9 Best Things to Do in Boston in Winter

Experience the winter magic of outdoor ice skating on Boston Common’s Frog Pond. Bask in the beauty of nature, just a stone’s throw from the bustle of the city, as you glide gracefully around the rink. Beginners are welcome, and children can borrow cute seal-shaped skating aids to help them gain confidence on the ice. Lessons are also available for all ages. There’s a cafe serving hot cocoa and tasty Belgian waffles if you’d like to warm up before or after your icy adventure.

You’ll find the Frog Pond a short walk from city centre Boston, or take the T to Park Street. Arrive after sunset to experience the twinkling lights of Boston Common as you zoom across the ice.

Visit one of Boston’s fabulous European-style seasonal markets to find exquisite food, warming drinks, and tasty treats of all types. Artisans sell handmade craft items and unique products, and you can browse for special gifts among the wide range on offer. Many of the markets also have programmes of activities for all ages, as well as street entertainers and live music.

You’ll find holiday markets near the stores at City centre Crossing, in Harvard Square, and in Boston’s South End, among other locations. Or try taking a bus tour of the city, and ask your guide to point out the best places to stop for your seasonal shopping exploration.

The TD Garden is the largest sports and entertainment arena in New England, and home to the NHL’s Boston Bruins and the NBA’s Boston Celtics, as well as holding large concerts, wrestling matches, and family shows. You’ll find the TD Garden easily by travelling to North Station.

During the winter months, you can buy tickets for Celtics and Bruins games at the TD Garden Box Office on the North Station concourse, or through an online vendor. Whether you enjoy basketball or hockey, or both, you can be sure of an exciting time watching the sporting action unfold. The venue’s great sound and lighting provide a fantastic atmosphere, the seating is comfortable, and there are a variety of food and drink options in and around the stadium.

Leave the bustle of the city behind and head for the snow-topped hills. The Blue Hills Reservation is a large state park in Norfolk County, Massachusetts, about 16 miles south of Boston, and easily accessible on the I-95 and I-93.

There are 22 hills in the Blue Hills chain, each with trails that offer amazing forest hikes and scenic views. Relish the tranquility of snowshoeing through the sparkling white landscape. You’ll find trails for all levels of snowshoe expertise, from complete beginner to seasoned pro. Get hold of a Blue Hills trail map to find a route that’s perfect for you. Then take to the hills and explore the spectacular snowy scenery.

Join the Mayor’s Enchanted Trolley on a fabulous tour that brings holiday spirit to the whole of Boston. The event takes place in various areas throughout the city. It’s an annual tradition that includes festive entertainment, tree lighting, and other seasonal activities.

At each event, enthusiastic crowds gather to enjoy holiday music, delicious food, and a chance to meet with Santa Claus and Mrs. Claus. The Enchanted Trolley tour’s fun events, organised by the Mayor's Office of Tourism, Sports, and Entertainment, are free to all Boston residents and visitors.

Hop aboard a holiday cruise from Boston Harbour and add a magical marine touch to your winter fun. You’ll glide gently along the ocean with a backdrop of Boston’s skyline and glimmering lights.

Take in the glorious views of the city, with highlights including the Boston Harbour Islands, USS Constitution, and the Bunker Hill Monument. Join a holiday celebration with live music and complimentary warming drinks aboard a 1920s-style yacht. Or try an Irish cruise with carol-singing and cosy cocoa drinks.

Grab a plastic sleigh or wooden toboggan and make your way to Boston’s high ground to join in the sledding fun. The city’s many public parks give plenty of options for the perfect sledding experience, and you could even try a sledding tour of several snowy locations.

One of the most popular places for sledding is Flagstaff Hill on Boston Common, but you could also try Danehy Park in Cambridge, Prospect Hill Park in Waltham, Thomas Park in Dorchester Heights, Larz Anderson Park in Brookline, Arnold Arboretum in Jamaica Plain, and many more. Wherever you choose, hold on tight and enjoy the ride as you cascade down snow-covered hillsides with the wind in your hair.

Located in the South End of Boston, the SoWa district is a centre of style and energy, full of artist studios, galleries, and boutiques. When winter comes around, the SoWa Winter Festival brings festive cheer to the fashionable streets.

A visit to the SoWa Winter Festival will give you the chance to shop at more than 100 stands that showcase some of the neighborhood’s most fascinating artists, designers, and speciality food vendors. Browse through original crafts, vintage clothing, and homemade products to find the perfect gifts for the holiday season. Then relax in the warmth of one of the tents and enjoy some refreshments as you soak up the festive atmosphere.

There’s nothing cosier than settling by the fire and shutting out the blustery cold, and that’s exactly what you can do at the trendy River Bar in Somerville. Snuggle by a fire pit on the covered patio, and enjoy scenic views of the Mystic River as you sip a special warming cocktail. You can choose from Irish coffee, spiced wine, and cocoa drinks that feature Belgian hot chocolate with a touch of liqueur. If you’re in the mood for a tasty snack, try the crispy calamari, loaded nachos, or snowbird chicken platter.

You’ll find the River Bar in the Assembly Square area of Somerville, close to the Mystic River. The nearest T stop is Assembly on the Orange Line.