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Discover Charlestown, the Oldest Neighborhood of Boston

Dominique is the author of Boston Citywalks & New York Citywalks, two sites with 18 self-guided tours to visit Boston or New York on foot.

A taste of Charlestown

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The beginning

If you're like me, you can spend years next to an interesting place without ever going to see it, but telling yourself, I might have to stop one day.

In the case of Charlestown, Boston's oldest neighborhood, it lasted for about 20 years.

In my defense, I must say that Boston is a very pleasant destination to visit and that the rare times when I could go there, I chose the center.

Like any newcomer, I had followed the Freedom Trail to familiarize myself with part of the city but in front of the Charlestown Bridge, I had stopped, too tired to cross it and to see what was on the other side.

Big mistake!

Charlestown is Beacon Hill, the most chic and expensive neighborhood of the city, but in the countryside. By that I mean it's a quiet and neat neighborhood with small sloping streets amid colonial-style townhouses with flags fluttering in the wind and gas-fired street lights to accentuate the retro charm of the place.

That hasn't always been the case, though. Until 1974, Charlestown was also the site of the largest shipyard in the United States, founded in 1800 and the remains of which are now a National Historic Park.

During the Second World War, the site had 52,000 workers who lived in the surrounding area. Charlestown was also the arrival of the Middlesex Canal and its riches from the West. Finally, it welcomed the flotillas of steamboats arriving from Europe with their immigrants. The ideal place for the emergence of gangs in the 19th century, and the creation of the very specific identity of the Townies who recognized each other thanks to their insignia in the shape of a four-leaf clover.

Since the 1990s, though, they have been replaced, at least in the historic part of the town, by a Yuppie and middle-class population attracted by the colonial character of the place.

In this, they bring to life in their own way the beginnings of Charlestown when the city was the capital of the Massachusetts Bay Colony, a group of 1000 Puritans who had more or less kindly expelled the American Indians from the land.

However, what makes Charlestown known and visible from afar is that it is above all the site of the 1775 battle against the English; a battle commemorated by the Bunker Hill obelisk, today also a National Historic Monument.

This means that if you come to Boston and want to visit the town, you can take the Walk in Boston # 5, the Historic Charlestown, and you will have a lot of things to see.

A taste of the USS Constitution

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The itinerary

The walk departs from North Station, across what is still the Charles River before it empties into Boston Bay.

It will end at the ferry that goes from Charlestown to Boston Aquarium, a 10-minute mini cruise that will allow you to take pictures of the buildings of downtown Boston and pass off the North End, the Italian district.

At its beginning, you have the opportunity to cross the Charlestown Bridge, an old iron bridge that overlooks the newer Zachim Bunker Hill Memorial Bridge, and a set of locks that control the water level of the Charles River.

Once you reach the other end of the bridge, you'll see the Tudor's Wharf below on your right, and learn about the astonishing story of the Ice King as it is explained on a panel placed there.

If you are staying in Charlestown, this will be your starting point - you won't be taking the ferry at the end but you will save $ 4.80!

You then pass through charming little streets to reach the Bunker Hill Monument at the top of the hill. This hill is not the one where the battle took place, though, but it was the only one cleared and available to erect the monument when it was decided to build one!

Along your way, you'll see and even be able to enter the oldest tavern in the USA if what the owners say is true. In any case, it is a very pleasant pub and the opportunity for a refreshing stopover.

This will be welcome because if you want to climb the obelisk at the top of the hill, you will need strong legs: its 294 steps are unusually high and will leave you exhausted once you come back down.

Before you try it though, stop by the visitor center around the perimeter of the square. There you will get a timed pass for your climb as the number of people in the obelisk is limited. In addition, on the 3rd floor of this center, you will find models showing you what Boston looked like at the time of the battle. Not to be missed to see how a city is changing. You will also see multiple panels telling you the history of the city and of the battle.

Even if you are tired when you get out of the obelisk, it would be a shame to stop your walk there and take a taxi home: as if you go down the hill, you'll reach the Navy Yard, its museum and its two famous ships, the USS Constitution and the USS Cassim.

All can be visited for free and it will complete the historical part of your walk.

As for the tourist part, find a pier a little further where the ferry lands. Once on the ferry, sit in the air on the upper deck and let it lead you towards the center. It will be the perfect ending to your walk.

Have fun!