Historic Charlestown

Walk in Boston # 5, the historic Charlestown, is a 2.5 to 3.5 miles self-guided tour to visit the oldest neighborhood of Boston and two Historical National Parks.

You’ll also discover the oldest tavern of the state; you’ll have views of Boston West End and North End; you’ll walk in small streets lined by gaslights and rows of brick houses; you’ll be able to take a ferry back to Downtown Boston.

Count from 90 minutes to 3h of walking time, depending on what you decide to do along the trail.

Highlights: the Zakim bridge, the Charlestown bridge, Tudor wharf, Crowley Square, Warren tavern, Bunker Hill, USS Constitution, Boston National Historical parks, USS Cassim, Freedom trail, the Spaulding Hospital.

T-stops: North Station, green and orange lines (start) and Aquarium, blue line (end, if you take the ferry).

Car: never a good idea in Boston but if you insist, Charlestown has a two hours limit on parking spaces open to the public. They are difficult to find during the week, and you have to make sure you don’t stop in a resident only spot. Otherwise, use a parking app to find a place in one of the parkings along the wharf (points G or H). Then, once on the walk, make a loop by joining points G to C, and forgetting points A, B, and J (the ferry).

Good to know: there are restrooms and benches at the two National Historical Parks and on the ferry. There are also benches along the Harborwalk. To eat, you’ll find restaurants and pubs here and there along your way.



A: Your trek starts at North Station, like Walk in Boston # 1, the forgotten West End; this time, however, go on the left once out of the railway station. If you took the T., go out on Beverly St, take it toward Causeway St., and cross it.

You’ll reach Portal Square and from above, you’ll see the traffic emerging from, or entering, the O’Neill tunnel. For once, you are not in it, so enjoy the view!

After the park, turn left on Beverly St. to reach the Harborwalk on your right. The Boston Police Harbor Station is in front of you; on your right, the headquarters of a famous and local brand of sneakers. Go and have a look at its entrance interestingly decorated.

B: You cannot access the stair to the Charlestown bridge due to construction work, so keep left and walk along the police station. You’ll reach a pedestrian walkway going over some locks. They are the ones allowing boats to go from the Charles river to the harbor; they also prevent seawater to go from the harbor to the river. After them, you’ll see a musical sculpture by Paul Matisse, Henry Matisse grandson. Have fun with it!

NB: When the bridge is again open from the wharf, you’ll have the option to take it on its left and see the locks from above. Then you’ll have to take a stairway to your left at the end of the bridge. It will connect you to point C.

In both cases, you’ll have a close view of the Zakim bridge, one of the new landmarks of Boston..

C: Next, turn right to go under the Charlestown Bridge and reach the Tudor wharf.

If this walkway is also closed due to construction, go a bit further, then turn right twice to meet the Harborwalk at the Tudor wharf. Or go directly to point D.

Tudor was the “Ice King” of Boston at the beginning of the 19th century. He was harvesting ice in New England ponds and shipping it all over the world. It is said that no dinner in London was proper without pure clear ice from Wenham lake; Frederic Tudor was the one providing it, and finally making a fortune. That’s what a panel there tells you.

There are also many yachts and sailboats anchored at this point, many used as floating houses. In winter, they are covered with plastic to keep the heat inside.

To have good views of Boston skyscrapers, especially at night, follow the Harborwalk a little bit until the Constitution marina. Then retrace your steps once you’ve had enough with the view. Find a stair allowing you to go under the arch of a building facing the Marriot Residence.

D: From there, cross Chelsea Street and go and see the weather vane on Crowley Square; then some remnants of Native Americans dwellings preciously preserved in the grass.

Next, take the stair in front of you and climb in a small park. At its end, on top, turn right and go down.

E: You’ll soon see Warren Tavern in front of you, at the corner of Main and Pleasant St. It’s the oldest tavern in Massachusetts, yet a lively one.

Built in 1780, it hosted Paul Revere and George Washington. If you want to eat before climbing Pleasant St., that’s a good place to stop.

You are now in the heart of old Charlestown, with gaslight and tree lined narrow streets. You’ll surely find that Pleasant St. is well-named with its rows of colorful houses.

F: Once you reach Bunker Hill Park, you’ll see a 221 foot obelisk; it commemorates the 1st major battle between British and Patriot forces during the American Revolution war. It’s not on Bunker Hill, though, but on Breed’s Hill, where most of the battle took place!

If you plan to go on top of it, and it looks like there are already many tourists around, turn right on High St. You’ll soon be at the Bunker Hill Museum; there, get a free ticket for the climb; it will tell you when you can present yourself at the gate.

You’ll have to decide if you really want to do the ascension, though: there are 294 steps; halfway through them, your muscles calves will tell you that these steps have an unusual high; it will only get worse as you keep climbing; there’s even a good chance it will still hurt the next day. Besides, you won’t be able to see much at the top: the inside platform is very crammed (hence the necessity to control the flow of people in the tower), with only four small windows. Yet you’ll see far in the distance, and you came a long way to reach the Monument; will you renounce so close to the goal?

You’ll have to answer the same question once you reach the USS Constitution downhill.

Before going there, rest on the benches or lawns of the park, surrounded by red bricks colonial houses and a lot of history. There are many panels explaining what happened on this hill.

G: Once rested, go back to High St.; follow the Freedom Trail again toward Winthrop St.; then Adams St. and Chestnut St.. You’ll pass Winthrop Square on your way, a pretty little square in the middle of quiet and residential streets; it could remind you of Beacon Hill if you’ve already been there.

Once at Chelsea St., cross it to access another site of the Boston National Historical Park, the Navy Yard. It’s home to the USS Constitution, a wooden hull, three masts frigate built at the end of the 18th century; it’s the oldest floating naval vessel in the world. You’ll also see the USS Cassim Young, a destroyer from the WW2 era.

Both are free to visit, but the lines can be long; you’ll also be surrounded by scores of tourists once you set foot on deck, so make up your mind.

If you decide to skip the visit, go and have a look at the free museum; you’ll learn everything about the construction of the frigate, its different travels, its nickname (“Old Ironside”), and life on board.

H: You now have two solutions. Follow the Freedom Trail back to the Charlestown Bridge, then North Station; or go a little further north to take a ferry (it’s what the map tells you to do).

In that case, you’ll again have two solutions: take directly the ferry; or keep walking along the Harborwalk to add a 1 mile loop to your trek. You’ll follow the wharfs; have nice views toward Boston; reach Spaulding Hospital and its wonderful playground in front of the sea; then you’ll come back in between old Navy Yard buildings. They are now apartments, offices and hotels but they kept their original character.

Then you’ll be able to take the ferry. It will cost you a few dollars for a 10 mn ride to the Aquarium. The boats run every 30 minutes (but verify before).

Once at the Aquarium, if you want to walk more, you will be able to branch out to the Walk in Boston # 14, touristic Waterfront, point D.

Otherwise, if you came back through the Charlestown Bridge, you’ll find the Walk in Boston # 1, the forgotten West End once at North Station; Walk in Boston # 2, the other North End, will also be there if you are ready to follow it in reverse.

Now, to know more about the historic Charlestown and see many image of the city throughout the years, you can consult Charleston, MA, Images of America.

And before you go, don’t forget your guide, and see how to thank him at the bottom of the page. Then enjoy the rest of your day!


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