Boston in Winter: Things You Can’t Miss

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Visiting Boston in winter may not be the ideal time to explore the city, but I thoroughly enjoyed my time there this past December. The city if full of history, and if you dress warm enough, you can easily walk to many of the places on this list. Because of the cold weather, Boston isn’t as busy in the winter. That means less lines and more time to tour Boston! Here are things to do in Boston in winter that you can’t miss.

The Mapparium located in the Mary Baker Eddy Library boasts a three story, stained-glass globe of the world. It was interesting to go inside and check out the proximity of other countries from inside the room.

*While photos and video are not allowed, there is a photo opportunity right outside the room. Tours are every 20 minutes.

We were told the bathrooms in the library were rated the best in Boston for being interesting. I was underwhelmed. However, it was clean!

While many trek to the Skywalk Observatory at the top of the Prudential Center, we headed to the top of our hotel at the Marriott Vacation Club Pulse at Custom House. The old Custom House, authorized by President Andrew Jackson, used to be on the waterfront but due to one of the biggest landfill projects (transforming the city of Boston from hilly to flat), it is now a few streets down from the water.

When you get to the top of the Custom House, you can walk around the tower for a beautiful view of the harbor (or sunrise!). Don’t forget to check out the old clock inside the tower.

Located in the Beacon Hill area of Boston, this street is one of the last to actually have cobblestones as paving material. Since it was cold outside, we didn’t have to work around crowds to get a decent shot of the street!

First, I suggest a hop on hop off bus tour to get a feel for where things are in the city. The tour gives you a good overview of the history and present events in the city. I found the drivers to be very interesting. We used it for 2 days so that we could get to some of the Freedom Trail sites quicker. Fenway Park, Harvard, and the USS Constitution, where the trail ends, is a bit farther away than the rest of the trail.

Then, I suggest actually taking a walk on the Freedom Trail. Just follow the 2.5 mile, red brick trail that starts in Boston Common. If you get lost, just look for the bricks. SO simple for people like me that get lost easily! 🙂 There were days that I walked this trail all by myself for the exercise. Despite the wind coming from the bay, the exercise and dressing appropriately kept me warm.

The architecture in the area is beautiful! Check out Trinity Church and other area buildings.

The Massachusetts State House is the country’s oldest continually running state capital building and has a dome covered in gold.

Visit the old cemeteries of Granary, Copp’s Hill, and King’s Chapel Burying Ground where people famous in history are laid to rest, such as Samuel Adams, John Hancock, and Paul Revere.

Paul Revere’s House is the oldest remaining structure in downtown Boston. This is where Revere lived during the time he made the famous messenger ride to Lexington.

Outside the Old City Hall (now a Ruth’s Chris) is a hopscotch mosaic that commemorates the original location of the first public school in America, Boston Latin School.

The Old North Church’s steeple is the location where 2 lanterns were lit to notify the Sons of Liberty that the British troops were arriving by sea.

Ok, so maybe not real tea, but you can pretend that you are a part of the Boston Tea Party while learning all about this famous event at the Boston Tea Party Ships & Museum. We enjoyed the live reenactments and tour of a replica tea party ship. At the end, you can throw “tea” into the sea!

Located in the center of civic events that lead up to the Revolutionary War, the Old State House is one of America’s oldest public buildings. Inside, we enjoyed a tour through history of events that led up to the Revolutionary War and stood right behind the balcony where the Declaration of Independence was read for the Bostonians for the first time in 1776.

Right out front, you can stand where the Great Massacre occurred.

Visiting the USS Constitution and its museum are one of my favorite things to do in Boston in winter. I really enjoyed seeing the dry dock, learning about life onboard Old Ironsides, and hearing about its history in the interactive museum.

Visit the museum FIRST to find out how Old Ironsides got its name and if a tsunami happened when it exited the dry dock for the first time. Don’t miss the movie about the story of Old Ironsides and the setting of the War of 1812. One thing I recommend trying is climbing onto the sail that is located on the second floor of the museum. See if you have what it takes to furl the sail without falling overboard. Hint: I didn’t!

The dry dock in the Navy Yard where the USS Constitution is located.

Visitors can explore the world’s oldest commissioned warship still afloat. Just standing on America’s Ship of State that has been undefeated since it set sail in 1797, and thinking of how its fighting spirit motivated the American people at such an important time in history, made me emotional in a thankful type of way.

I found it interesting that the Navy sailors began the War of 1812 with whatever clothes they had and would acquire clothes from fallen soldiers. By the end of the war, they started buying clothes to match one another and this became their uniform. I also love how the community of kids in the Boston area saved their change so that they could keep Old Ironsides afloat.

Boston has SO many delicious places to eat. Fresh seafood, the Boston Cream Pie, and various specialty diners.

One thing I noticed quite quickly was the numerous Dunkin’ Donuts stores in Boston. It wasn’t long before I learned that the original Dunkin’ Donuts started in Quincy, Massachusetts, which is just a few minutes from Boston. (We stopped here on our Boston to NYC road trip.)

I definitely recommend a stop at Quincy Market. Here, you can find many places to eat all in one spot. I was amazed by all the food! I had my first lobster roll ever here. It was quite delicious.

Another spot I recommend eating at is Boston Burger Company. After walking around the city and making our way to the Fenway Park area, we were famished. We happened upon this creative burger joint and were so glad we did. Try their gourmet fries, a craft beer, or one of their crazy milkshakes. We were amazed by the creative design of the strawberry shortcake milkshake.

Faneuil Hall is quite the happening place, even in winter. Here, you will find many boutiques and places to shop. There are street entertainers that put on amazing shows for tips. At Christmastime, New England’s largest Christmas tree is set up here with its own light show. Horse and buggy rides are available here, too.

Cheer on either the Boston Bruins hockey team or a Boston Celtics basketball game at TD Garden. We happened to be in the city while the Celtics were playing and stopped at one of the ticket sales stores across from the arena for some good seats.

When I found out that Boston had a speakeasy that lead to a shoe store, I HAD to check it out. When I arrived at 6 Clearway Street, I walked into a staged (and sketchy!) convenience store where one can buy drinks and snacks. I had read that the secret entrance is behind the Snapple door so I opened the door and made my way into one of Boston’s best kept secrets! I wanted to video the experience, but cameras are NOT welcome.

There are a few places to go ice skating in Boston. My favorite is the Boston Common Frog Pond.

While in Boston Common, check out the Founder’s Memorial near Beacon Street.

Across from Boston Public Common is the Boston Public Garden. This is where you will find the Make Way for Ducklings statues.

Visiting Boston in winter definitely has its downfalls. Going to Boston and not getting to see a baseball game is a bummer. I was told there are tours still available. However, we just went for the photo op and will just have to go back!

I have to be honest. Visiting a library while on vacation wasn’t at the top of my plans. But, I am SO glad I stumbled upon it on my way to find the Boston Marathon finish line (located right down the road.) The library is absolutely gorgeous with beautiful displays of art and architecture. (Oh, it’s also a good place to warm up! 🙂 )

This is the place to find local and specialty items in Boston. There are so many yummy things to eat in here! We loved the apple strudel from Red Apple Farm.

While a visit to Salem in winter is NOT the ideal time, we did want to check out the area since we were so close. We took a train right to the downtown Salem area. Most of the town is closed or shorter hours for the winter so check before you go. We went to the Salem Museum and learned about the Salem Witch Trials.

Afterward, we ate at one of the downtown restaurants called Turner’s Seafood. I highly recommend it!

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