A Complete Guide to Boston’s Freedom Trail

Boston’s Freedom Trail is the red brick (or painted) line on the ground that connects 16 sites that are significant to the city’s Revolutionary history. With 2.5 miles of history, seeing it all in one day may seem overwhelming.

Although I live near the city (and I used to work on the Freedom Trail shhh…) I’ve never done the whole trail in one day until recently. And let me tell you, hitting all 16 stops in one day is exhausting. But it’s totally doable, and if you’re a history nerd like me you’ll definitely love doing it! Ready to go for a walk?

How to see the trail

You can take a guided tour of the trail, whether it be a free tour through the National Park Service or a paid one from any number of companies who host tours along the trail. A guided tour can be a great way to get some of the information for the sites on the trail in a more engaging way, but the tours do not cover the entire trail, and they do not get you into the sites that charge admission.

Another alternative that you sometimes hear people suggest is to take a trolley tour. A trolley is a fun way to see Boston in general but there are certain areas of the trail where the streets are too narrow to fit trolleys, so you would miss out on these spots (like the North End, which includes the Old North Church and the Paul Revere House).

To see the entire trail in one day, I would recommend taking a self-guided tour. You can pick up self-guided brochures from a visitor center or download a variety of mobile apps to help give you information while you’re walking the trail yourself. Although some of the sites (notably the ones that are now museums) have lots of information readily available, others (like Old City Hall and the site of the first public school) do not really have lots of information outside.

Where to start

You can technically start wherever you want (lots of people even walk the trail ‘backwards’) but if you want to do it all in one day I would start at Boston Common. The official start of the trail is right in front of the visitor center on Boston Common– if you’re there too early for tours to be starting it may be easy to miss but it’s the green kiosk located at 139 Tremont Street.

You’ll also want to start early. We started at Boston Common at 10:00 am, and by the time we reached the end of the trail in Charlestown we had just barely missed the museum at the Bunker Hill Monument (and the interior of the monument itself) since they closed at 5:00 pm. We’ve done both before, so it wasn’t a big deal, but if we had started at 9:00 am instead of 10:00 am I think we would have made it just fine with the extra hour.

The Common is the oldest public park in the country (est. 1634). There is lots to see on the Common aside from what the trail covers, so if you have the time it’s worth walking through (you can ice skate on the Frog Pond in the winter and walk over to the Public Garden and ride the Swan Boats in the summer). In terms of Revolutionary history the Common was used for public celebrations where colonists celebrated victories like the repeal of the Stamp Act, and it’s where the Redcoats who made their way to Lexington and Concord made their camp before leaving the city.

Sites along the trail

From the Common the trail will bring you up towards the Massachusetts State House. (Note: This is the current state house in Massachusetts, another stop on the trail is the Old State House and these are entirely different sites). The State House is open for (free) tours during the week, so if you happen to be in town Monday-Friday catching a tour isn’t a bad idea. While not a site on the Freedom Trail directly across the street from the State House is the Robert Gould Shaw and the 54th Regiment Memorial which honors some of the first African Americans who fought in the Civil War.

The next stop on the trail is the Park Street Church, which was built in 1809 when it was used as a granary (meaning it stored the town’s grain). As its name suggests, it is still a functioning church so the visiting hours vary based on the time of year and when church services are going on. You can typically visit from the Freedom Trail between 9:30 am and 3:00 pm in the summer months.

Follow the trail from there and you’ll come to the Granary Burying Ground, which is home to lots of famous graves like Paul Revere, John Hancock, Samuel Adams, the victims of the Boston Massacre, and ‘Mother Goose.’ You’ll see a large marker for “Franklin” in the middle the burying ground, but this is actually for Ben Franklin’s parents– Ben is buried in Philadelphia.

Kings Chapel is next, and this site was used by Boston’s (small) Anglican community in the 18th century. You can take a tour of Kings Chapel (for free) daily unless there is a service or other special event going on as this one is also still a functioning church.

Right next door is the Kings Chapel Burying Ground which is also home to some famous graves like John Winthrop (Massachusetts’ first governor), and Mary Chilton (the first woman to disembark the Mayflower). Right in the front of the burying ground is Joseph Tappings grave which features one of the most well-known stone designs of a skeleton fighting with Father Time.

The next stop on the trail is the Ben Franklin Statue and the Boston Latin School. This stop is a bit misleading depending on which guide you’re looking at as the school is no longer still standing at this site (in fact, Old City Hall was built on the foundation of what was once the school). In lieu of a physical school building, continue following the trail and you’ll come to a marker on the sidewalk showing where the school was. The Ben Franklin statue is located directly behind this in the courtyard of Old City Hall.

Continuing down School Street you’ll come to the site of the Old Corner Bookstore, which is Boston’s oldest commercial building (est. 1718). During its time as a bookstore it was a common gathering place for writers like Nathaniel Hawthorne and Henry Wadsworth Longfellow. It’s served a number of different purposes over the years, and you may not recognize the building at first because its current tenant is Chipotle. Still, stop and read the plaques on the outside of the building or use the augmented reality app (found on the signage outside) to get a glimpse of the building’s past.

Across the Street is the Old South Meeting House (est. 1729) which is known for being the site of the tea tax debates that led to the Boston Tea Party. Inside you can view the meeting house itself along with an exhibit that covers its history. This is the first site on the trail that charges admission ($6 for adults). If you are also going to the Paul Revere House, you can purchase a combo ticket called the Patriot Pass at the Old South Meeting House for these two sites.

When you do visit the Old South Meeting House (and the other museums that charge admission) be sure to take your time looking at everything. Each of these sites are historic buildings in addition to museums with exhibits, and you’ll really get more out of your visit by spending some time reading everything inside (or by taking the tour at the Old State House).

After leaving the Old South Meeting House continue along the Freedom Trail down Washington Street and you’ll come to the Old State House. Much like the current state house today. the Old State House was where the colonial government was housed. Inside the Old State House you can take a tour or explore the exhibits on your own ($10 admission). As you continue along the trail leaving the Old State House you’ll see a circle marker on the ground which signifies that the Boston Massacre took place right here.

If you’re like us, this is probably around the area of the trail where you’ll start to get hungry. There are plenty of restaurants coming up at and around Faneuil Hall, which is the next stop on the trail. If you want to save time and have something quick you can walk through Quincy Market will you’ll find all different kinds of quick service food with everything from clam chowder to Indian cuisine. For a table service meal, continue walking along the Freedom Trail past Faneuil Hall.

In terms of the Freedom Trail, Faneuil Hall is where many town meetings were held leading up to the Revolution. The tea tax debates before the Boston Tea Party for instance were held at Faneuil Hall before they were moved to the Old South Meeting House to better accommodate the crowds. Inside Fanueil Hall you’ll find exhibits and information hosted by the National Park Service, and rangers also give historical talks here regularly throughout the day. (The National Park Service Visitor Center is typically located inside Faneuil Hall, however during spring 2018 it is temporarily located next to the Old State House while preservation work is done on its permanent location). 

If you opted for a more sit-down lunch, pass Faneuil Hall staying on the Freedom Trail until you come to Union Street. Here you’ll find pubs and taverns some of which are actually related to the history you’re learning about on the Freedom Trail. The Green Dragon for instance was often used as headquarters for the Sons of Liberty, and the Union Oyster House is the oldest continually functioning restaurant in the country (since 1826).

During this walk on the Freedom Trail we decided to try the Union Oyster House since we’ve never been. Our meals were good and it’s a nice place to sit and relax with some classic New England food since it is right on the trail, but I will say that it is very touristy. I don’t mean to sound surprised by that because I’m not obviously, but the decor, the menu, the prices, (the gift shop!)–everything about it is very touristy. And this isn’t necessarily a bad thing, it was just kind of weird for us because we live here. If you’re looking for that kind of touristy experience which you very well may be, you’ll probably really enjoy this atmosphere!

If you want to eat somewhere still related to the history on the Freedom Trail but with less of an obvious tourist-factor, I actually prefer the meals I’ve had at the Green Dragon. And this restaurant can still give you that added bit of history without being too in your face about it. They’re both really great though–just a personal preference to consider!

From Union Street, the Freedom Trail turns into Boston’s North End. If you have time to stop for coffee or a cannoli this is the place to do it! The next stop on the trail which is located in the North End is the Paul Revere House. If you purchase the Patriot Pass at the Old South Meeting House you’ll be all set with admission by the time you reach the Paul Revere House, if not admission is $5 for adults.

After we went through the admissions area for the Paul Revere House, we stumbled upon Paul Revere himself! He showed us how he makes spoons and other items as a silversmith, and he also told us about his famous ride. If you happen to see any reenactors or interpreters while walking the Freedom Trail, be sure to stick around for their presentations. We’ve been to the Paul Revere House a couple of times, but this presentation was new to us and it really added to our visit!

Once inside the house, you’ll be able to take a self guided tour of the home and exhibits. As this is self guided like the Old South Meeting House, definitely make sure to take your time reading all of the exhibits. If you rush through with a quick glance at the house you won’t take away as much from the experience. And museum staff are always in the staff to answer any questions too.

Next is the Old North Church, which you may be familiar with as the church where the lanterns were hung to signal how the British soldiers would be arriving and going towards Lexington and Concord (“One if by land, two if by sea…”) Admission to the church is by donation as it is still a functioning church, and it’s typically open to the public when services are not going on. The Old North Church also has education staff on hand who periodically give talks and are also available to answer questions.

After the Old North Church we started to get a little bit tired, and I imagine this is where most people start to feel it. It actually seemed like the trail was more crowded in the morning, and we saw some people who were near us most of the day sort of disperse when they finished visiting the Old North Church. I’m not sure if most people aren’t finishing the whole trail in one day, or if they’re just giving up but I thought that was an interesting observation. Despite starting to feel tired, we kept going because our whole goal was to do the entire trail in one day.

Copp’s Hill Burying Ground is the next stop, and the last stop on the trail before you head over the bridge to Charlestown. Increase and Cotton Mather (known for his Memorable Providences, Related to Witchcraft and Possessions) are both buried here in the Mather family tomb. This cemetery is overlooked in my opinion compared to the other Freedom Trail cemeteries, and with only a handful of names most tourists will recognize (and even then I’m not sure how many people outside of New England would know the Mathers by name) but even so it’s a really interested spot for walking around and reading the epitaphs and taking in the various tombstone designs.

I didn’t manage to snap a photo (it was getting COLD, windy, and rainy that afternoon) but when you leave Copp’s Hill following the Freedom Trail you’ll actually come across the narrowest house in Boston. It’s pretty cute as it’s a little wooden house sandwiched between the other brick buildings, but if you do stop by to see it just please remember to be respectful since it is a private residence.

The walk from the North End to Charlestown is the part of the Freedom Trail that lots of people dread. When I worked on the other end of the Freedom Trail, I used to park in Charlestown and walk essentially the whole trail to/from work each day like it was nothing, but doing this walk after a whole day of touring all of the sites is a whole different story.

If the weather is chilly/cold/rainy/snowy like it was the day we did this walk be sure to wear more layers than we did. We didn’t feel like carrying an umbrella and since it was actually sunny out when we left in the morning we weren’t too worried about freezing–but that’s New England for you!

In season (read: summer) the USS Constitution Museum is typically open an hour later than the ship. Knowing that we were getting close to 5:00 at this point we opted to do the ship first, but if you have more time we would actually suggest doing the museum first. The museum gives you much more background information about the ship (and the War of 1812–not the American Revolution contrary to the ship being on the Freedom Trail) so it can be helpful to have that knowledge as you go onto the ship.

If you’re cutting it close on time like we were there is still plenty of information on the ship. There is a small exhibit before you go aboard (though this largely focuses on the Navy Yard as a whole, not just the USS Constitution) and there are sailors on duty that can help answer any questions and teach you more about the ship’s history. You should have this on you anyway, but if you visit the USS Constitution remember that guests who are 18 and over need a photo ID to board.

The USS Constitution Museum is located right across the lot from the ship in the Navy Yard, and there you’ll find lots of exhibits and interactive activities about the oldest commissioned naval vessel still afloat in the U.S. Depending on how you get around museums you can easily either breeze through in 30 minutes or so or spend well over an hour exploring the museum. Admission is by donation with suggested pricing listed by the entrance area.

By the time we left the USS Constitution Museum it was after 5:00 so the Battle of Bunker Hill Museum and access to the top of the monument were closed. This wasn’t a big deal for us since we’ve been before, but it’s worth noting that because our whole goal was to finish the entire trail in one day. I would still say we did accomplished this goal, since it really isn’t possible to do everything in one day, and we knowingly took a leisurely lunch because we’ve done all of the sites before– we definitely could have had a quicker lunch and made it to the top of the monument if we thought to do that.

Some of the sites have special programming and guided tours in addition to the self-guided exhibits, and doing every single thing on the trail in this respect would probably take you two full days. If you really want to get the whole trail done in one day I’d recommend eating on the go rather than at a table service restaurant. If you don’t need the visitor center to start, you could also save some time by starting the trail up at the state house instead of at the visitor information booth on the Common.

Some things to keep in mind

  • A lot of the hours for the sites on the Freedom Trail vary by season, some of the most popular sites have hours you may not expect (like the State House only offering tours during the week and the USS Constitution being closed on Mondays and Tuesdays). It’s also worth noting that while buildings that are still active churches welcome the public, you can’t get in to explore as a tourist while there are services going on.
  • You can walk the trail year-round if you’re comfortable with being out in the weather, and most sites will be open but the hours do vary a bit. The majority of the sites are open year-round, but some have shorter hours in the winter so you may have to be more strategic to fit it all into one day, or split the trail over two days if you want to do everything.
  • Walking the trail itself is free but select sites do charge admission and others are by donation. It doesn’t hurt to look up the prices ahead of time so you can be prepared for where/when you’ll need to pay. And remember to ask about student or military discounts if either of those apply to you.
  • If you happen upon a site that has public restrooms– use them! Not every site has public restrooms and if you don’t use them when you can you may find yourself paying to buy a coffee somewhere down the trail so you have access to a restroom.

Have you walked Freedom Trail before? Although I’ve walked the trail more times than I can count, doing the entire thing in one day was a whole different experience– it was exhausting, but we really enjoyed it! Let me know in the comments if you’ve done the Freedom Trail before, or if you have any questions for when you do during a trip to Boston!

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