DESTINATIONS

What to do in Boston Depending on Your Length of Stay

Recently, R and I spent a day in Boston, Massachusetts. Now one day may not sound like much, but even a short amount of time in Bean Town is better than no time at all and I am going to share with you some tips on what to do in Boston based on your length of stay.

Captain Jackson's Boston Freedom Trail
R enjoying a piece of history on the Freedom Trail in Boston.

I love Boston. It is my favorite east coast city by far, and I always jump at the chance to visit. I was first introduced to the city back in high school. It was my first time to the east coast and although I have been back east many times now and have visited all of the major cities, Boston remains my favorite. And it is not just the city I love; the entire northeast is a beautiful part of this country with so much to do and see.

But back to the city itself…sometimes my visits are short, like this most recent one. Others are longer. Whether you plan to spend a couple of hours or a couple of weeks in Boston, there is no end of things to do. The city is swamped in U.S. history, great places to eat, and fascinating neighborhoods. Below are my suggestions for things to do, based on your length of stay.

One day in Boston

If you have only got one day, make sure you do the following:

1. Walk the Freedom Trail

Obviously, you must walk the Freedom Trail. It is a 2.5 mile path through downtown Boston passing by 16 historic locations. It is easy to follow. Simply look for the red line, marked with either brick or paint, that runs through the city. You can buy a map at the visitor’s center and even sign up for a tour, or you can do what we did and download a self-guided tour (there are several online). Most of the sites are free, but a few will charge admission. If you are short on time, you may have to pick and choose where to spend your time. The time it will take you to walk the entire trail depends on how much time you spend at each site.

I have enjoyed the Freedom Trail many times. Every time I walk it, I learn (or relearn) something new. It is a wonderful way to experience U.S. history as well as Boston. A word of warning: there will be tourists. Sometimes there will be a lot of them lining up and standing in your way. They are unavoidable. But if you visit the trail sometime other than the middle of the day, you will have better luck. Also, check out our post on tips for dealing with tourists.

Freedom Trail, Boston, red brick
If you look at the ground, you can see the red brick that makes the Freedom Trail. If you look at the top, you can also see R’s killer photography skills at work.

2. Eat clam chowder

I do not visit Boston (or the surrounding area) without enjoying a bowl of New England clam chowder. I do not have a favorite place I like to go. Being from Idaho, it all tastes good to me! But there are plenty of articles out there with recommendations for the best chowder in Boston. I just recommend you get some because it tastes so darn good.

Boston clam chowder
Eating New England clam chowder in Boston. Tasty!

3. Visit Faneuil Hall Marketplace

Yes, this place can be a little overwhelming. But there is always something happening at Faneuil Hall. There are shops and restaurants and you can even get a stamp in your National Parks Passport here. If you are short on time, you can find almost everything you need in this one location.

Two-three days in Boston

If you have got a couple of days, make sure to check off the above items, but then add on the following:

4. Catch a game

If you are lucky, the Red Sox will be playing a home game during your visit. Watching a game at Fenway Park is the ultimate Boston experience. There are also the Celtics and Bruins. Either would make for an entertaining experience, especially if the home team wins!

Boston Celtics stadium outside
A look at where some sporting entertainment can be found in Boston.

5. Explore Boston’s neighborhoods

Boston’s neighborhoods have distinct personalities and are worth exploring. Even though I could never afford to live there and I find it a tad pretentious, I love walking around the Back Bay and poking into its shops. The North End and Beacon Hill also make me very happy. And on this most recent trip, R and I discovered Charlestown while heading to Bunker Hill Monument (not following the Freedom Trail). We both commented on the cute houses and colors. It is only by walking around and exploring that you can fully appreciate the personalities of Boston’s neighborhoods.

Boston funny sign Freedom Trail
Funny sign while walking the bridges of Boston.

6. Tour the Samuel Adams brewery

Touring the Samuel Adams brewery seems apropos when one visits Boston, especially if you like beer. The tour is free, but they suggest a $2 donation to benefit local charities. Obviously, you must be 21. Tours last about one hour and they do not take reservations. I would avoid Saturdays is possible.

7. Eat at Cheers

Eating at Cheers is an incredibly touristy thing to do. But it is also a lot of fun and something I recommend you do at least once. However, try to visit the iconic Boston landmark during a slow time.

8. Get dessert in Little Italy

Boston’s North End, or Little Italy, hosts some of the city’s oldest buildings and is a maze of narrow streets. It almost feels like you have stepped back in time. You will walk right through it as part of the Freedom Trail, but it is worth some extra time if you have it. There are wonderful Italian restaurants, pastry shops and delis around every corner. It is one of my favorite neighborhoods in the city.

Boston historic cemetery
Visiting a historic graveyard in Boston.

A week or more in Boston

If you have a week or more, after you have accomplished everything above, you can get out of town and see the following:

9. Walk around Harvard University

It is easy to get from Boston to Cambridge—take the Red Line and ride it for 25 minutes. Harvard University is the United States’ oldest institution of higher learning. Established in 1636, this Ivy League school is one of the most well-known universities in the world. The campus in Cambridge is also really pretty. If the weather is nice, I definitely recommend a visit.

10. Take a train to another town

There are so many great towns just a train ride away from Boston and they make excellent day trips. Salem, Massachusetts, is one good example. Not only is the town adorable, but there is that whole witch trials event that took place there and the town features it well. Simply take the Newburyport/Rockport Line and 30 minutes later, you will be in Salem. If you want to explore a little further, stay on the Newburyport/Rockport Line and ride it to Rockport, Massachusetts. The town is surrounded on three sides by the Atlantic Ocean and hosts an array of Instagram-worthy photo opportunities. The train ride alone is worth the effort in my opinion. It will take a little over an hour, but you will move along the coast and travel through idyllic coastal towns like Manchester-by-the-Sea and Gloucester.

Whether you get out by traveling north, south or west (or east if you want to go whale watching or spend some time on the ocean), you will see some beautiful country and it will only add value to your trip to Boston.

Boston USS Constitution
Lots of history lessons to be had in Boston.

Conclusion

It you have not been to Boston yet, put it on your bucket list. If you have visited Boston before, put it back on your bucket list. There is so much to see and do there, it would take a lifetime to explore it all.

A couple of minor notes:

  • Boston is compact and very walkable, but wear good shoes. You will spend a lot of time on your feet.
  • Fall is my favorite time to visit Boston because the weather is perfect and everything is so beautiful. Boston experiences all four seasons. It can get very cold and it can get very hot. Be prepared for whatever time of year you will be traveling there. It rained the day R and I visited. Luckily, we had raincoats and umbrellas so the wet did not slow us down at all.
  • However, it is also a busy time to visit Boston. Thanks to the famous foliage, there will be many tourists. I guess you have the good with the bad.
Boston cemetery Pinterest
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