Far and Familiar

10 Things to Do in Boston (Even in Winter!)

Boston Blogger City Guide

This post is originally published on The Lady Project Blog. 
Words & photos by Janet Mesh. 

Boston is the birthplace of our nation

brimming with revolutionary history, culinary traditions, reputable academic institutions, and locals known for their strong accents.

From the cobblestone streets of the North End to the stunning views from the Top of the Hub, there’s never a dull moment in Beantown.

Born and raised in Boston, I’ve enjoyed uncovering the cities popular and off the beaten path sites, activities, and restaurants. With 11 neighborhoods to explore and a walkable downtown area, there is so much to explore in this city. Here’s my list of the top things to do in Boston, even in winter!

Wander through the Boston Common and Public Garden

The Boston Common and Boston Public Garden are two of my favorite places in Boston.
Located adjacent to one another and in the heart of the city, these green spaces are easily accessible. Boston’s famous watering hole, The Frog Pond, is located in the Common. In the summer, children rule the pond and splash around in the ankle-deep water. In the winter, the pond transforms into a skating rink!After showing off your best Michelle Kwon impersonations on the ice, wander over to the Boston Public Garden, famous for the ducklings, swan boats, willow trees, and the bench as seen in Good Will Hunting.

Boston Public GardenDine out at one of Boston’s great restaurants

Boston’s restaurant scene is booming, with new and hot establishments popping up all over the city. From the Back Bay to the North End and south to Dorchester, your foodie heart won’t have a hard time finding a great meal or two after a day of exploring.

My favorite restaurants include Silvertone, dBar, Toro, Parish Cafe, Figs, Lolita’s, Panza, and Ester. You can also check out popular, more expensive restaurants at a lower price in March during Boston’s Restaurant Week!

Walk around the Sugar Bowl at Castle Island

The Sugar Bowl is the walking and biking path built along and in the harbor at Castle Island in South Boston. You’ll need to bundle up if you come in the winter, but the views of the Boston skyline are well worth it! Castle Island is home to Fort Independence which was used as a military training site during the Civil War. This is a very popular spot in the summer months since its on the ocean and has plenty of green space for a picnic or to fly a kite. The take-out restaurant, Sullivan’s, has some of the best fries and soft-serve ice cream in the city. Don’t believe it? The line out the door that pours into the parking lot on summer days prove it.

Castle Island Sugar Bowl View

View of the Boston Skyline from the Sugar Bowl

Admire art at the Isabella Stewart Gardner Museum

In 1990, 13 pieces of art valued at $500 million were stolen from the museum and has never been recovered.  Luckily, Isabella Stewart Gardner collected a multitude of master and decorative arts, which is viewable at this museum. The building’s architecture is stunning with a gorgeous courtyard at its center. Fun fact: if you’re name is Isabella, then you will receive free admission to the museum! They also offer free admission on your birthday.

Treat yourself at the TAZA Chocolate Factory

Learn how this delicious, Mexican treat is made right here in Boston! TAZA Chocolate is stone ground chocolate made from Mexican cocoa beans. Public tours are offered 7 days a week in their factory and reservations must be made in advance. While touring the inner workings of TAZA chocolate production, you’ll be able to taste free samples. Yum!

Tour the Sam Adam’s Brewery

You’ll find Sam Adam’s on tap in almost every bar in Boston so why not see how it’s made right here in the hub! You’ll walk through the brewery, learn about their traditional four-vessel brewing process, and discover the science behind their pint glass. At the end of the tour, you’ll be able to sample some Sam Adam’s beer in their beer hall.  The best part – the tour is free!

Learn more about Boston’s original girl bosses on the Women’s Heritage Trail

Tour four century of Boston Women’s History on the Women’s Heritage Trail. The 7 different trails in various neighborhoods of Boston highlight more than 200 reputable Bostonian women, such as Abigail Adams, Louisa May Alcott, Amelia Earhart, and Phillis Wheatley. There are self-guided and regular tours. I recommend starting with the Beacon Hill self-guided tour since it is Boston’s quintessential neighborhood and located next to the Boston Common & Public Garden.

Boston Beacon HillWalk into the world at the Mapparium

And I mean literally walk into it. The Mapparium is located at the Mary Baker Eddy Library and features a three-story, stained glass globe of the world. A walkway cuts through the center of the globe giving you 360 degree views of the world as it looked in 1935.

Return to 1775 at the Old North Church in the North End

Many events in Boston sparked the start of the American Revolution, but the most important was the famous ride of Paul Revere from the Old North Church to Lexington. He warned the men of every town that “the British were coming” by sea which allowed them to be ready to fight in Lexington for the first battle of the Revolution.

The church is free to enter and tour. Outside in the courtyard, you’ll find a statue of Paul Revere. The North End is now Boston’s Italian neighborhood and a gorgeous place to walk around. After you’ve filled up on history, indulge yourself even more with a cannoli from the famous Mike’s Pastry on Hanover Street. 

Take in the view from the Top of the Hub

The Prudential Building’s top floor is a bar and restaurant that offers panoramic views of the city. Dinner is expensive here, so grab a cocktail at the bar as you admire this beautiful city. If dinner and a drink isn’t your thing, then you can also enjoy the sky-high views at the Sky Walk located on the 50th floor.

Boston Habor Skyline

What are your favorite places in Boston? Let us know in the comments!

4 thoughts on “10 Things to Do in Boston (Even in Winter!)

  1. Mary Westcott

    Janet, I will share a view of Boston written by your grandfather in 1965. He wrote it for a meeting of Medical Group Adminiatrators who were having a convention in Boston. You have a similar writing style. He would be proud of you. Love, Nana

  2. Lisa Macero

    Hi Janet and David…One of my favorite things to do in Boston is the harbor walk that takes you all over the waterfront area including Charlestown. Once in Charestown stop in at Pier 6 for the view and a cocktail. You can also hop on the MBTA water shuttle for an inexpensive short boat ride.

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