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.
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 2024.
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 be available for download on December 1, 2024 at this link.
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 during the Middle Street walk with winners being announced at 1pm in Gloucester City Hall.
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! Social dogs very, very welcome!
Come to Cruiseport Gloucester to the Cape Ann Makers Holiday Market. Support your local economy and makers by shopping local. Saturday, November 24, 2023, is Small Business Saturday. When shopping local please come by to Cruiseport Gloucester for the Holiday Sip and Shop Market.
Step back in time at our Renaissance Faire Day! Immerse yourself in the enchanting world of medieval and Renaissance culture with live performances by The Harper & The Minstrel and the L.I.A.R.S. (Ladies of Integrity, Aristocracy, Repute, and Society), offering a mesmerizing blend of medieval, Renaissance, and Celtic music as they stroll through the Museum and grounds.
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.
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.
Come party with Cape Ann YMCA for Halloween! FREE FAMILY EVENT! Join the fun and decorate your trunk, wear a costume, and hand out candy or prizes! Please keep all themes family friendly.
