A Day in Boston, Massachusetts

Boston is a historic city, and America as we know it today was largely influenced by historical events originating here. It’s not all just history though – Boston is a educational hub, has vibrant nightlife, excellent restaurants, and sports teams with die-hard fans. So here’s how to spend a day in Boston.

The Freedom Trail

An ideal way to start off a day in Boston is with a walk along the 2.5 mile long Freedom Trail. The Freedom Trail is a route full of historical information through downtown Boston that takes you to 16 important historical sites in the city while teaching you the city’s role in the founding of the country.

The Freedom Trail is easy to follow as its largely marked with brick, but if you prefer to go the guided route like we did, the Freedom Trail Foundation offers 90 minute tours of the trail that passes through 11 of the 16 historical locations. To see tour times and book a tour, click here.

Massachusetts State House

One of the first sites along The Freedom Trail is the Massachusetts State House. The Massachusetts State House serves at the state capitol and seat of government for the state of Massachusetts and is situated opposite Boston Common.

What really makes it significant though is that the State House is built on land once owned by John Hancock, Massachusetts’s first elected governor. As well, the dome we see today was covered in copper in 1802 by Paul Revere’s Revere Copper Company.

Sam Adams, Granary Burying Ground

Also along the Freedom Trail is the Granary Burying Ground, the third oldest cemetery in Boston founded in 1660. It is the final resting place of many notable Revolutionary-war era patriots, including Paul Revere, and three signers of the Declaration of Independence: John Hancock, Robert Treat Paine, and Samuel Adams.

Although the cemetery has 2,345 grave-markers, it’s estimated that as many as 5,000 people are buried in it. Try not to keep that in mind as you walk around!


Fanheuil Hall and Sam Adams statue

Our next stop in Boston was one of the city’s most iconic, Fanheuil Hall, which has been a marketplace and meeting hall since 1743. The hall has played an important role in American history as the site of several speeches by Sam Adams and James Otis encouraging independence from Great Britain.

It would make sense then, that Sam Adams, a leader in the American Revolution who later became Massachusetts state governor (and namesake for the beer of the same name!), would live on in statue form in front of Fanheuil Hall.

Inside Quincy Market

Adjacent to Fanheuil Hall is Quincy Market, which first opened in 1826 and is named after the second mayor of Boston, Josiah Quincy.

Quincy Market was our lunch stop of the day, and is a great pick for an affordable meal in often-pricey Boston. Within the market are several eateries, restaurants, and shops – there’s no shortage of options here!

Paul Revere House

After lunch at Quincy Market, we decided to continue along to one of the Freedom Trail sites that our walking tour didn’t cover – the Paul Revere House. Built in 1680, the Paul Revere House is the oldest house in Boston’s North End, and where Paul Revere lived with his family on and off from 1770 to 1800.

For those of us who haven’t brushed up on American history lately, Paul Revere is best known for his “Midnight Ride” to alert the colonial militia to the approach of British forces before the battles of Lexington and Concord – the first military engagements of the American Revolutionary War.

After Revere’s time living in the house, it switched hands and served a variety of purposes until 1902, when his great-grandson purchased the building to prevent demolition.  Today, the house is maintained by the Paul Revere Memorial Association and open to the public. Prices for entry to the house can be found here.

Little Italy, North End

Boston’s North End neighborhood of Little Italy is the city’s oldest residential community, where people have continuously inhabited since it was settled in the 1630s. The area was especially popular with Italian immigrants, whose restaurants still influence the neighborhood today. Not one to pass up a good Italian bakery, we headed to Modern Pastry for a cannoli. Mike’s Pastry, down the street, is also a popular gelato and cannoli destination.

While the North End is compact enough to easily explore on your own, I have previously done a Free Tours by Foot walking tour of the area and recommend it.

Fenway Park

Last but not least, no trip to Boston is complete without checking out the beloved Fenway Park, home of the Boston Red Sox since 1912. I was fortunate enough to go inside the stadium a few years ago for the highly anticipated match up of the Boston Red Sox and New York Yankees, but if actually watching a game isn’t in the cards for you, stadium tours are also offered multiple times daily.

After our time at Fenway Park, we wrapped up our day in Boston by walking over to the Back Bay neighborhood where we enjoyed dinner and drinks at Piattini.

Harpoon Brewery beer flight

With more than a day…

  • The Harpoon Brewery is an ideal place to go for a drink or if the weather is downcast. Their pretzels are delicious and you can’t go wrong with a Harpoon beer flight!
  • The Black Heritage Trail is a walking tour that explores the history of Boston’s 19th century African American community. For a trail map and tour times, click here.
  • Enjoy a skyline view of Boston at the Top of the Hub restaurant and bar.
  • Head 45 minutes out of the city to Salem, Massachusetts, home of the infamous late 1600’s Salem witch trials

Have you been to Boston? What’s your favorite attraction in the city?


3 thoughts on “A Day in Boston, Massachusetts

  1. I love Boston! In 2010 my husband and I spent part of our honeymoon there before heading to Maine. The Freedom Trail is so fascinating; it really makes history come alive. I also liked the Old North Church and food in Little Italy.


    1. Agreed – it was really interesting to learn so much about how the country started. My British boyfriend may have been a bit less enthused about the ‘kicking the British out’ part though – haha! We also continued to Maine (Ogunquit and Portland) on our trip so I’ll be writing about that soon.

      Liked by 1 person

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