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This time of year is filled with community traditions and holiday events in Essex, Gloucester, Manchester-by-the-Sea and Rockport. With a wide array of wonderful celebrations, visiting Cape Ann is a must this holiday season. 

All of Cape Ann will be bustling during the month of December. Each of the four communities have many events that local residents and visitors are invited to enjoy. 


The holiday festivities begin in Essex on Thursday, December 5 with the Lighting of the Memory Tree, in Honor of Lost Loved Ones, at Town Hall at 6:30 p.m. The following day, Friday, December 6, Santa arrives at Town Landing by boat at 6 p.m. Children and families are invited to join for carols, refreshments, and the chance to sit on Santa’s lap. 


Gloucester kicked off the holiday season on Sunday, November 30 with the Gloucester Christmas Parade and Kent Circle Tree Lighting Ceremony. “Deck the Docks” returns to Maritime Gloucester with special holiday programming December 4 through the 8. The Annual Ladies’ Night event will take place on Thursday, December 5. Enjoy shopping and refreshments in the downtown shops as well as exciting deals and discounts from 5 to 10 p.m.

Don’t miss the Middle Street Walk on Saturday, December 14. From 10 a.m. to 4:30 p.m., historic house tours, concerts, and special programs will be featured on Middle Street. Also on the 14th, make sure to stop by the front of the Police Station at 4:30 p.m. for a truly unique Gloucester tradition, the lighting of the Lobster Trap Tree, decorated by the children of Cape Ann Art Haven, and stop in to Art Haven after the lighting for an open house.

The Gloucester Holiday Window Contest is open for voting through December 19—visit the shops and vote for your favorite window display on Facebook. As we get closer to Christmas, Men’s Night will be held on Thursday, December 19 from 5 to 10 p.m.


The events of Christmas by the Sea are also not to be missed. Visit the downtown merchants for the Manchester Holiday Stroll on Friday, December 6 from 4 to 8 p.m. On Shop Manchester Night, get your passbook stamped at all participating businesses. Turn it in to Antique Table by 8 p.m. to enter a drawing where the winner will receive an Apple Watch! Pick up your passbooks at participating businesses.

Spend the day in Manchester on Saturday, December 7, starting with a Pancake Breakfast from 8 to 10 a.m. at Antique Table. In the afternoon, Santa will arrive by boat at 1 p.m. Do the Jingle Bell Walk with Santa to the Manchester Community Center and enjoy festivities until 3 p.m. On Sunday, December 8, head to the Christmas Concert at 3:30 p.m. at First Parish Church. The Lighting of the Friendship Tree will be held at the Town Hall Common at 4:30 p.m. 


Friday, December 6 is Rockport’s Annual Holiday Shopping Night. Shops will be open from 4 to 8 p.m. (or later) for the occasion and will offer special deals and refreshments for shoppers. Participating businesses will be giving out raffle tickets to be turned in at the Fish Shack Restaurant by 8:30 p.m. to enter a drawing where two $50 Cape Ann Gift Certificates will be awarded. On the following day, Saturday, December 7, Santa will arrive at T-Wharf by boat at 1 p.m. and will make his way to Rockport’s Baptist Church to visit with children. Festivities will continue in Dock Square with Christmas Carols and the Tree Lighting Ceremony at 4 p.m.

The two-day Rockport Makers’ Festival returns for a second year on December 14 and 15. The festival includes holiday markets and maker-themed events, artist demonstrations at local galleries, strolling musicians, a craft beer and spirits tent, and free horse-drawn carriage rides.

A unique event that engages the entire community, the 74th Annual Live Nativity Pageant unfolds on Saturday, December 21. The holiday celebrations are capped off with Rockport New Year’s Eve featuring live music and entertainment from 6 p.m. to midnight, to ring in the New Year. 

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