Christmas In Rockport, MA – The Full Event Calendar
Here at the Addison Choate we are looking forward to Christmas in Rockport, MA.
It’s a time that we’re reminded to shun our proclivities to become squeezing, wrenching, grasping, scraping, clutching covetous old sinners, and focus on generosity, kindness and charity.
If you’re looking to rekindle a little of that holiday magic, you should consider a weekend trip to Rockport, Massachusetts. It’s is bustling all December long and the charming village conjures up memories of Christmas past.
Every weekend in December, Rockport offers events and gatherings to celebrate the holiday. From tree lightings, to Santa’s arrival by boat and local artists and artisans demonstrating their crafts, it’s a refreshing month-long celebration. Here is the full Event Calendar:
Looking for the perfect holiday gift without breaking the bank? Don’t miss Rockport Holiday Shopping Night, where local shops stay open late and offer exclusive discounts, prizes, and seasonal cheer. Stroll through downtown Rockport to discover unique, thoughtful gifts from small businesses—all while soaking up the festive atmosphere.
Start by picking up a free festive tote bag in Dock Square, then shop participating retailers to earn raffle tickets. Cap off the fun at Brackett’s Oceanview Restaurant, where raffle winners are announced and gift cards from local businesses are up for grabs!
Don’t miss the Cape Ann Big Band as they return to the spectacular Shalin Liu Performance Center in Rockport, MA for a festive holiday showcase! This spirited ensemble of talented local musicians is known for energizing performances that blend jazz, swing, soul, and rock ’n’ roll into a joyful seasonal soundtrack. Whether you’re a longtime fan or discovering them for the first time, their lively arrangements are guaranteed to get your holiday spirits soaring.
You’ll have three chances to catch the Cape Ann Big Band on December 5th and 6th—a highlight of Christmas in Rockport and one of the region’s most beloved holiday concerts.
On December 6th at 1:00pm you can catch up with the big man himself and make one last plea for the “nice” list. Santa will arrive in Rockport in style aboard a lobster boat, of course. How else would Saint Nick arrive in Rockport?
Santa will take a brisk ride across Sandy Bay before docking at T-Wharf and greeting the cheerful crowd. After that, Santa will hop aboard a forest fire truck and head to his Rockport workshop at the Baptist Church from 1:15pm to 1:30pm where he will visit and have photos taken with children and maybe some older children too…
Then Santa will meander over to Dock square and greet the crowd for the Tree lighting festivities. After which Santa hops on a fire truck to escort his jolliness back to the North Pole to put on the final touches for Christmas.
After you’ve had a chance to get a photo with Santa and maybe warm up with a nice cup of chowder or in front of the fireplace at the Addison Choate, you can head over to Dock Square for the annual tree lighting.
The scene at Dock Square is out of a Hallmark movie and has been beautifully chronicled in Jean Woodbury’s book, The Tree in Dock Square. There is also a fantastic video called The Tree By The Sea, documenting the process of finding a local tree, cutting it down and bringing it Dock Square.
Looking for one of the most magical Christmas in Rockport experiences? Few things feel more romantic during the holidays than a horse-drawn carriage ride—especially along Bearskin Neck, Rockport’s charming seaside village. This beloved Rockport MA holiday tradition is back again this year, thanks to Dan Tuck and Tuck’s Candy, longtime supporters of the community.
During your visit, explore the boutiques and galleries along Bearskin Neck, soak up sparkling coastal views, and enjoy the nostalgic treat of a carriage ride through historic downtown Rockport. You will also be serenaded by the holiday sounds of strolling carolers between 1pm and 3pm. It’s one of the top things to do in Rockport in December and a must-add to your Cape Ann holiday itinerary.
Experience another unforgettable holiday performance at the Shalin Liu Performance Center in Rockport, MA as acclaimed vocalist and pianist Tony DeSare takes the stage. Known for his fresh, contemporary approach to the Great American Songbook, DeSare blends jazz, swing, and pop with effortless charm and dazzling virtuosity.
From timeless favorites inspired by Frank Sinatra and Billy Joel to his own award-winning original compositions, DeSare delivers a program filled with rich storytelling, soaring melodies, and seasonal spirit. His engaging stage presence and dynamic arrangements make for an evening that feels both nostalgic and refreshingly new.
Celebrate Christmas in Rockport with a concert of beloved holiday classics and crowd-pleasing gems performed by one of today’s most captivating artists—an event not to be missed at Shalin Liu.
On Saturday, December 20th you can also watch a torch-lit live re-enactment of the Nativity on Dock Square and Main Street by the Rockport Art Association.
The event was originally created by Dr. William F. Strangman Mrs. Aldro Hibbard as a gift from the Rockport Arts Association to the village. It’s still organized by the Rockport Art Association and Museum and each year hundreds of spectators gather to witness this impressive live event. Witness the story of baby Jesus in the Bethlehem Inn and stable.
The pageant kicks off with a torch lit procession through Dock Square and up Main Street to the Congregational Church where the timeless story is brought to life.
Ring in the New Year with Rockport New Year’s Eve! With 60 shows across 14 different venues, New Year’s Eve in Rockport is fun-filled way to book end the year that has passed and acknowledge the exciting new adventure to come.
There is free parking at Whistlestop Mall and a bus service from the parking lot and train station. If you’re staying at Addison Choate, our Rockport, MA Hotel, we have parking for each of our rooms on-site and you can just walk downtown to the festivities.
The events kick off around 6pm and run until the ball drops. Performances include a wide-variety of music, story-telling, puppets and much more! Buttons, purchased in advance, are only $15 for adults and $10 for kids and children 12 and under are admitted free of charge. Buttons purchased from December 25th on are $20 for adults and $10 for kids. You can purchase your Rockport New Years Eve buttons here.
So you’re feeling a bit like scrooge, take a weekend to visit us here on the North Shore. We would love to have you stay in one of our rooms at the Addison Choate. Christmas in Rockport is sure to turn any Scrooge back into a Fred.
We will leave you with this quote from Fred: “I have always thought of Christmas-time, when it has come round-apart from the veneration due to its sacred name and origin, if anything belonging to it can be apart from that-as a good time; a kind, forgiving, charitable, pleasant time; the only time I know of, in the long calendar of the year, when men and women seem by one consent to open their shut-up hearts freely, and to think of people below them as if they really were fellow-passengers to the grave, and not another race of creatures bound on other journeys.”
