The Best Things to Do Alone in Boston

Boston is perhaps one of the greatest cities to explore for a solo trip because there are plenty of things to do alone in Boston. You have the historic Freedom Trail and plenty of unique neighborhoods, from Back Bay to Charlestown, to explore

It can be overwhelming to plan a solo trip to Boston, especially in one massive and iconic city. Luckily, I have firsthand experience from taking my own solo trip to Boston.

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I completed 28 activities in the historic town in three days, and I only spent $170 for my Boston solo trip. See my budget breakdown at the end of the article. 

Listed below are all the things I did alone during my three days in Boston. I listed my activities chronologically so you can start each day at the first location and continue from there. 

Table of contents:

This post may have affiliate links. I receive a small percentage if you book a hostel or attraction through my recommended links. This is at no extra cost to you and helps me reach my goal of becoming a full-time digital nomad. 

Is It Safe to Solo Travel to Boston?

Boston is a very walkable, compact city, making it ideal for solo travelers. The city is known for its low crime rates, so it is one of the safest cities in the U.S. for solo travelers.

However, you should exercise caution when walking at night. If you are a female solo traveler, it is recommended to walk in a group at night. If you take the subway in Boston, watch out for pickpockets, especially on the Green Line.

Where to Stay During Your Boston Solo Trip

I stayed at HI Boston during my Boston trip. I was very impressed with this hostel. They have a great, modern kitchen. They have plenty of tables and couches for chilling and getting work done. 

Each room has a large locker, but make sure to bring your own lock. The hostel is also in a convenient location, where you are close to most of the city’s main attractions. 

If you want to spend under $50 per night on accommodation, I highly recommend staying HI Boston. It is one of my favorite hostels in the entire country.

1. Go to Fan Pier Park for Sunrise or Sunset 

Begin your Boston trip at a place with an iconic city view. Fan Pier is at the heart of the harbor and overlooks Boston’s main city center. 

Noah’s Take: I arrived in Boston on an Amtrak train and got off at Boston’s South Station. It was a short walk across the Summer Street Bridge to the park. 

2. Relax at the Porter Square Bookstore on Your Boston Solo Trip

The Porter Square Bookstore is a cute, independent bookstore close to Fan Pier Park. 

Noah’s Take: It might be the perfect place to warm yourself up if you visit Boston during the winter months, as I did. 

3. Get Groceries at Trader Joe’s Near Seaport Blvd

I conveniently found a Trader Joe’s in Seaport after returning to the city center. I know this is a controversial opinion, but you can save a lot of money. 

Noah’s Take: Buy a few sandwiches and protein bars, then skip a few meals. Your wallet will thank you, and Trader Joe’s has a good selection of ready-to-eat foods that are exciting enough to make you feel like you are on vacation. 

4. Begin Day 2 at Acorn Street in Beacon Hill

Acorn Street is the most “Instagrammable” place in Boston, arguably. It is one of my favorite things to do alone in Boston if you visit early in the morning before the crowds start to come.

Step back in time and visit Beacon Hill’s iconic cobblestone streets and row houses. This neighborhood is one of the most expensive areas in Boston.

5. Walk down Charles Street and take the train to Harvard 

After a visit to Acorn Street, you can easily access Charles Street, which is lined with cafes and boutiques. In 7 minutes, you can find the Charles/MGH Subway Station. 

Take the Red Line. It will cost about $2, and you will reach Harvard. 

Noah’s Take: I easily got a round-trip ticket to Harvard at the station using the ticket machine, so there is no need to worry about this process, but if you want to be extra prepared, read this beginner’s guide to the subway from the MBTA.

6. Pretend to Be a Student at Harvard

If you are alone in Boston, you should visit Harvard and be a student! It is fun to explore this historic college at your own pace and live your Harvard fantasy, but remember, this is a college, not a tourist attraction. There are students here trying to learn. 

Noah’s Take: Tourists alike flock to the Johnston Gate and Sever Hall, but there is no need to plan out the exact spots you need to visit on campus. However, I do recommend visiting The Harvard Museum of Natural History. I did not make it on my trip, but it gets rave reviews. 

7. Take in Views of Trinity Church and Copley Square on Your Solo Trip to Boston

Trinity Church is considered one of the country’s top 10 buildings by the American Association of Architects. It is also a great place to begin a walking tour of Back Bay, one of Boston’s most famous shopping districts.

Right across from Trinity Church is Copley Square, where you can find sculptures and skateboarders. In Back Bay, you will also find the Boston Public Library, Old South Church, and the Hancock Tower. 

8. Visit the Stunning and Free Boston Public Library

The Boston Public Library is known as one of the most gorgeous libraries in the country. Visiting libraries is one of my favorite things to do alone in any city!

This is a library, not a museum, but you will find murals, vaulted ceilings, and the most-see Bates Reading Room. 

Noah’s Take: Pay extra attention to the library’s hours.

Here are the library hours:

• Monday through Thursday: 9 a.m. to 8 p.m.
• Friday and Saturday: 9 a.m. to 5 p.m.
• Sunday: 11 a.m. to 5 p.m.

9. Window Shop Around Newbury Street in Back Bay

Back Bay is known for being fashionable and full of specialty shops. It is even known for being one of the most expensive streets in the world. 

Noah’s Take: Since this is a low-budget solo trip to Boston, I only spent a little bit of time shopping here. It was more interesting to walk the street and watch pedestrians fill row houses that were converted into luxury shopping storefronts. This is not your average shopping street. 

10. Get Authentic Boston Cuisine at Summer Shack at a Reasonable Price

It’s no surprise that one of the things to do alone in Boston revolves around seafood! Boston is known for its seafood. After exploring Back Bay, I recommend heading to Summer Shack. This is an excellent place to eat staple Boston seafood without breaking the bank.

Noah’s Take: The Baked Oyster Rockefeller I bought for $16 was amazing. However, the Griddled Cornbread wasn’t my favorite. 

11. Picnic at Golden Hour at the Charles River Esplanade 

Picnics are a great way to enjoy your solo trip to Boston. On the banks of the Charles River, near Back Bay, you will find the Charles River Esplanade. This park is a great place to walk and people-watch. 

Noah’s Take: Sometimes, eating alone at a restaurant can be intimidating. So, I took my Summer Shack order and walked 20 minutes to the Charles River Esplanade.

I completely loved the scenery and watching the sunset on the Charles River. Let me clarify: there is nothing wrong with eating at a restaurant alone! However, it can be more enjoyable to eat outside under golden light.

12. Stroll Through the Commonwealth Avenue Mall

After enjoying a picnic at the Charles River Esplanade, I recommend walking off dinner along the Commonwealth Avenue Mall. You can walk this historical avenue surrounded by trees and 32 acres of green space.

From December 1st to April 1st, the mall is illuminated at night with lights, making it an enjoyable night walk. 

13. Treat Yourself to a Dessert in Back Bay

To finish your day in Back Bay, you can treat yourself to dessert. Believe me. You will deserve it after a full day of walking. There is no shame in eating dessert alone in Boston.

Levain Bakery is known for selling New York’s Most Famous Cookie, but I craved the “crispy-on-the-outside, gooey-on-the-inside” cookies in Boston. Luckily, Levain Bakery has a location in Back Bay.

Besides cookies, Back Bay has plenty of other dessert options. There are many things to do alone in Boston, but getting dessert in Back Bay might just be the sweetest.

14. Start Day 3 at Boston Common

HI Boston is only a 5-minute walk from the Boston Common, which is considered the oldest public park in the United States. It has been the epicenter of American history and is where the Freedom Trail begins.

The Freedom Trail is a 2.5-mile route that connects 16 historic sites. Walking the Freedom Trail is one of the most popular things to do in Boston. Near the Boston Commons, you can also walk the Black Heritage Trail. I recommend walking both trails.

15. Walk the 1.6 Miles Self-Guided Black Heritage Trail

The Black Heritage Trail is a 1.6-mile self-guided trail. You can download the National Park Service App to access a free audio guide. Listening to this guide is a great way to learn more about the thriving Black community that lived in Beacon Hill. 

The App provides audio tracks for each site and a map indicating the historic buildings along the trail, just like it does for the Freedom Trail. 

You can start the trail at the Robert Gould Shaw and Massachusetts 54th Regiment Memorial, across from the Massachusetts State House. 

Noah’s Take: It was highly insightful to tour over a dozen historical sites that told the often-overlooked stories of Black Americans. Most sites are private residences, but you can go inside the Abiel Smith School and the African Meeting House. 

16. Start the Iconic Freedom Trail at the Edge of Boston Commons and the State House

After finishing the Black Heritage Trail, I retraced my steps to the State House to begin the Freedom Trail. The Black Heritage Trail ends less than .5 miles from the State House.

Perhaps the most famous attraction in Boston, the Freedom Trail, is a 2.5-mile, red-brick trail through Boston’s historic neighborhoods that tells the story of the American Revolution. 

Can You Walk the Freedom Trail in Boston by Yourself?

Walking the Freedom Trail is an enjoyable activity to do alone. You can download a free audio guide from the National Park Service to access audio tracks for 22 historic sites.

With the audio guide, you can take a self-guided tour, exploring many different neighborhoods in Boston, including Downtown, North End, and Charlestown.

The NPS says you can spend an entire weekend along the Freedom Trail. So, the beauty of the Freedom Trail is that it can be extended or shortened. It took me about six hours to walk the entire trail, with stops along most sites. 

Sites to not miss during your self-guided tour: Granary Burying Ground, Old South Meeting House, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution, and the Bunker Hill Monument.

17. Visit the Historic Faneuil Hall on Your Boston Solo Trip

One stop along the Freedom Trail that you must take advantage of is Faneuil Hall. The Hall sits as the epicenter of the Freedom Trail, surrounded by Quincy Market and all its fanfare. It was the home of America’s first Town Meeting.

Noah’s Take: If you do not have time to do the entire Freedom Trail, stop by Faneuil Hall. You will find plenty of activities here to do alone and see a lively part of Boston. 

18. Eat From Local Vendors at Quincy Market

A great thing to do alone in Boston is to get food at Quincy Market. This market is a bustling shopping area in the Historic Downtown. From brand shopping to street performers, there is plenty to do and see here during your solo trip to Boston.

It is the perfect place to grab a lobster roll as you take a break from walking the Freedom Trail. However, it can get very crowded.

19. Go Inside the Old North Church That “Started” the Midnight Ride

Along the Freedom Trail is the historic Old North Church. You can go inside this church for $5. The church is open from Monday through Saturday from 10 a.m. – 5 p.m. and Sunday from 12:30 – 5 p.m. According to oldnorth.com, the church welcomes over 500,000 visitors a year.

The Old North Church is famous for signaling to Paul Revere that the British were coming. Three Boston Patriots hung two lanterns in the church’s steeple as the British marched to Lexington and Concord. 

20. Watch Dogs Play at the Paul Revere Park

As you walk the Freedom Trail towards Charlestown, you can visit Paul Revere Park. This park is a very relaxing thing to do alone in Boston. Here, you will find dogs running and people flying kites.

It is a picturesque place to rest while walking the freedom trail. Solo trips are only complete with a nice relaxing trip to a park. 

21. Visit Charleston and the Bunker Hill Monument 

At the end of the Freedom Trail is the Bunker Hill Monument. Although this monument is super impressive to just admire, you should visit the monument from Wednesday to Sunday (10 a.m. to 5:30 p.m.).

During these hours, you can climb up 294 steps to the top of the monument, which is an unforgettable thing to do alone in Boston.

The Bunker Hill Monument honors the Battle of Bunker Hill, where Colonial forces showed they could fight effectively against the British. This battle is considered a turning point in the war.

22. Visit the Charlestown Navy Yard Visitors Center

Next, during your solo trip to Boston, you should visit the Navy Yard Visitors Center. This free museum is open Wednesday through Sunday from 10 a.m. to 1 p.m. and 2 to 5 p.m.

Noah’s Take: The Visitors Center has a few interesting exhibits and artifacts, but the most interesting part of the Navy Yard is visiting the two ships that sit past the Visitors Center.

23. Visit the Below Deck of an Active Navy Ship: The USS Constitution 

One of the final stops on the Freedom Trail is The USS Constitution, the oldest commissioned warship afloat. After a security check (make sure to have a form of identity ready to be checked), you can go aboard the ship for free. YES, for free. 

There is also a USS Constitution Museum that operates on a suggested admission of $10. The museum is open daily from 9:30 a.m. to 5 p.m., while the ship is open Tuesday through Sunday from 10 a.m. to 6 p.m.

Noah’s Take: I enjoyed going below deck and seeing the ship’s inner workings. It was a bit cramped, and you had to climb a few ladders. But it was totally worth it. 

24. Take a Self-Guided Tour Through the Restored WWII Cassin Young

Alongside the USS Constitution is the WWII Cassin Young. This ship was involved in seven Pacific battles in World War II. 

You can take a self-guided tour and walk along the ship deck… for FREE. I thoroughly enjoyed this tour as well.  

25. Take a Ferry Back to the City Center

After touring the Cassin Young, walk 10 minutes to the Charlestown Navy Yard Ferry Terminal and take the Charlestown Ferry to Long Wharf. The trip will cost about $3.70 in cash, and it is worth every penny. 

Noah’s Take: Taking the Charlestown Ferry is the perfect, most picturesque way to travel back to Boston’s city center after finishing the trail. It seriously is one of my favorite things to do alone in Boston. No need to walk two more miles or take the subway and miss out on epic views. 

Once you complete the Freedom Trail, reward yourself with a beautiful ride across the bay. It will be a highlight of your solo trip to Boston.

26. Watch the Sunset at Christopher Columbus Park

The ferry will drop you off right in front of Christopher Columbus Park. It is a nice park to people-watch, and if you plan it properly, it can be a calming place to enjoy the sunset. 

There are plenty of cute picture opportunities in this area as well. 

27. Support Local Vendors at Boston Public Market

One of my final stops in Boston was at Boston’s Public Market. This is no ordinary market. It is a non-profit organization that supports local entrepreneurs. 

There is something for every appetite here. You can find locally sourced New England Food, from fresh foods to prepared meals. This market is a great place to eat on your solo trip to Boston.

28. Take Self-Timers to Close out Your Boston Solo Trip

To end your enlightening and exhausting solo trip in Boston, take some selfies in the street to document the experience.

Noah’s take: As I walked back to Boston South Station to take an Amtrak train home, I found a few posts along the street where I could prop my camera up and snag a shot.

It was the perfect way to close out an excellent solo trip. Of course, no trip will or can be perfect, but Boston is a fantastic city for rewarding solo travel. There are so many things to do alone in Boston, from historical tours to upscale shopping; you will fall in love with Boston!

How much money did I spend on a 3-day Boston Solo Trip?

I spent about $170 on during my solo trip to Boston. I saved considerably by opting for supermarket food over dining out each meal. Essentially, all the activities I did in the city were free, besides going inside the Old North Church. 

• Hostel: $80

• Food: $55

• Shopping: $30

• Attractions: $5

• Transportation: $10

Visiting the East Coast? Read all of my East Coast guides:

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