The Charlestown trek is a 2.5 to 3.5 miles self-guided tour to visit on foot the oldest neighborhood of Boston, and two Historical National Parks. You’ll discover the oldest tavern of the state; you’ll have views of the West End, the North End, and the West and North suburbs; you’ll walk in small streets lined by gaslights and rows of brick and wood houses; last but not least, you’ll be able to take a ferry back to Downtown Boston. NB: trek updated in April 2019.

Count from 1h30 to 3h of walking time, depending on what you decide to do on 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.

A: Your trek starts at North Station, like the West End trek; this time, however, go on the left once out.

You’ll soon reach Portal Square; 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 brand of sneakers, with an entrance interestingly decorated.

B: For now (April 2019), you cannot take the access stair to the Charlestown bridge, an old and rusty, yet imposing steel bridge. It needed repairs and it’s what going on right now.

Instead, follow the wharf on your left to 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.

You’ll have a close view of the Zakim bridge; a bit further, don’t hesitate to play with the musical sculpture of Paul Matisse, Henry’s grandson.

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

NB: if this walkway is closed, go a bit further, then turn right twice to meet the Harborwalk at the Tudor wharf. Otherwise, you can also 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; 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.

The ferry solution will cost you a few dollars for a 10 mn ride to the Aquarium. They run every 30 minutes (but verify before).

Once at the Aquarium, if you want to walk more, you can now branch out to the Waterfront trek.

If you came back through the Charlestown Bridge, you’ll find the West End trek at North Station; the North End trek if you are ready to follow it in reverse, ends there too.

Good to know: There are restrooms and benches at the two National Historical Park location, 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.

T-stops: North Station (start) and Aquarium (end, if you take the ferry)

Tips for the scout: they are welcome, see suggestions at the bottom of the page. Thanks in advance for your contribution!

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