Boston Freedom Trail according to BosGuy

The Freedom Trail is a 2.5 mile path that winds through several downtown neighborhoods in Boston, identifying 16 historic markers that tell the story of the American Revolution.

The Freedom trail meanders through Beacon Hill, the North End and Charlestown but it can be a bit repetitive with multiple cemeteries and churches each with a slightly different historic significance. To liven things up, over the years, I’ve provided friends a modified version of the Freedom Trail. All that walking and learning works up a thirst so I “enhance” the walk by strategically selecting hydration stops and pointing out unique (but historically irrelevant) sites. Below is the Boston Freedom Trail according to BosGuy, which uses the city’s official Freedom Trail map.

One can start the Freedom Trail from either the Boston Common or Bunker Hill Monument. I suggest starting in Charlestown so you are back in the center of Boston when done. Grab a ride to Bunker Hill in Charlestown (pronounced, CHARLES-TOWN, unlike the city in SC) or hop on the Orange Line to the Bunker Hill Community College station and walk there. Feel free to walk up the 221 foot obelisk designed to commemorate the 1775 Battle of Bunker Hill. I’m slightly claustrophobic so I prefer to sit on the hill and look out at the harbor.

After, walk down to the U.S.S. Constitution (commissioned in 1797). I enjoy going aboard but you can get a better selfie from the dock so if boats aren’t your thing, snap a photo then walk over the N. Washington Bridge to the North End (you’ll pass the Converse HQ on your right – in case any of you are fans of their classic Chuck Taylor sneaker). The next stop on the trail is Copp’s Hill Burying Ground, but I skip it since there are other burying grounds on the tour, and I walk friends down Hull Street to show the “House of Spite” a.k.a. Skinny House on the way to the Old North Church.

The Old North Church is probably best known for alerting Paul Revere on how the English would attack, hanging lanterns in their steeple, “one if by land and two if by sea”. From the church, walk down the Paul Revere Mall on your way to Paul Revere’s House. Dating back to 1680, it is one of the oldest buildings in Boston. This home is interesting because of its history but if you’re getting hungry skip going inside and walk to The Modern Pastry on Hanover Street. Buy a cannoli or some other sweet (this is a cash-only establishment) and enjoy it on the Rose Kennedy Greenway. It makes for an ideal resting place. From that vantage point, I like to show friends the Union Oyster House, which has been operating since 1826 and has a booth on the second floor where President Kennedy liked to dine with Jackie and others.

Faneuil Hall, the next stop on the tour is a tourist trap but deserving of a visit. Despite having just finished a cannoli (I strongly recommend eating desserts first), if hungry the neighboring Quincy market and (the slightly less busy) Boston Public Market offer many options for lunch. If you’re not hungry but all that walking has made you thirsty take a photo by the Sam Adams statue and pop into the Sam Adams Boston Tap Room.

The next two stops are close to the Sam Adams Tap Room and essentially one in the same. The Old State House and Boston Massacre Site are photo worthy but require nothing more. The ground floor of the Old State House is now a MBTA T stop for Boston’s Orange and Blue Lines. About two blocks away are the Old South Meeting House and the Old Corner Bookstore both of which I routinely skip and walk up School Street to Boston Latin School Site & Ben Franklin Statue. This also happens to be Boston’s Old City Hall, and is a gorgeous example of French Second Empire architecture. Back in the day I’d bring friends to The Littlest Bar (which sadly closed). Walk up School Street to King’s Chapel and Burying Ground. It’s interesting to see the cemetery and the chapel that dates back to 1686, although this is a newer building that opened in 1754.

The Parker House Hotel is next to King’s Chapel and has the distinction of being the longest continuously operating hotel in the US. It happens to be where the Boston Creme Pie was invented in 1856 and where both Ho Chi Minh (from 1912-1913) and Malcolm X in the 1940s worked briefly. The first a Vietnamese revolutionary and politician and the other, a prominent African American muslim minister and activist.

The next stop, Granary Burying Ground, is one block down on Tremont Street. This cemetery has many famous graves including the Franklin (as in Ben’s parents) family grave, an ostentatious tomb for John Hancock and a grave for Samuel Adams but my favorite is the tiny grave for Elizabeth “Mother” Goose (1665 – 1758). Next to the cemetery is the next stop on the Freedom Trail, Park Street Church, which I typically skip. Perhaps it’s my Catholic roots, but I find old Protestant churches stark and uninteresting on the inside.

The second to last stop on the Freedom Trail is one worth entering, The Massachusetts State House. While this isn’t the largest State House it is architecturally beautiful and has many historical points of interest. You can sign up for a building tour, here. The top of the state house dome is capped with a pine cone. For those who enjoy trivia, the reason for that is explained here. After finishing the tour, go next door to the 21st Amendment Pub. Toast the repeal of prohibition and for completing the Boston Freedom Trail. The final stop, The Boston Common, established in 1634, is one block away.

2 responses to “Boston Freedom Trail according to BosGuy

  1. My (now) husband and I walked the Freedom Trail 30 years ago, on our first out-of-town trip together. It was fascinating and a great way of sharing with each other a love of history. Thanks for posting this, bringing back fond memories. 🙂

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  2. I’ve always loved to story of the Spite House!

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