stone house, Nathaniel Austin, Charlestown ma

What do you know about Charlestown, one of Boston’s many neighborhoods? Take a virtual tour with me, and learn just enough to be dangerous!

Some Basic Charlestown History

The oldest neighborhood in Boston, Charlestown was originally a separate town laid out by engineer Thomas Graves in 1629 to ready it for settlers coming from England. Named for Charles I of England, it was also the first capital of the Massachusetts Bay Colony.

Charlestown is located on a peninsula just north of the Charles River and across from downtown Boston. The land was once called Mishawum by the Massachusett, the indigenous people whose population was decimated by diseases transmitted by the English settlers.

Fast forward to 1775 when Charlestown was the site of The Battle of Bunker Hill, the bulk of which actually took place on Breed’s Hill nearby. Most of the town was destroyed by the British, and it wasn’t until 1786 that rebuilding began in earnest and a bridge was built between Charlestown and Boston. The Navy Yard was established in 1800, and Charlestown State Prison opened in 1805 (the site of modern-day Bunker Hill Community College).

Charlestown ma, federal architecture
A simple but charming federal style house in Charlestown, MA with glistening twelve-over-twelve windows.

In the 1860s waves of Irish immigrants began arriving, and Charlestown soon became an Irish Catholic stronghold. Thousands of residents joined the ranks of the Union Army and Navy during the Civil War, and the Navy Yard was responsible for building many ships important to the conflict. In 1874, Charlestown was annexed to Boston and became one of its many neighborhoods.

Important Charlestown Landmarks

  • The most well-known landmark in Charlestown is the Bunker Hill Monument, constructed from 1825-1843 appropriately on Breed’s Hill to commemorate the Battle of Bunker Hill. The 221-foot granite obelisk was one of the first monuments of our new country, and it was made of Quincy granite transported to Charlestown via the Granite Railway, expressly built for that purpose. Climb the 294 steps of the monument for an incredible view, and visit the Bunker Hill Museum across the street to learn more. Admission is free!
  • Down by the waterfront is the Charlestown Navy Yard, home of “Old Ironsides” the USS Constitution (the oldest commissioned ship in the US Navy), the USS Cassin Young (a destroyer built in 1943), and the USS Constitution Museum. One of six original Navy Yards established to support the US Navy, the yard is now a historic site. Admission is free, and visitors can board both ships. A touching Korean War Memorial is at the Navy Yard as well.

  • The Warren Tavern is also a historic site, but one where you can enjoy a pint with friends while you soak in the atmosphere of a 1780 bar. The oldest tavern in Massachusetts and one of the first buildings erected after The Battle of Bunker Hill, it was a frequent haunt of Paul Revere and at least one visit by George Washington is documented. The tavern is named for Doctor John Warren, a physician and general who played an important role in the American Revolution. He died during the Battle of Bunker Hill and is also commemorated at the Bunker Hill Monument with a statue.

Charlestown Trivia

I love learning bits of trivia about a place, so here are a few things to impress your friends:

  • Charles Ponzi, for whom the Ponzi scheme is named, was an Italian swindler who moved to North America and was imprisoned at Charlestown State Prison for 14 years when his elaborate scheme of paying off early investors with funds received from newer investors unraveled.
  • A number of movies have been filmed in the neighborhood, including The Town with Ben Affleck (2010) and portions of Good Will Hunting (1997) with Matt Damon and Robin Williams, who portrayed a psychology professor at Bunker Hill Community College.
  • John Harvard, the English benefactor and namesake of Harvard University, lived and died in Charlestown.
  • Paul Revere’s midnight ride began in Charlestown after he borrowed a horse from fellow patriot John Larkin (who borrowed it from his father, Samuel Larkin).
  • From the 1960s-1990s, Charlestown was infamous for its Irish Mob presence, with the Charlestown Mob headed by the McLaughlin Brothers. They were heavily involved in the Irish Mob War, battling the Winter Hill Gang in neighboring Somerville, and ultimately being eradicated by them.
Charlestown ma, federal architecture
A Federal house in Charlestown updated with black window muntins.

Charlestown Today

Today Charlestown is a desirable neighborhood for young professionals, families, and others who want to live close to downtown Boston for real estate prices that are relatively affordable (for Boston). Its “Townie” reputation has changed dramatically over the last few decades through the process of gentrification, though less so than other parts of the city.

Charlestown’s character is maintained with protections over much of its architecture, and charming gaslights that line the sidewalks in certain areas. Most of Charlestown is residential, but old-school bars now have some competition with newer eateries such as Monument Restaurant or Brewer’s Fork. Retail is somewhat scarce, but a must visit is Place & Gather for gifts and home decor, as well as Junebug for florals.

stone house, Nathaniel Austin, Charlestown ma
A charming Charlestown house built from Outer Brewster Island stone by Nathaniel Austin in 1799.

Come spend a day in Charlestown, enjoying the historic sites, the charming architecture, a delicious meal, and maybe a little shopping. Boston’s North End is just a quick walk over the Charlestown Bridge if you are craving cannoli for an afternoon snack!


As an Amazon Associate I earn from qualifying purchases.

[x_author title=”About the Author”]

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.