Follow the Red-Brick Road

I’m finally done with my final exams, so that officially means that it’s summer. Time for beach days, sunscreen, and the ever-present threat of heat exhaustion. But for now, let’s go back to the chilly streets of Boston. Within the grimy pavement of the city’s sidewalks lies a thin little line of bright red bricks. It winds its way through skyscrapers, past graveyards, and down cobblestoned lanes, stretching from Boston Common to Bunker Hill, on the North bank of the Charles River.

This is the Freedom Trail, Boston’s red-brick road.


Ben Franklin

Here, the city’s rich history unfolds as quickly or as slowly as you walk, old buildings and statues of the founding fathers popping up out of nowhere, eager to tell you Boston’s story.

Old South Meeting House

I started near the Park Street T stop at the Eastern corner of Boston Common, continuing north along Tremont St. and East on School St. until I could see the Old South Meeting House (the original site of the Boston Tea Party), a small brick, spired, edifice dwarfed by the sleek high-rises of Downtown.

Then I continued Northeast on Washington and Congress Streets to reach what is probably the center of ‘tourist’ Boston: Faneuil Hall. Famous for its indoor markets, Faneuil Hall has been unfortunately overrun by visitors. Don’t expect a hip, local market like San Francisco’s Ferry Building or New York’s Chelsea Market (although they do have a Wagamama, the best pan-Asian restaurant ever).

North End Park
Near Faneuil Hall

After winding through a thin cobblestone street or two near Haymarket, I followed the Freedom Trail across the decidedly modern North End Park (it kind of feels like the High Line in New York) to reach the famous North End. Noted for its multitude of Italian restaurants, the North End is Little Italy on steroids. Once you cross North End Park, all the skyscrapers disappear behind you to make way for a sea of red and orange brick houses, all nudged up snugly against each other.

Though the North End hasn’t been spared from the tourism craze (Hanover Street, the main drag, definitely feels American), it’s still a great place to venture down a minuscule side street to find some quality pasta, pizza, or meatballs. I ate some great pizza at Locale (further up Hanover Street), followed by one of Mike’s Pastry’s famous Cannolis (trust me, they’re fantastic).


Food and history aren’t the only things you’ll find on the Freedom Trail. At the Southern end of Hanover Street, I descended a flight of stairs and ended up at the Improv Asylum, an underground performance space for the city’s funniest nightly activity. The Asylum’s mainstage show contained both improv and rehearsed sketch comedy, all of which made my face hurt from laughing so much.

Paul Revere

The Freedom Trail veers off of Hanover Street and soon finds itself in the Paul Revere Mall, a quiet promenade with trees, fountains, and of course a statue of Revere himself. At the end of the mall lies the Old North Church, from whose bell tower Revere famously sent his “One if by land, two if by sea” signal.

Old North Church

The little brick line ascends a hill in the North End, passing by a cemetery or two before crossing the Charles. This was where my journey ended; the sun was setting past the river’s bridges, and it was time to get back to the hotel before it really started to get cold.

If I ever return to Boston, the second half of that red-brick road (and, by extension, the second half of Boston’s history) is definitely on my list.


If You Go…

  • Wear comfortable shoes
  • Try to many small dishes instead of one big meal, that way you get to taste all that the North End has to offer (I recommend pizza at Locale and dessert at Mike’s Pastry)
  • Download and print a map of the Freedom Trail here
  • Book your tickets for the Improv Asylum in advance

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