Discover the Magic of the Holidays North of Boston

Discover the Magic of the Holidays North of Boston

November 28, 2022

Thanksgiving may be over but North of Boston we give thanks all year long. Throughout the holidays we especially can’t imagine spending these magical few weeks anywhere more charming than right here.

Our area is already packed with classic New England seaside charm, adorn it with holiday decorations and heartwarming merriment and you can’t get a more idyllic setting. From tree lightings to holiday markets, concerts, parades, and ample opportunities to hobnob with Santa himself, it’s an exciting month for visitors and residents alike. We hope you’ll join us for some of the festive fun happening this holiday North of Boston.

Don’t Miss These Popular Events Happening All December Long

Through December 30: Deck the Halls at Hammond Castle
The beautiful and historic Hammond Castle transforms for the season! Visit for a guided tour of this iconic Gloucester landmark on Fridays, Saturdays, and Sundays through the end of the year. For an extra special treat attend a Deck The Halls by Candlelight event, happening every Thursday in December.

Weekends in December: Christmas at Castle Hill
Don’t miss this year’s fantastical An Enchanted Christmas. Each room in the Crane Estate’s 1920s mansion is decorated for the holidays drawing inspiration from favorite stories. Christmas at Castle Hill runs Fridays, Dec. 2, 9, 16; Saturdays, Dec 3, 10, 17; Sundays, Dec. 4, 11, 18; and Dec. 27-31.

Through January 1: Winter Lights on Cape Ann
Celebrate the spirit of the season on Cape Ann! Pack up the car and enjoy the 3rd Annual Winter Lights on Cape Ann. Local businesses throughout Gloucester, Essex, Ipswich, Manchester-by-the-Sea, and Rockport are getting into the festive spirit by decorating their storefronts with twinkling lights and creative window displays!

Weekends in December: Holidays on the Hill
Join The Trustees at Long Hill in Beverly for Holidays on the Hill the first three weekends in December. Get in the holiday spirit by marveling at the decorations in the main house, playing a reindeer scavenger hunt in the gardens, gathering around the fire pits on the terrace, making ornaments on the porch, and more!

Mark Your Calendars for these Festive Family Friendly Events!

Dec. 1–4: Deck The Halls with Maritime Gloucester
This year marks the 5th annual Deck the Docks brought to you by Discover Gloucester, and spans four days of festive fun! Sip on cider and cocoa, participate in sing-alongs and crafts, snap photos with Santa, witness the Lighting of the Pier, shop Christmas trees, wreaths, and goodies from local vendors, and much more family fun!

Dec. 1–4: Marblehead Christmas Walk
Join the Marblehead Chamber of Commerce December 1st – 4th for a festive weekend including the tree lighting, Santa’s arrival by lobster boat, a parade, artisan markets, the Gingerbread festival, music, and so much more!

Dec, 1–4: Christmas-by-the-Sea
The Greater Cape Ann Chamber of Commerce brings you a Holiday stroll, Santa (who arrives by boat!), a parade, caroling around town, warm hot cocoa, and tons of family activities for your enjoyment in Manchester-By-The-Sea.

Dec. 2: Lighting of the Custom House Maritime Tree & Sing-A-Long
The Maritime Tree reflects Newburyport’s community spirit with replica life rings used as ornaments, tied together to reflect our commitment to each other during the Holidays. Join in the Tree lighting and sing-a-long on Friday, Dec. 2, and help the Custom House light up the Newburyport waterfront by purchasing a life ring.

Dec. 3: Amesbury Holiday Parade
The town of Amesbury is proud to bring you the 58th annual Holiday Parade! The theme this year will be community. Come out and bring the family for a holly jolly good time.

Dec. 3: Cape Ann Artisans Holiday “Pop In” Show and Sale
Cape Ann Artisans welcome the public into their studios for a holiday show and sale. Enjoy visiting artists in their studios across Cape Ann at this festive time of the year. Fifteen locations result in a variety of media for holiday shopping in the neighborhood. Plan your perfect self-guided tour with the help of the event brochure and map.

Dec. 3: Saint Bernards at Smolak Farms
On Saturday, December 3rd from 10 am – 3 pm, Smolak Farms is welcoming Saint Bernards back to the farm! Families can come out and choose from their extensive selection of pre-cut trees and the lovable and gentle Saint Bernards will be around to pull the back to your car. Don’t miss this exciting holiday photo opp and the chance at an unforgettable winter day!

Dec. 3: Christmas in Rockport
Christmas in Rockport is a season long celebration! On Saturday, December 3rd from 12:30 to 5:00 pm delight in the cherished Rockport tradition of Santa’s arrival by lobster boat, the Dock Square Tree Lighting ceremony and more!

Dec. 11: Santa at Sea with Beauport Cruiselines
Enjoy a holiday harbor cruise on Beauport Cruiselines on Sunday, December 11th. Set sail for an afternoon of holiday cheer, with sailings at 11 am and 2 pm. Enjoy a reading of “Twas the Night Before Christmas” while sippin’ hot cocoa and munchin’ on cookies. Plus a visit from Santa himself!

Dec. 10: Middle Street Walk, Gloucester
Stroll on Gloucester’s historic Middle Street filled with free events featuring music, kids’ activities, tours of historic houses and museum exhibits, and more!

Dec. 10: Lobster Trap Tree Lighting, Gloucester
Gather together on Main Street for Gloucester’s Lobster Trap Tree Lighting for this family-fun activity! Lobster Traps and Lobster Buoys, decorated by the children of Cape Ann Art Haven, make up this distinctly unique Christmas Tree in downtown Gloucester.

Dec. 17: Lunch with Santa at Davio’s Lynnfield
Dine with Kris Kringle himself! On Saturday, December 17th from 10 am to 2 pm Davio’s welcomes families for a two-course Prix Fixe menu plus pictures with Santa! Guests can choose from one of five seatings.

Dec. 17: Santa in Salem at the Phillips House
Santa and Mrs. Claus are coming to Phillips House in Salem! Take a photo with Santa and see the elegant Chestnut Street mansion aglow with holiday cheer. Plus stories with Mrs. Claus, cookies, cider, Christmas craft workshop, and letter writing to Santa!

Photo credits: Holidays on the Hill courtesy The Trustees – Long Hill, Deck The Halls courtesy Hammond Castle Museum, Christmas at Castle Hill courtesy The Trustees – Crane Estate, Custom House Maritime Tree courtesy Custom House Maritime Museum, Lobster Tree Lighting courtesy Discover Gloucester.