A 2 miles, 1:30 to 2 hours trek, mainly outdoor, in the oldest neighborhood of Boston to visit two Historical National Parks and find the oldest tavern of the state before taking a ferry back to Downtown Boston.

You’ll also 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.

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


A: Your trek starts at North Station, like the West End trek, but this time, you’ll go on the left. You’ll soon reach Portal Square where you’ll be able to look from above at the traffic emerging from, or entering, the O’Neill tunnel. For once, you are not in it, so enjoy the view! You can even see some window washers up above if you come at the right time!

After the park, turn left on Beverly Street (it’s better than going straight on, as indicated on  the map) to reach the Harborwalk on your right. Once there, you’ll see on your left the Boston Police harbor station and you’ll perhaps think patrolling the harbor all day long on a speed boat is a good and fun way to earn a living (if you like boats and the sea, of course!)

B: Next, take the access stair to the Charlestown bridge, and go left at the top. It’s your chance to look closely at this old and rusty, yet imposing steel bridge before it disappears when construction of its replacement starts in 2017. On your left, below, take a look at the locks allowing boats to go from the Charles river to the harbor, and preventing seawater to go from the harbor to the river. You also have the closest view of the Zakim bridge you can have without being actually on it (you cannot, anyway!)

C: At the end of the bridge, take a stair on your left to reach the Harborwalk again, but on the Charlestown side. You’ll see many yachts and sailing boats at anchor there, as well as a panel telling you that you stand on Tudor wharf.

Tudor was the “Ice King” of Boston at the beginning of the 19th century, 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, and Frederic Tudor was the one providing it, and making a fortune by doing it.

To have good views of Boston skyscrapers, especially at night, follow the Harborwalk a little bit until the Constitution marina. Then retrace your steps to 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, along with remnants of Native Americans dwellings preciously preserved in the grass. Next, take Main Street, and follow the Freedom Trail for two blocks. When it goes right on Winthrop street, keep going straight for two more blocks.

E: You’ll reach Warren Tavern at the corner of Main and Pleasant Street, the oldest tavern in Massachusetts, yet a lively one. Built in 1780, it hosted Paul Revere and George Washington, and if you need some food and drinks before climbing Pleasant Street, that’s a good place to stop.

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

Once you reach Bunker Hill Park, you’ll see the 221 foot obelisk commemorating 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 Street until you reach the Bunker Hill Museum. You’ll get there a free ticket for the climb, telling you when you can present yourself to the gate.

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

You’ll have to answer the same question once you reach the USS Constitution downhill from where you are, but 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 if you need to know more.

H: Once rested, go back to High Street and follow the Freedom Trail again toward Winthrop Street, then Adams Street and Chestnut Street. You’ll pass Winthrop Square on your way, a pretty little square in the middle of quiet and residential streets that will remind you of Beacon Hill if you’ve already been in this part of Boston.

Once at Chelsea street, 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, and 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, and you’ll 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 museum where you’ll learn everything about the construction of the frigate, its different travels, its nickname (“Old Ironside”), and life on board.

I: It will then be time to go back to Downtown Boston, and you have two solutions. Follow the Freedom Trail back to the Charlestown bridge, or go a little further north, find Baxter Road behind the Museum, and go and take a ferry at the end of this road.

The ferry solution will cost you a few dollars for a 10 mn ride to the Aquarium, and pretty views of the North End and Downtown Boston. Ferries run every 30 minutes.

Once at the aquarium, or at North Station if you took the Freedom Trail, you are at the end of this trek. If you want to walk more, you can now branch out to the Waterfront trek at the Aquarium, or the West End trek at North Station

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.

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

Tips for the guide: they are welcome but as we live in a virtual world, it will be easier to follow the suggestions at the bottom of the page. Thanks in advance!

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