Winter

Top Best Things to Do in Boston in Winter

1. Skate or Sled in Boston Common, 2. Walk the Freedom Trail, 3. Admire the View from the Prudential Skywalk Observatory, 4. Explore the Museums, 5. Drink Hot Chocolate, 6. Tour the Taza Chocolate Factory, 7. Watch a Play in the Theater District, 8. Shiver While Frostbite Sailing in Boston Harbor, 9. Shop 'Til you Drop at the Prudential Center, 10. Visit a Holiday Market. Don't let the cold stop you from visiting in the new year. In addition to being the quietest and most affordable, Boston is at its most gorgeous during the coldest months. There are so many fun things to do in Boston in winter that you'll almost forget that it's cold. Plan for your next trip with the list of the Best Things to Do in Boston in Winter below!

  1. Skate or Sled in Boston Common
  2. Walk the Freedom Trail
  3. Admire the View from the Prudential Skywalk Observatory
  4. Explore the Museums
  5. Drink Hot Chocolate
  6. Tour the Taza Chocolate Factory
  7. Watch a Play in the Theater District
  8. Shiver While Frostbite Sailing in Boston Harbor
  9. Shop ‘Til you Drop at the Prudential Center
  10. Visit a Holiday Market

Skate or Sled in Boston Common

Winter in Boston is known to bring blizzards, but locals know that seasonal snowstorms come with an upside. When flakes start to fall, folks of all ages head for the hills to go sledding and tubing.

The Boston Common Frog Pond is the perfect place to unleash your inner Michelle Kwan or simply try to finish a lap without falling. This popular pond is home to a skating school, offers skate rentals, including devices fashioned like seals to help young children (or wobbly adults) in finding their balance, and is located in the center of the oldest public park in the nation. Once you’re completely chilled or exhausted from landing so many triple axels, stop into the Frog Pond Café for some hot chocolate and hearty, warm comfort food. One of the best winter activities in Boston is skating on the rink, which is open from November through March. Grab a sled or a cafeteria tray and head to Flagstaff Hill if you’re fortunate enough to come during a snowfall. This is one of the city’s most well-known sledding locations.

top best things to do in boston in winter

Skate or Sled in Boston Common

top best things to do in boston in winter

Walk the Freedom Trail

One of the best sites to visit in Boston is the 2.5-mile-long red-brick Freedom Trail, even though a light dusting of snow would make it difficult to see it. Boston’s iconic 2.5 mile-Freedom Trail connects 16 nationally significant historic sites, each one an authentic treasure.

The walk starts (or ends, depending on the direction you choose to walk it) at the Boston Common and ends (or starts) at the USS Constitution and Bunker Hill. Along the walk, you will visit historic churches, meeting halls, cemeteries, and battlegrounds. The Massachusetts State State House, Old South Meeting House, Old State House, and the site of the Boston Massacre are some of the 16 most significant historic buildings that can be found along this long, twisting walk. The path also leads to Faneuil Hall, which is home to a famous market worth spending at least a few hours in. There are a ton of entertaining things to do in this historic location, such as shopping, dining, and watching a dance performance or concert. Quincy Market is also right next door.

top best things to do in boston in winter

Walk the Freedom Trail

top best things to do in boston in winter

Admire the View from the Prudential Skywalk Observatory

The Prudential Skywalk Observatory offers the most breathtaking view in Boston. The greatest time to go is in the late afternoon when you can see the sky become pink and orange as the sun sets.

One of Boston’s most popular tourist attractions is the Skywalk Observatory, which is located on the 50th floor of the Prudential Building. From its 50th-floor Skywalk, it does offer a birds-eye perspective of Boston. The Skywalk, which is entirely made of glass, provides breathtaking 360-degree views of Boston and Cambridge along with an entertaining audio tour (with a special version catering to kids). Travelers are rewarded with a magnificent, 360-degree view of the whitewashed Boston Common, frozen Charles River, snow-covered brownstones, and powder-covered streets when they visit during the winter. You can see up to 80 miles out on a clear day. You may learn about the history of the city inside, where it’s cozy and the displays are fascinating and interactive.

top best things to do in boston in winter

Admire the View from the Prudential Skywalk Observatory

top best things to do in boston in winter

Explore the Museums

For those looking for indoor activities, there is good news. Some of the oldest and best museums in the nation are found in Boston. The Boston Tea Party Ships & Museum is a must-see and unquestionably among the top attractions in Boston during the winter. Visitors can take an impressive historic trip back to 1773 at this famous floating location. You may participate in the renowned event that changed forever the path of American history at the Boston Tea Party Ships & Museum with a multi-sensory experience that includes live actors, interactive exhibits, and full-scale replicas of 18th-century sailing vessels!

Another popular destination in Boston is the Museum of Fine Arts. Visitors can look at treasures in every genre, from interesting photography to contemporary street art to ancient Egyptian sculptures. An insider’s recommendation is to celebrate Diwali in mid-November during the traditional festival of lights. Spend the day at the Boston Children’s Museum with the kids. Visit a Japanese silk merchant’s home, experiment with bubbles in the Science Playground, or make something great in the Art Lab.

top best things to do in boston in winter

Explore the Museums

top best things to do in boston in winter

Drink Hot Chocolate

A delightful cup of hot chocolate is the best beverage to warm your chilly bones. Winter tourists will be rewarded with a variety of hot chocolate options to suit their tastebuds, from too sweet to spicy to vegan.

The little but lovely L.A. Burdick Chocolates is tucked away on Clarendon Street, and wow does it smell good! Prepare to socialize with lots of people while enjoying the creamiest chocolates and the best hot chocolate around. A little-known secret: the vegan dark is equally as tasty as the milk. For your trip home, grab a bag. Even while Thinking Cup is best renowned for its coffee, you should try their French hot chocolate as well. It is made with 64% Tainori Valhorna drinking chocolate and is rich and creamy. The North End, Boston Common, and Back Bay are the three options. There are two sites for 1369 Coffee House: Inman Square and Central Square. That’s beneficial since its offerings are unique and appealing. Ever tried hot chocolate from Mexico? While the Dutch Homemade Hot Chocolate is a delicious gift to your mouth, its spicy combination of coriander and cinnamon will awaken your senses

top best things to do in boston in winter

Drink Hot Chocolate

top best things to do in boston in winter

Tour the Taza Chocolate Factory

Taza is one of the few chocolatiers in the country that makes its chocolate from scratch, starting with cacao beans. And a tour of the Taza Chocolate Factory is always present in the list of the top winter activities in Boston. Factory tours are offered to teach customers about Mexican chocolate production.

Technically located in Sommerville, this top attraction is a must-see and is 14 minute drive from Boston Common (and taste). Taza, known for its stone-ground chocolate, gives excursions to visitors every Monday through Sunday to show them how their meticulous treat-making is done. Taking kids to Taza Cacao Scout Bingo or Chocolate Story Time on a Saturday morning will win them over for sure. As the places fill up almost as quickly as your belly, be sure to make your reservations in advance. It’s difficult to leave here without buying anything, so prepare to have your wallet seduced into purchasing anything from the entire Chocolate Mexicano collection to a few bags of delectable sea salt and almond dark bark.

top best things to do in boston in winter

Tour the Taza Chocolate Factory

top best things to do in boston in winter

Watch a Play in the Theater District

Nothing like a night at the theater, complete with fancy clothing, fine eating, and live performances in a lavish setting. More than a dozen theaters make up Boston’s main theater area, which is located in the city’s center.

You can get anything you’re looking for in this glitzy area, from Broadway musicals to Christmas-themed performances to dancing performances. Visit the renowned Boston Opera House even if you’re not an opera buff. This magnificent Baroque building, a staple of Washington Street, symbolizes beauty at its best. This is where The Nutcracker ballet, a holiday season must-see, especially for those traveling with children, is performed in the months of November and December. Visit the Colonial Theatre on Boylston Street as soon as you can. The interior of the structure has recently undergone a lavish (and expensive) renovation, and it is intriguingly ornate. A lot of well-known shows have also made their debuts here before moving on to Broadway in New York.

top best things to do in boston in winter

Watch a Play in the Theater District

top best things to do in boston in winter

Shiver While Frostbite Sailing in Boston Harbor

Only passionate sailors would be willing to face Boston Harbor’s icy waters from November through April. Conditions on Boston Harbor can be very challenging for newbies, especially if you aren’t used to shifty puffy winds. So it appears that many people are eager to take that action. If you’re one of them, wrap up and go to the Lewis Warf or Winthrop Frostbite Sailing Club in Boston, both of which are close to Logan Airport.

You’ll be rewarded with an unparalleled view of the city in addition to the excitement you’ll experience as the chilly breeze touches your skin. a novice at sailing? Not to worry. The sailing school offers instruction, but you should dress warmly. Not willing to take the chance of getting wet or suffering frostbite? Look up race times on the websites of the sailing centers, then grab a cup of something steamy to keep your hands warm and head to the harbor to watch from the dry shore.

top best things to do in boston in winter

Shiver While Frostbite Sailing in Boston Harbor

top best things to do in boston in winter

Shop ‘Til you Drop at the Prudential Center

The Prudential Center, sometimes known as “The Pru” by locals, won’t let you down whether you’re looking for holiday presents or want to spend the day in a comfortable indoor setting. Located in the heart of Boston’s historic Back Bay, the landmark Prudential Center is a 3.2 million SF mixed-use urban center comprised of 2.6 million SF of office space and 620,000 SF of retail space.

With over 60,000 visitors a day, The Shops at Prudential Center is ranked among the top 5 shopping centers in the nation by Women’s Wear Daily, and is only steps from Boston’s famed Newbury Street, Fenway Park, museums, subways, and the best of Boston culture. Here offer all the well-known names, including Ann Taylor, Saks Fifth Avenue, Lululemon, L’Occitane, and Sephora. Even a Peloton bike or a stack of books are available from Barnes and Noble.When it’s time to eat, enjoy one of the numerous delectable eateries. Our favorites are Sweet Green for a healthy break (the crispy rice bowl is delish) and Wagamama for noodles (their juices and dumplings are wonderful). Eataly offers visitors a three-floor Italian dining and shopping experience.

top best things to do in boston in winter

Shop ‘Til you Drop at the Prudential Center

top best things to do in boston in winter

Visit a Holiday Market

Without a market, what would the holiday season be? The Boston Winter Holiday Market, one of Boston’s most well-liked events, draws close to 100,000 visitors annually to the City Plaza Government Center. It starts the day before Thanksgiving and stays open until New Year’s Eve, providing visitors with the perfect location to find the most unique holiday gifts.

You’ll discover a ton of delicious delicacies to satisfy your belly, as well as a wide choice of festive shows and other entertainment to up the fun factor at this top winter destination in Boston. The market’s unique shops are situated in adorable European-looking “chalets”. Enjoy visiting markets and craft shows? Early in December, a Christmas Fair is held at Copley Square’s Old South Church. Simply admiring the building’s stunning architecture is reason enough to go. Another one-day event that takes place at the Ben Franklin Institute in the first week of December is the South Boston Holiday Market. There aren’t many places where you can buy food, jewelry, or clothing with such avant-garde designs.

top best things to do in boston in winter

Visit a Holiday Market

top best things to do in boston in winter

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