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The Best Things to Do in Boston’s Charlestown

A street in Charlestown
A street in Charlestown | © Mike Norton / Flickr
Charlestown is a historic, waterfront neighborhood in Boston. While visitors may only come across this district if they walk to the end of the Freedom Trail, there’s so much more to experience. Locals love this part of the city for its chill vibes, while travelers will enjoy the views, the quaintness, and the number of things to do.

Climb the Bunker Hill Monument

You can’t come all the way to Charlestown and not climb the famous Bunker Hill Monument. History buffs will love climbing up the steps of Bunker Hill to the very top of the monument to peer out over the city. The memorial commemorates the Battle of Bunker Hill, the first important battle of the Revolutionary War. Admission is free, and you can climb the tower between 9:30 am and 4:30 pm. After all of that climbing, relax on the well-kept grounds, which are especially beautiful in summer.

Grab a drink on a deck

Locals know that the best views of the city are best taken in with a meal or a drink. Pier 6, which has both a roof deck and a patio area, has panoramic views of Boston’s skyline and harbor. The restaurant is right around the corner from the USS Constitution. Another great dining spot is at the gastropub Brewer’s Fork.

Check out the USS Constitution

The USS Constitution is the oldest commissioned ship in the U.S. Navy. Indeed, Naval officers and crew still board her to serve, as the warship is now operated as a historic site with the National Park Service. Stop by to board the ship and see what life was like on the boat. If you’re interested in learning more, the USS Constitution Museum is close by.

USS Constitution © Alan Kotok / Flickr

See the Navy Yard

If you’re at the USS Constitution, then you’ve already found the Charlestown Navy Yard! The yard dates back to 1800, and it was a working part of the Navy until 1974. It’s now largely a national park including the section encompassing the USS Constitution and its museum. Grab a pastry or sandwich from a nearby coffee shop (such as Zume’s Coffee) and sit down in the Navy Yard to enjoy the superb views of downtown Boston and Eastie.

Rent bikes

Charlestown is a perfect place to bike (though it’s occasionally a little hilly). Bike through the charming streets to explore more of the area. Blue Bikes has locations all around Boston and Charlestown where you can pay as little as $2.50 for a 30-minute ride.

Go window shopping

Few think of Charlestown as a shopping destination, but there are some quaint small businesses along the neighborhood’s streets. Take a stroll down Main St. and pop into boutiques like Mockingbird. Haven Boston and Place & Gather are also nearby.

Charlestown © Kan Wu / Flickr

Take a fitness class

Charlestown is home to families and professionals, so it only makes sense that there are some great fitness studios around. Try out a spin class at Ctowncycle, or take a yoga class at Asana Charlestown. If you aren’t looking to pay for your workouts, you can still go for a heart-pumping run in the park. (Paul Revere Park is another option.)

See the St. Mary – St. Catherine of Siena Catholic Church

Stop in to see the beautiful St. Mary – St. Catherine of Siena Catholic Church, designed in the 1880s by Patrick Keely, who designed many Catholic churches in America during the 19th century. Be sure to admire the hammer-beam oak ceiling.

Visit a museum

There are plenty of museums to choose from in Charlestown. If you’re looking to soak up more Revolutionary War history, check out the Battle of Bunker Hill Museum for a refresher on the facts. The USS Cassin Young is also a fascinating sight to see, as it was a destroyer ship used in WWII.

Go to the Oldest Tavern in Massachusetts

Plenty of bars claim to be the oldest tavern in Boston or New England or America, but Warren Tavern can actually say it. The bar dates back to 1780, and it was one of Paul Revere’s favorites. It is said that George Washington also stopped by. Grab a pint and revel in the history.