Subscribe Now

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.

Starting with Small Business Saturday on November 24, be sure to shop local and support your favorite businesses in all four communities with holiday shopping.  Many of the businesses are participating in Small Business Saturday and will have exciting promotions available.

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


The holiday festivities begin in Essex on Thursday, November 29 with the Lighting of the Memory Tree, in Honor of Lost Loved Ones, at Town Hall at 6:30 PM. The following day, Friday, December 1, Santa arrives at Town Landing by boat at 6 PM. Children and families are invited to join for carols, refreshments and the chance to sit on Santa’s lap.


Gloucester kicks off the holiday season on Friday, November 23 with the first ever Downtown Gloucester Holiday Window Contest. The community is invited to visit the businesses and vote for their favorite window display. Look for the “Downtown Gloucester Holiday Window Contest” on Facebook. The voting will be open through December 20. On Sunday, November 25, the Gloucester Christmas Parade begins at the State Fish Pier at 3 PM and marches through the streets of Gloucester, ending at Kent Circle for the Tree Lighting Ceremony at 4 PM. The Annual Ladies’ Night event will take place on Thursday, December 6th.  Enjoy shopping and refreshments in the downtown shops as well as exciting deals and discounts from 5 – 10 PM.  Don’t miss the Middle Street Walk on Saturday, December 8. From 10 AM – 4:30 PM, historic house tours, concerts and special programs will be featured on Middle Street.  Also on the 8th, make sure to stop by the front of the Police Station at 4:30 PM 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.  As we get closer to Christmas, Men’s Night will be held on Thursday, December 20 from 5 – 10 PM.


The events of Christmas by the Sea are also not to be missed.  Visit the downtown merchants for the Manchester Holiday Stroll on Friday, November 30  from 4 – 8 PM.  On Shop Manchester Night, get your passbook stamped at all participating businesses.  Turn it in to 7 Central by 8:00 PM to enter a drawing where the winner will receive an DJI Spark Quadcopter (Drone)! Pick up your passbooks at participating businesses. Spend the day in Manchester on Saturday, December 1, starting with a Pancake Breakfast from 8 -10 AM at 7 Central Restaurant.  In the afternoon, Santa will arrive by boat at 1 PM.  Do the Jingle Bell Walk with Santa to the Manchester Community Center and enjoy festivities until 3 PM.  On Sunday, December 2, join us for a Christmas Concert at 3:30 PM at First Parish Church.  The Lighting of the Friendship Tree will be held at the Town Hall Common at 4:30 PM.


Shop Rockport – Black Friday and Small Business Saturday kick off the Christmas in Rockport holiday festivities on November 23 and 24.  The weekend is dedicated to supporting local small businesses and will include exciting offers from the downtown shops. Friday, November 30 is Rockport’s Annual Holiday Shopping Night.  Shops will be open from 4 -9 PM 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 PM to enter a drawing where two $50 Cape Ann Gift Certificates will be awarded. On the following day, Saturday, December 1, Santa will arrive at T-Wharf by boat at 1 PM and will make his way to Spiran Hall for a Christmas celebration and to visit with children. Festivities will continue in Dock Square with Christmas Carols and the Tree Lighting Ceremony at 4 PM. Christmas Shopping and Art Gallery Stroll Weekend is on December 8 and 9. The shops and galleries of Rockport will be open, each offering different promotions.  New this year is the two-day Rockport Makers’ Festival on December 15 and 16. The festival includes a Holiday Market and Maker-Themed events. On December 15 only there will be an indoor Holiday Farmers Market and free horse drawn carriage rides.  A unique event that engages the entire community, the 73rd Annual Live Nativity Pageant starts at 5 PM on Saturday, December 22. The holiday celebrations are capped off with Rockport New Year’s Eve featuring live music and entertainment from 6 PM to midnight, to ring in the New Year.