A 3-Day Itinerary for a Magical Holiday

Christmas is a magical time in Boston. As winter weather sets in, white lights and holiday shows pop up all over New England. Boston’s neighborhoods sparkle every December, with shopping, shows, and plenty of family fun for Christmas. After 400 years of Christmas celebrations in Boston, the city knows how to celebrate the holidays!

Explore our 3-day itinerary for Christmas in Boston, and find the top spots for a holiday experience that the whole family will enjoy. For more holiday fun around Boston, check out our Holiday and Christmas Activities Guide for Boston Kids. And find more New England travel ideas in our Day Trips and Weekend Getaways from Boston Guide.

Christmas in Boston Day 1: North End, Faneuil Hall, and Seaport

North End

The North End is a destination any time of year, and Christmas is no exception. Hanover Street is filled with festive cheer and amazing food. The Trellis Lighting at Christopher Columbus Park kicks off the North End’s holiday season every year. The North End Christmas Parade (typically the second weekend in December) welcomes Santa Claus to town. Be sure to hit the North End for some of Boston’s best dining with kids. Or stop in Cafe Vittoria for one of the best hot chocolate in Boston.

 

The lights at Faneuil Hall sparkle every Christmas in Boston! Faneuil Hall Holiday photo by Daniel Lobo via Flickr 2.0

Faneuil Hall

Shopping at Faneuil Hall is a Boston holiday tradition. Faneuil Hall Marketplace and Quincy market are filled with bright decorations, live music from street performers, and plenty of shops and eateries to keep the family busy for hours. Faneuil Hall is one of the Freedom Trail’s most famous spots, filled withhistory as well as holiday cheer. Boston’s New England Aquarium is right across the street if you’re looking to say “Merry Christmas” to the penguins. And if you time it right, you can catch a cruise with Santa from the nearby waterfront.

Seaport

The “Snowport” turns Boston’s Seaport into a winter wonderland. The Snowport at Seaport features a holiday market with over 100 retailers and artisans. There is curling amnd other winter fun on Seaport Common. Bostons Institute of Contemporary Art sits on the waterfront at the Seaport. The best part of visiting the Seaport at Christmas? All the restaurants bursting with great food and holiday cheer.

 

The holiday shows and performances really take off for Christmas in Boston. Nutcracker photo courtesy of the Boston Ballet 

Christmas in Boston Day 2: Boston Ballet Nutcracker and Boston Common

Boston Ballet Nutcracker

The theater district has plentuy of shows for the holidays in Boston. A 3-day itinerary for Christmas in Boston has to include Boston Ballet’s the Nutcracker. This preeminent performance has drawn visitors to Boston for decades. Other holiday and Christmas shows include How the Grinch Stole Christmas and a Christmas Carol. Swing by Boston’s Chinatown, right down the street, to see one of the most unique Boston neighborhoods decked out for the holidays.

Downtown Crossing

Boston’s Downtown Crossing has a massive Christmas tree at Macy’s. It might not be on 34th Street, but this Macy’s has the feel of a traditional department store. You might even bump into Kris Kringle. One of our favorite Christmas events, the all-tuba Christmas Concert, takes place in Downtown Crossing every year.

Boston Common

Every Year, Boston Common and the Public Garden are lit up for the holidays. The 2024 Boston Common Tree Lighting takes place on December 5, and the massive tree will be on display throughout the month. Keep your eyes peeled for live performances, and strap on skates for outdoor ice skating on Frog Pond. 

South End

Nestled amid the brownstones, Boston’s South End has a bistro for the most discriminating pallette. Right on Huntington Street and Massachusetts Avenue, Symphony Hall hosts some fabulous family-friendly Christmas shows and performances by the Boston Pops. The BSO’s Holiday Pops Concert will be playing almost every day in December. And the SoWa Winter Festival is one of our favorite winter fests in Boston, with shopping, food, and holiday fun.

 

See Muppet Christmas Carol at the Coolidge Corner Theatre in Brookline. Muppet Christmas Carol, copyright Buena Vista Pictures

Christmas in Boston Day 3: Harvard Square and Back Bay

Harvard Square

There are so many things to do with kids in Harvard Square, and the holidays are no exception. From holiday markets to shopping to live music on the streets, Harvard Square is a magical Christmas neighborhood. Check out the tree in the upper courtyard of the Charles Hotel. In addition to the shops that call Harvard Square home all year long, there are multiple holiday fairs where you can find arts, crafts, and unique gifts. And the Midwinter Revels on the Sanders Theatre stage are a fun local tradition for the holidays.

Back Bay

Boston’s Back Bay has so much to offer at Christmas, especially for shoppers! The Prudential Mall and Copley Place have plenty of indoor stores, as well as Christmas carolling and visits with Santa! Boylston and Newbury Streets are bustling with shoppers exploring the one-of-a-kind stores and galleries. Copley Square often hosts seasonal events and fairs.

MFA and Isabella Stewart Gardner Museum

Boston’s Fenway neighborhood is known for the world-famous baseball park, but it’s also home to world-class museums. The Museum of Fine Arts and the Isabella Stewart Gardner Museum have Christmas and Hanukkah events to celebrate the season.

Coolidge Corner

Head to Brookline’s Coolidge Corner for Christmas fun, including the Muppert Christmas Carol at the Coolidge Corner Theatre. Brookline Booksmith is a wonderful stop on a holiday shopping trip around Boston; it’s one of New England’s most beloved independent bookstores.

 

Take in Christmas by Candlelight on a holiday trip to Boston at Christmas. Photo courtesy of Old Sturbridge Village

Christmas in Boston: Day Trips from Boston for Holiday Magic

Looking to extend a holiday trip to Boston? Try these side trips for New England holiday magic.

Christmas by Candlelight at Old Sturbridge Village

See what an old New England Christmas would look like with a trip to Old Sturbridge Village, a living museum in Sturbridge, Massachusetts. Christmas by Candlelight Sturbridge runs throughout December.

Strawbery Banke – Portsmouth, NH

There are plenty of things to do in Portsmouth, NH, and seeing the festive decorations of Strawbery Banke on a candlelight stroll at Christmas time is definitely worth the drive!

Holiday Lights Spectacular – Providence, RI

The Holiday Lights Spectacular at Roger Williams Park Zoo is a wonderful family activity that draws visitors to Providence every Christmas.