The Perfect Introduction to Charlestown

The Perfect Introduction to Charlestown

  • The Charles King Group
  • 08/24/21

I drove in from the South Shore, flying through the tunnel while people pass me, headlights on or headlights off, risking their lives at breakneck speeds regardless - any chance to drive through Boston without traffic feels like an invitation to go a little wild - exiting at the old 23, which is now some ungodly number like 7 or 420 that will inevitably take years to re-remember. Right out of the tunnel, to an immediate left, and follow to the intersection of N Washington and Causeway, the gateway to the outbound bridge. Less than five minutes out of the tunnel and in the city hustle before I turn on to Warren Street and all time seemed to stop. Charm oozes out of the bricks and the colored clapboard and eases any anxiety that I may have been feeling. Here, in the historical neighborhood on a hill, you are transported away from the frenzy of Boston. 

As I waited in the park for a colleague, I mused at the couple across the way, cozied up aside one another even in the heat. A call came out from behind them - a neighbor opening her windows from a weekend away in New Hampshire, asking after the love birds and their plans for the week ahead. From the orange-sided house with the American Flag, a common beacon in this neighborhood for sure, came the neighbor with her pups and proceeded to chat with her counterparts about neighborhood, friends, and family. My walk-about began there at the Training Field and up to Breed’s Hill and the famed monument to The Battle of Bunker Hill. Perched up top at the base of the obelisk you can look down Monument Ave, a well known scene out of the movies, off to the city skyline not too far away. The view I preferred the most though was around the other side of the monument, at the corners of Tremont St and Lexington St, where the brick-red facades part to reveal a lofty stretch of the Tobin Bridge. Off in that direction, as the crow flies, is the much loved Brewers Fork Restaurant along with its sister Dovetail. Walking along the Charlestown Navy Yard, I caught the masts of the USS Constitution which recently set sail in Boston Harbor to commemorate the 209th anniversary of the Ship’s victory and to honor Vietnam War veterans. Headed on up to the Blackmoor Bar & Kitchen for a brew overlooking the marina and a chat with my pal about the silver-lining of #PatioLife. Cross at the busy Chelsea Street to City Square Park to admire a fountain so lovely I could just swim in it. Quick loop around Harvard Street up to Main and its Warren Tavern, a watering hole frequented by our very own Paul Revere. I love a good tavern but if your taste leans more towards bistro, then over to Figs by Todd English. Charlestown has it’s very own Starbucks now too, but Zume’s Coffee House is a must. And no one would dare forget brunch at Monument Restaurant. Most of the shops are clustered along Main Street too… Monroe Home & Style, Junebug florist, Mockingbird Baby & Kids, Bunker Hill Barber Shop… all across from the shopping plaza that houses Whole Foods, CVS, Dunkin, Ace Hardware, and the Post Office… it’s all in walking distance. 

The one thing I was regretting as I walked along the streets was that I was doing it in 80 degree weather. I think I’ll just have to find myself back there in the fall when, I’m told, the Halloween season is fresh in the hearts of the locals. I imagine Ichabod Craine, headless horsemen, and revolutionaries showing up to party in this town, rivaling Salem in its spirit of spook. Aside for some ghostly visitors, the community is alive in Charlestown and caters local activities to families that live there. It seems a great place to raise children, where you can walk down the street and waive to three or more people you know from pre-school or the park (as occurred for my walking companion). But I hesitate to write Charlestown off as a sleepy bedroom neighborhood for families. While, yes, it is that, it is also notable to mention that it is a stones throw away from downtown, Cambridge, Somerville, Assembly Row, the North End, and, ahem, the entirety of Boston Harbors offerings. You’ve got the Orange Line and a ferry to downtown from the Navy Yard. And while there aren’t a ton of options for restaurants and shops, the ones you have are quality! Truly, you get the best of both worlds here in Charlestown. 

Off back to the South Shore - with a quick cross of the street, I was right back on 93S - easier than I ever thought possible Boston! I am excited to visit Charlestown again and explore the neighborhood (read: food) more. Whether you’re looking to relocate, invest, or just need a good day-trip, Charlestown makes the list for stress-free, historic, GORGEOUS, yummy, and accessible.


Work With Us

Charles King Group has been helping local buyers and sellers just like yourself, locate the finest properties and negotiate the best deals. The team takes great pride in knowing the latest market conditions, government regulations, and upcoming developments — so that you don't have to.