9 Fun Activities to Do in Boston from a Native

Need inspiration for wicked fun activities to do in Boston? Here are 9 great ideas guaranteed to make your trip a memorable one!

Below are 9 fun activities to do in Boston! As a Mass native, I want to provide you with the best activities to make sure you make the most of your time in this historically unique city.

Best Activities to Do in Boston

1. Explore the Freedom Trail

No trip to Boston is complete without exploring the Freedom Trail. Be sure to wear comfortable walking or running shoes, as you’ll be walking on old cobblestone for much of the trail. Learn about the fascinating history of the founding of a country and America’s fight for independence in starting the Revolutionary War. The trail meanders through many significant sites including Boston Common, the State House, the Old South Meeting House, Fanueil Hall, Paul Revere’s house, Old North Church, the USS Constitution and Bunker Hill Monument.

We recommend using Get Your Guide to connect you with local tour guides. It will enhance your Freedom Trail experience.

2. Walk along the Charles River

If the weather is cooperating, take a walk along the Charles River. This is one of the most beautiful ways to enjoy Boston. Whether you’re going to a Red Sox game, walking around Boston Common and the Public Garden, or coming from the Science Museum, the Charles River is easily accessible by foot. Another popular way to experience the Charles River (especially among tourists) is by the Boston Duck Boats. The duck boats guides will give you a history of Boston, and transform from a bus to a boat, as you tour around the city.

3. Take a ferry ride in Boston Harbor

Another special way to take in Boston and enjoy the city is by ferry. Arrive at Long Wharf, purchase tickets, and enjoy the harbor (or “harbahhh” if you want to speak like the locals). On these ferry rides, you can expect to be educated on some of the history of Boston, and the city’s fascinating relationship to trade over the years.

4. Have an Italian meal in the North End

Some of the best food in Boston can be found in the North End. Many Italian immigrants settled in this neighborhood of Boston. Here you’ll find delicious restaurants and bakeries. We recommend Giacommo’s. This restaurant is always packed. Be prepared to wait as they do not take reservations and are cash only. Other phenoenal options include Panza (just across the street from Giacommo’s), and Trattoria. For bakeries and a great cannoli, head to Mike’s Pastry, or Modern Pastry.

5. Enjoy Boston Common

In the heart of city is Boston Common, which lays claim to being America’s oldest park. The park is kept in immaculate condition. It is extremely clean and safe. From the park’s grounds, you can easily take in the State House. Have a picnic, or just walk around and take in the sights. Afterwards, we recommend having lunch at Parish Cafe and Bar. There is a delicious selection of sandwiches and delightful beverage options. For a great beer selection, check out Harpoon Beer Garden.

6. Ride the “T”

If you’re ready to live like a local and experience a bit of Boston’s working class, hop on the “T!” This is Boston’s public transportation system. In recent years, the city has made the T more accessible by adding Apple Pay options to get in and out of the turnstiles quickly. We recommend using the T to explore some of Boston’s other great neighborhoods including the South End, Back Bay, Harvard Square (Cambridge, MA) and Davis Square (Somerville, MA).

7. Attend a Celtics, Bruins, or Red Sox game

They don’t call it “City of Champions” for nothing. Boston has a very rich sports history and a loyal fan base. If you’re visiting Boston in the winter, a Bruins game is a thrilling atmosphere with fast pace aggressive hockey. The Red Sox are the oldest Boston professional sports team. Fenway Park is a marvelous traditional ballpark that you won’t find anywhere else in America. As of 2025, the Celtics are the hottest team in town, and only a couple years removed from being crowned NBA (National Basketball Association) Champions. The Patriots are unfortunately far from the city center, but tryout one of the many Boston sports bars!

8. Experience One of Boston’s Many Iconic Museums

Boston is a mecca of education with some of the highest number of colleges and universities in the world. It should come as no surprise that their museums are iconic as well. The Museum of Fine Arts hosts some of the most stunning art in the country and is a must see for anyone passionate about art. In addition, The Museum of Science is a terrific experience, especially for families. There are tons of fun activities and exhibits and one of our favorite places to spend time with our young nephews.

9. Visit an Historic Pub or Brewery

Boston and beer go together like peas and carrots. As a city full of former Irish immigrants, there are no shortage of pubs. For great traditional Irish music, visit the Black Rose and enjoy a Guinness. One of our favorite local Boston breweries is Harpoon Brewery located in the Seaport district. At the end of the Freedom Trail, stop in at Paul Revere’s old stomping grounds at Warren Tavern, and you can have fun imagining the Patriots plotting their plans for independence.

We hope you enjoyed these 9 fun activities to do in Boston!

If you’re curious to see where we stayed in Boston, check out our post on “Where to Stay: The Revolution Hotel.” Enjoy exploring!