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Cape Ann Holiday Events

Syndi Zaiger

Syndi Zaiger is the founder of Nest Real Estate...

Syndi Zaiger is the founder of Nest Real Estate...

Jun 11 5 minutes read


So much going on in Cape Ann the next couple of weekends to celebrate the Holiday season. 


Friday Night 12/1


The Manchester Holiday Stroll - MANCHESTER BY THE SEA

FRIDAY DECEMBER 1ST - 4-8pm

Website: https://capeannchamber.com

Event Description:

Formally known as "Shop Manchester Night"

Support Manchester Merchants, shop around town & collect stamps in your Holiday Passbook and you will have a chance to win a new Apple Watch.


Shop Rockport Night & Raffle - ROCKPORT 

FRIDAY DECEMBER 1ST - 4-9pm

Website: https://www.facebook.com/shoprockportma01966/

Event Description:

Downtown Rockport, 4-9 pm. Enjoy a festive Friday shopping evening with many shops and galleries staying open for extended hours and offering exclusive promotions, raffles, and giveaways throughout downtown.


Santa Arrives at Town Landing - ESSEX

FRIDAY DECEMBER 1ST - 6-8PM

Santa arrives on the Essex River by boat and walks up to the shipyard with some of his friends.

   •     Children can sit on Santa’s lap and review their holiday “wish list”

   •     Clam Chowder

   •     Hot Chocolate

   •     Munchkins

   •     Carols by “Sound Waves”

Weather contingency: Friday evening events will be held at Essex Elementary School in case of inclement weather.


SATURDAY 12/2


Annual Annisquam Christmas Fair - GLOUCESTER

SATURDAY DECEMBER 2ND - 8:30 AM - 12:30 PM

Featuring holiday greens, hand-decorated wreaths, center pieces, hostess baskets, gourmet home-baked goods, handicrafts and more. 

Proceeds benefit Cape Ann community programs.


Santa Arrives by Boat - MANCHESTER BY THE SEA

SATURDAY DECEMBER 2ND - 1-3pm

Santa will arrive at Masconomo Park by boat at 1pm. The jolly man will then lead the children across the street to the Manchester Community Center for children's activities and delicious refreshments. Everyone will get a chance to have their pictures taken with Santa!


Santa's Arrival by Boat & Photos with Santa - ROCKPORT

SATURDAY DECEMBER 2ND - 1-3:30pm

Website: https://www.rockportusa.com/event-festival/santas-arrival-in-rockport-and-tree-lighting/

Santa will arrive at Rockport’s T-Wharf on Rockport Harbor on Saturday, December 2, 2017 at 1:00 PM, following a brisk lobster boat ride across Sandy Bay. Then Santa will climb up onto a Rockport Forest Fire truck and proceed along T-Wharf and Mt. Pleasant Street to the Old Firehouse led by Rockport cub scouts. This year Santa will be able to linger a while to visit and have photos taken with the children until the Tree Lighting Ceremony begins (at 4PM). Then Santa will ascend the platform to greet the crowd and kick off the Tree Lighting festivities, before climbing back onto the fire truck to begin his long return journey to the North Pole.


Rockport Tree Lighting

SATURDAY DECEMBER 2ND - 4-5pm

The Tree Lighting Ceremony will get underway at 4 PM welcoming Santa and the public at the Tree in Dock Square with carols and a stirring rendition of “Christmas in Rockport”.

Singers are invited to join the Dock Square Carolers to welcome in the season. A rehearsal for the carolers will be held at the Rockport Baptist Church at 2:30 PM prior to the ceremony.

The Chairperson of the Board of Selectmen will offer official greetings from the Town and then pull the switch to light this year’s Rockport Christmas tree.


Lighting of the Friendship Tree - MANCHESTER

SATURDAY DECEMBER 2ND - 4-5pm

The Official Start of the Holiday Season! After the concert join us in front of the First Parish Church and Town Hall Common. Friendship Tree is sponsored by the Manchester Woman’s Club.


SATURDAY 12/9


Lobster Pot Tree Lighting & Cape Ann Art Haven Open House

SATURDAY DECEMBER 9th - 4:30 - 5 PM

Website: https://ww.capeannchamber.com

Join us on Main Street for the Gloucester Lobster Pot Tree Lighting and Cape Ann Art Haven Open House( immediately following lighting). Come see our newly renovated space, have a hot chocolate & warm up!

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