Spend a Long Weekend in Boston
As a Massachusetts local, it always excites me when people visit or move to our state’s capital. I’ve definitely flirted with the idea of moving back to Boston because of how charming and exciting the city can feel. If you’re a big fan of U.S. history there’s probably no better city you can be than Boston (although Washington, D.C. may have something to say about that). Here’s a great plan for a long weekend in the city.
Day One: Walk through the local history & catch a ballgame
You’re going to dive right into what Boston is most famous for by taking a morning & afternoon walk along the Freedom Trail. The full length of it is around 2.5 miles, and the walk covers many of the historical sites in the city. You can do an organized tour, but I prefer just walking it at my own pace and stopping whenever something particularly interesting comes up. My favorite spots on it are the site of the Boston Massacre and Old North Church. There are markings along the trail to keep you on track as well! I suggest stopping whenever you get hungry or thirsty along the way, and enjoying the route!
Next I suggest you make your way over to the Back Bay neighborhood to check out some sites in this established area. In particular, I enjoy going to the Mapparium, an exhibition where you can actually step inside a globe and see the world all around you. It’s a great attraction for both adults and kids. Additionally, the Prudential Center is a popular shopping center in the area that serves as a great hangout place.
To close your day, try to go see the Boston Red Sox play at Fenway Park, if there’s a game happening. The stadium is the oldest ballpark in the country, and it’s filled with passionate fans and incredible history. If you’re going to go to one baseball game in the US, I highly suggest you see the Sox play!
Day Two: Enjoy some Museums and Good Eats
Today is a great day to check out some more historic food spots in the city, so I suggest you start with a trip to Faneuil Hall. It served as a meeting place for revolutionaries and was used as a government building throughout Massachusetts’ history. If further interested, head inside the building to check it out even further!
Right next to Faneuil Hall is Quincy Market, a food hall that’s been operating since the 19th century. There are a ton of different shops for you to grab a bite at and enjoy the live music + performances in the area. Don’t miss it!
Spend the rest of your day checking out a museum or two in Mission Hill. I’d personally recommend the Isabella Stewart Gardner Museum, an art museum that is mostly famous for stolen paintings in the 1990s. Not often do you get a chance to learn about an actual heist that took place, so go visit it. Alternatively, the Museum of Fine Arts is in that area as well and continues to be a popular option for locals + tourists alike.
Wrap up your day in the area with some dinner at Lolita Mexican and ice cream at Toscanini’s, two popular and delicious spots in the city. Things in Boston tend to close on the earlier side, but Seaport and the Theatre District are popular neighborhoods with bars and clubs to dance the night away.
Day Three: See the University scene and Enjoy the Waterfront
We think you should start your final day in Boston by heading back to college! Harvard and MIT are both located in Cambridge, separated from Boston by the Charles River. A popular running route is along the river through Cambridge, so if you want to get some exercise in on your way to the schools, be my guest! It’s really awesome to see these historic and prestigious universities up close, because their architecture and lawns are amazing to walk around. Tatte Bakery is a popular dining option for brunch by the universities.
Head out of Cambridge to Boston’s Seaport neighborhood, an up-and-coming area with a lot of development. It gives fantastic water views of the main channel, and it is generally a fun place to walk around. I personally like going to the Trillium Brewing Company in Fort Point, as they have incredible IPAs with awesome outdoor seating. Seaport is a great area to kick back with a beer and just watch the boats sail by on your last day in the city.
To close out your day, get some authentic Italian food in Boston’s notable North End neighborhood. Bencotto and Mamma Maria are two popular options in the area, but you really can’t go wrong with any dinner option here! And I know it has calls of being overrated, but I really do think Mike’s Pastry is a must-do to finish the night; their desserts are just too good to pass up on!
Anything you think we missed for Boston sights? Let us know!
