Events Calendar - Holiday
Pack the Bus Toy Drive
Pack the Bus Toy Drive at Beauport Hotel
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Deck the Halls: Beauport Hotel Open House
Deck the Halls at Beauport Hotel Gloucester on Dec 2nd (5-8 PM). Enjoy a seaside winter wonderland with live music, festive food, hot chocolate, and ocean views
Jingle Bar: Pop Up Cocktail and Piano Bar
Pop Up Cocktail & Piano Bar
Manchester Division Holiday Party 2025
Manchester Division Holiday Reception- All Manchester Businesses are invited and encouraged to attend! Light appetizers and a Cash Bar will be available.
Annual Holiday Toy Drive
The North Shore & Merrimack Valley Annual Holiday Toy Drive in Rockport!
Holiday Stroll, Manchester-by-the-Sea 2025
The Manchester Holiday Stroll: Downtown Businesses, Manchester. Shop Local. Stroll around town, enjoy refreshments at many shops & collect stamps in your Holiday Stroll Stamp Card.
Rockport Holiday Shopping Night 2025
Christmas in Rockport, Shop, Win, Shop Local
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Home for the Holidays Special
Celebrate the Holidays at Gloucester Stage with Paula Plum and special guests for a one-night only fundraiser.
Squirrel Nut Zippers Christmas Caravan 2025
The Squirrel Nut Zippers bring their joyous, raucous Christmas Caravan Tour back again performing all of the hits from Holidays past.
Backyard Growcery December Pop-Up Market
Gloucester's weekly farmers market The Backyard Growcery is hosting a December Pop-Up Market at The Cut on December 6, 2025
Santa's Arrival for Christmas-by-the-Sea 2025
Santa's arrival in Manchester-by-the-Sea!
Jingle Bar: Pop Up Cocktail and Piano Bar
Pop Up Cocktail & Piano Bar
Luminare Christmas!
Get ready for a holiday rock experience like no other!
Jul Fest at Spiran 2025
The Nordic Christmas celebration, Jul Fest, will be held at Spiran Lodge, Rockport, MA It will include the St. Lucia festival, holiday music, and lunch, Nordic foods including: meats, herring, cheeses will be on sale. Greens and Nordic gifts and linens will also be for sale.
Kids at The Cabot: DJ Willy Wow Holiday Party!
Join us for a family friendly holiday party with DJ Willy Wow!
Ipswich Holiday Stroll & IHS String Quartet Performance
Free Concert - Cider & Holiday Cookies - Free Holiday Gift - Photo booth
Rockport Christmas Carolers 2025
The Solstice Singers will be strolling throughout the downtown and Bearskin Neck, spreading a cheerful and festive vibe all afternoon.
The Milk Carton Kids - Holiday Tour 2025
Folk duo The Milk Carton Kids make a stop on their Holiday Tour 2025!
Christmas with The Celts
New Christmas hits, Celts originals and fresh Irish Dance tunes!
Jingle Bar: Pop Up Cocktail and Piano Bar
Pop Up Cocktail & Piano Bar
A Very Merry Frankie Valli Christmas
A holiday tribute to the music of Frankie Valli & The Four Seasons!
An Enchanted Evening of Winter Solstice: Ritual & Mediumship with Annette Dion
psychic, psychic medium, meditation, salt cave, winter solstice, winter, healing, annette
New Orleans Christmas featuring Henri Smith
New Orleans Singer/Bandleader Henri Smith brings his 7-piece band back to the Gloucester Stage for a special New Orleans Holiday concert.
Cape Ann Makers Market - Last Minute Holiday Gift Market at The Cut!
Last Minute Holiday Gift Market at The Cut hosted by Cape Ann Makers Market. Eat, Drink, Shop Local Makers! Sunday, Dec 21.
MARKETPLACE AT MINGLEWOOD
Discover unique handcrafted treasures from local makers - perfect for those last-minute holiday gifts! SIP - SHOP - CELEBRATE! Hosted by Silver Bear Jewelry
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Zach Nugent’s Grateful Ball
Zach Nugent’s Dead Set isn’t just another tribute; it’s a living, breathing conversation with the music of the Grateful Dead.
Brian Regan
Kick off your New Year's celebrations with comedian Brian Regan!
CAPE ANN BIG BAND NEW YEAR’S CONCERT
CAPE ANN BIG BAND NEW YEAR’S CONCERT
MARTIN LUTHER KING JR. DAY PROGRAM IN THE GLOUCESTER MEETINGHOUSE ON MONDAY, JANUARY 19, 2026
MARTIN LUTHER KING JR. DAY PROGRAM IN THE GLOUCESTER MEETINGHOUSE ON MONDAY, JANUARY 19, 2026
