In December, Boston is at its festive best. With its cobblestone streets and trees strung with twinkling lights, the city takes on a fairy-tale quality that evokes images of both Christmas past and Christmas present.
There is a real timeless appeal to Boston at this time of year. Among Boston’s holiday traditions are ice skating at Frog Pond, strolling Beacon Hill to gaze at the picture-pretty window displays and taking in a performance of the Holiday Pops.
With a nod to my latest book, No Access Boston (Globe Pequot, 2019), here’s a list of Boston’s lesser-known things to do to make magical holiday memories. Who knows? Maybe this Christmas you will find a new tradition!

Outdoor Ice Skating
New Englanders know- there is no better way to embrace winter than to go ice skating.Located in the heart of Boston Common and in the shadow of the State House, the open air skating at Frog Pond is straight out of a Currier & Ives scene.
But there are other, less crowded places to skate outdoors just outside of the city. Two hidden favorites are the Community Ice Skating Rink at Kendall Square in Cambridge and Larz Anderson Park in Brookline.
Boston Ballet’s Nutcracker
Every year, the Boston Ballet brings exquisite dancing to Tchaikovsky’s timeless score against the backdrop of some gorgeous sets to bring the Nutcracker to life. What is less known is that performances of the Nutcracker take place through December 29th and are a wonderful way to extend the season and reclaim the child-like wonder of Christmas.
Boston Holiday Pops
For my family, celebrating the festive spirit of the holidays means attending a Holiday Pops concert at Symphony Hall.
The reading of ‘Twas the Night before Christmas never gets old and I don’t think anyone does “Sleigh Ride” better than the Pops. But the real crowd pleaser is the Pops’ arrangement of the “Twelve Days of Christmas”. It’s a modern mash –up of the traditional carol with Beethoven’s Fifth, My Favorite Things, Bohemian Rhapsody and more. Personally, watching Keith Lockhart do the Can-Can for the Ninth Day is one of the highlights of the entire Christmas season for me!
My Boston Pops Holiday Tip? Like the Boston Ballet, the Boston Pops have shows after the holidays. This year there is a performance of “Bugs Bunny at Symphony” with the Pops playing along to classic Looney Toons like “Kill the Wabbit” projected on the big screen. And every year, the Boston Pops Swing Orchestra does its own “rock-in'” New Year’s Eve concert.
Holiday Afternoon Tea at the Boston Public Library
One of the side effects of wandering Boston at Christmas is cold feet and a craving for sweets. The Boston Public Library offers a wonderful afternoon tea experience year-round in its restaurant overlooking the Italianate Courtyard, but it becomes extra special with a heavy dose of yuletide cheer thanks to glistening holiday décor and a menu that reflects the season. As it turns out, afternoon tea and a library are a delightful combination.
Brattle Book Shop
Passerbys are drawn to the Brattle Book Shop by the shelves and carts heaving with used books in the outdoor lot. That owner Ken Gloss is a local celebrity from his regular appearances as an appraiser on PBS’s Antique Roadshow helps too.
Whether looking for an out-of-print book, a rare first edition or a special literary treasure, during the run-up to Christmas, this well-loved antiquarian shop is a wonderful place to find just the right present.
The Waterworks Museum
During the holiday season Boston-area residents and visitors alike often focus on visiting the city’s big museums; the MFA, the Children’s Museum or the Science Museum (all fabulous, by the way). But you may want to skip the chaos and enjoy a smaller museum from a calmer perspective. Consider the Waterworks Museum. The site was the principal water pumping station for Boston from the late 1800’s until the 1970’s. It’s a quirky little museum that offers a focused view of an unusual collection. In this case three historic, coal powered steam-driven water pumps. As well, the Richardson-inspired Romanesque building is a beauty and the station was also the site of the first laboratory dedicated to biological water analysis. Bonus: Museum admission is free and so too is parking.
Puppet Free Library
For most of us, New Year’s Eve marks the end of the holiday season. New Year’s Eve Boston- style is all about First Night Boston. The city –wide art and cultural extravaganza was founded as a family friendly alternative to New Year’s Eve and inspired countless similar celebrations around the world.
The giant puppets that have become a mainstay of First Night Boston’s parade are made by Sara Peattie, a nationally acclaimed puppeteer and the founder of the Puppet Free Library. Part working studio, part storage vault, and part puppet lending library, the space is located in the basement of Emmanuel Church .This is truly one of the Boston art’s scene’s hidden gems. Do note that the library has extremely limited access and is only open on Tuesdays from 2-5. Sara will lend her puppets to individuals and schools for a day or for a few weeks; for a party, a parade or no reason at all. Just sign your name and leave your phone number. Or simply stop by to visit with Sara and talk with an extraordinary artist and maker.