Rafe's Chasm Park.

Join us for a hike across Magnolia Woods to the oceanside cliffs of Rafe’s Chasm! This 3-mile round trip hike takes us through a 300-acre area of woodlands owned by the City of Gloucester (across the street from Ravenswood Park), out to Rafe’s Chasm, which features spectacular views of the ocean from rocky cliffs.

When: 
Saturday, September 21, 2024 10am-12:30pm
Location: 

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Appleton Farms offers great farm-based Vacation Week Programs for kids ages 5-11

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

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

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 e
10:00 am to 4:00 pm

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

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

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

Cape Ann Symphony Holiday Pops

Cape Ann Symphony Holiday Pops Concert in Ipswich and Manchester Massachsusetts
Celebrate the Holidays on Thanksgiving weekend with the Cape Ann Symphony conducted by Yoichi Udagawa. The annual Holiday Pops is a musical celebration of the season.
2:00 pm

Friday, December 5

Tree Lighting in Marblehead

Marblehead's tree lighting is always a festive occasion to kick off the holidays
The Tree Lighting will take place at the new National Grand Bank Parking Lot on Pleasant Street in Downtown Marblehead this year!  Enjoy the festive atmosphere and live music as the town lights the yearly Christmas tree! Festivities begin at 5:30pm with the tree lighting at 7pm.
5:30 pm to 7:00 pm

SeaFestival of Trees | Blades Night

Celebrate with holiday with the Bruins Mascot at the SeaFestival of Trees in Salisbury Massachusetts
Come tho the SeaFestival of Tree for a special Bruins themed night! Wear your Bruins apparel, meet the Bruins mascot and skate on the Seaaside Ice indoor rink! Enjoy a scavenger hunt through a maze of sparkling trees, visit Santa, and enjoy the candy cane forest. Skate rentals available. 
6:00 pm to 8:00 pm

Hamilton-Wenham Carol Sing & Tree Lighting

Hamilton-Wenham Community hosts a community carol sing and tree lighting in Massachusetts
The Community House Of Hamilton & Wenham invites children to join us for a jolly evening of carol singing and holiday cheer, led by Kimberly Robertson, Music Director for Stage 284! Santa will be arriving in style at about 7:15pm. Free to attend!
6:30 pm

Saturday, December 6

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

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,...
9:00 am to 9:00 pm

Santa Arrives in Marblehead

Come to Marblehead to welcome Santa as he arrives for the Christmas Walk!
Come to the State Street Landing in Downtown Marblehead to welcome Santa as he arrives by lobster boat!  There's plenty of photo ops and Santa's arrival is followed by the Marblehead Christmas Walk Parade. 
9:00 am

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

2025 Marblehead Gingerbread Festival

The Marblehead Gingerbread Festival is part of the Marblehead Chamber of Commerce's Christmas Walk, and the proceeds will go to benefit the Marblehead Family Fund and the Marblehead Historical Society.
Come see over 100 locally and professionally made gingerbread creations on display at the historic Jeremiah Lee Mansion in Marblehead, MA during this year's Marblehead Christmas Walk. Community members, businesses, and families are building and donating dozens of gingerbread houses, boats and local...
10:00 am to 4:00 pm
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