Winter feels great in Boston. The snow adds extra allure to its cobblestone streets, legendary American Revolution-connected sights, and atmospheric parks. It will be chilly and windy here, and you can get days where snow falls without end. But the abundance of exciting indoor attractions, cozy cafes, and a diverse culinary scene save the day. And you’re saving money too, December to February is the cheapest time to visit The City on a Hill. We’ve prepared the top things to do in Boston in winter and have a fantastic experience in one of America’s oldest cities.
Go Ice Skating
What Is It? Ice skating is an obligatory winter pastime for Bostonians. Skating rinks pop up around the city bringing festive joy to the locals and residents. The must-visit is the Frog Pond on the Boston Common, a super central and iconic stop. Other cool spots are Kendall Square rink in Cambridge and Jack Kirrane rink in Lars Anderson park.
Why Do It? Whether you’re looking for family fun or a date spot, you can’t go wrong with good old ice skating. And historic Boston would be happy to deliver the most charming time on the rink.
Good to Know: The ice skating season opens at the end of November and lasts until the beginning of March. Be sure to wear warm clothes, New England outdoors can get quite cold.
Taste Italian food in North End's Little Italy
What Is It? Boston’s Little Italy is a quaint central neighborhood in the North End. Rivaled only by New York’s counterpart, this district is defined by numerous Italian eateries serving the best of the best of the Apennine cuisine (with a Boston flair). From grab-n-go pizza windows to fine dining institutions, you can’t go wrong with this neighborhood.
Why Do It? Winter calls for long restaurant evenings savoring delicious food. You’ll be spoilt for choice with the meals to try in Little Italy which is also among the most picturesque places in the city.
Good to Know: It’s always great to have a fine pizza or pasta, but it also pays off to go further as Italian cuisine is truly limitless. Head to Mike’s Pastry for sweet Sicilian cannolis, Bova’s Bakery has a superb selection of cookies, and Mamma Maria serves a diverse regional seafood-heavy menu.
Hit the Slopes of the Blue Hills Ski Area
What Is It? Blue Hills is the closest ski resort to Boston. You only need 20 minutes to reach it from Downtown. An ideal choice to get some family-oriented winter fun, it has an area of 60 skiable acres, a vertical drop of 309 feet, 16 trails, and a terrain park.
Why Do It? With such close proximity to the city, you will be enjoying the fresh air on the slopes throughout the day and cozy up in the Boston cafes by the evening.
Good to Know: Daily snow passes prices start from $30 and depend on the day and the time.
Marvel at Sea Creatures at New England Aquarium
What Is It? Central Wharf-located New England Aquarium is the biggest on the East Coast. A visit here takes you to a magical world of water dwellers. You kids would love a chance of seeing so many gorgeous animals (15 000 to be precise) inhibiting a whopping 75 000 square feet of exhibition halls.
Why Do It? New England Aquarium is hands down one of the most impressive indoor attractions of Boston which makes it a perfect choice for winter exploration.
Good to Know: The 200 000-gallon Giant Ocean Tank is an unmissable sight with Caribbean coral reef animals. If you love penguins, there is a big exhibit that is home to many African southern rockhopper penguins.
Catch an Ice Hockey Game
What is it? Two words: Boston Bruins. One of the most venerated and decorated teams in the NHL, it is fortunate to call this city home. And you can’t miss watching them play at TD Garden.
Why Do It? This city has a fame for being totally sports-obsessed. One of the best things to do in Boston in winter would be to see ice hokey frenzy and the local cheering traditions yourself. The Boston Bruins game is a great option.
Good to Know: Keep an eye out for the game schedule on the NHL website. And be sure to book your tickets beforehand, it’s hot property in Boston.
See a Ballet at the Boston Opera House
What is it? Located at 539 Washington St, Boston Opera House is one of New England’s most celebrated venues. Opened in 1927, it boasts elegant Belle Epoque-inspired interiors and a definitive cultural program. Boston Ballet calls it home and regularly supplies Bostonians and guests with fantastic performances.
Why Do It? What can be a more fitting choice for a chilly winter evening than suiting up and attending a performance at a world-renowned art venue? Surround yourself with beauty and opulence here and get an inspirational fix.
Good to Know: If you’re not in for a full-scaled performance, you can still get inside. There is a special historical tour organized by the Opera giving you an insider look into an exciting story of the venue’s fate.
Go on a Tour of the Legendary Fenway Park
What is it? One of the most popular things to do in Boston in winter (and all year round really), getting inside the Boston Red Sox home would be a hit among baseball lovers. Full of quirks, anomalies, and countless sports anecdotes, the 1912-opened Fenway Park is a righteous Boston must-see sight.
Why Do It? This easygoing, affordable, and entertaining excursion takes only 1 hour of your time but lets you take an immersive look at one of America’s most exciting arenas. If you’re a baseball buff it will bring a spectacle of emotions, if not, it’s still a cool change from the classic attractions.
Good to Know: The best way to experience Fenway Park in its full glory mode is by attending a Red Sox game. The end of February is when the season starts so hurry up with the tickets.
Celebrate New Years' Eve with Boston’s First Night
What is it? December 31st is a special date and Boston knows how to throw a good party. Free First Night celebration brings together events, activities, ice sculptures, and light displays in Copley Square and Back Bay.
Why Do It? Celebrating New Years’ Eve with the whole city is one of the bucket list things to try. Doing that in electric Boston is a fantastic idea.
Good to Know: Check out the schedule for the First Night on the official website of the event. January 1st sees the city lightening up with a spectacular display of Boston Harbor Fireworks so be sure to stick around to witness the show.
Dine at Historic Restaurants
What is it? Old World vibe is alive and well in Boston and the restaurant scene proves it. Only in the state capital of Massachusets that you find so many eateries that have been in operation for centuries and boast splendid interiors and unparalleled atmosphere. And winter would be a perfect season to get the most out of exploring them.
Why Do It? Savoring exquisite food under the chandeliers in a hall where the US Presidents used to dine while snowflakes fall outside. Does it get better than this?
Good to Know: Charlestown’s Warren Tavern has been around since 1780 and still runs strong delivering an old pub atmosphere. Caffe Vittoria is for a coffee and gelato fix in a European setting. Union Oyster House is a 19th-century seafood-serving institution that locals love. And you simply can’t miss having a bit of the Boston Cream Pie at long-running Parker’s Restaurant.
Feel the Old World Opulence at The Langham
What is it? Peak Boston 5-star hotel set in the former U.S. Federal Reserve Bank. Combining sumptuousness and character, it’s among the best upscale accommodation choices in the city. Located in the heart of a Financial District, it gives you a chance to feel the vibrance of the Downtown while being a short walk away from all the attractions.
Why Do It? The colder months see prices slightly drop and it’s the best timing to treat yourself to a five-star Boston stay. With The Langham you’re playing it safe, it’s a rising star of the city’s elegant hotels and delivers a superb central stay.
Good to Know: What can be better than lounging in a 40-foot indoor heated lap pool when it’s cold outside? The hotel’s wellness proposition is on point and you have to take advantage of it.
Get a Taste of Beacon Hill Upscale Living
What is it? Beacon Hill with its elegant townhouses, central location, and the enticing historic atmosphere is the epitome of Boston’s good living. Why not immerse yourself here for your next trip to the Hub? With this Airbnb, you’re getting a beautifully renovated apartment set in a historic Beacon Hill house.
Why Do It? Having Beacon Hill as a base lets you explore Boston hassle-free. Boston Common, Museum of African American History, Massachusetts State House, Charles River Esplanade, and Public Garden are all within walking reach.
Good to Know: Airbnb is set in an old 4-story brownstone townhouse and features a fully equipped open kitchen, two bedrooms, a spacious living area, and high ceilings. It would be a perfect choice for a family of up to 5 people.
