Navigating the Boston Freedom Trail

My favorite thing to do in Boston is to explore the city’s Freedom Trail. When younger, I was that dork that visited state capitals to learn about our government. I didn’t do a lot of traveling back then but I somehow found a way to get down to Washington D.C., twice! Naturally, when I moved to Boston, I set out on the Freedom Trail. As I visited each historical site, I would hop into a nearby pub so I could read up on the building or monument. Well, as you can imagine, a lot of historical shenanigans went down in Boston. So, by the end of the day – well, let’s say – I got the full effect of what it’s like to be a Bostonian. Hence, the Drunkin’ Freedom Trail was born!

Where to start on the Freedom Trail

Start at Cheers, where everybody knows your name, and grab a pint

Follow the Red Brick Road

Work your way to the Massachusetts State House, you can’t miss it, it has a big gold dome; be sure to check out the 54th Regiment (across from state house) and Mary Dyer (next to state house) memorials. Make a right to head down to Granary Burying Ground to view some pretty famous headstones

Massachusetts State House

Where to Pit-Stop on the Freedom Trail

Stop at the Omni Parker House Hotel for the original Boston Cream Pie. For a short detour and an authentic Irish pub, pit-stop at JJ Foley’s and grab another pint. Make sure not to miss the Irish Famine Memorial.

Old Boston

Head to the Old State House to observe where the Boston Massacre occurred. Moreover, this is also where the foundation of ‘innocent until proven guilty’ was enforced through John Adams. Veer around the corner to Faneuil Hall Marketplace where you can see a bunch of street performers. Pit-stop at the Union Oyster House, the oldest oyster house in the country, and Bell and Hand, the oldest tavern in the US. Don’t miss the Holocaust Memorial in front of the bar and oyster house – it’s a moving tribute to the victims and survivors of World War II and, in my opinion, one of the most emotionally impactful installations I’ve experienced.

Boston State House

Old State House

Nathaniel Hall

Nathaniel Hall

Added Bonus on the Freedom Trail

A short walk away is the North End where you can find Paul Revere House, Old North Church and Mike’s Pastry – the best pignolis Italian cookies in town. You may want to swing by Locale and grab a pizza and a craft beer. It’s been a long day after all.


If you have the time, take the walk across the bridge to Charlestown and check out the Bunker Hill Monument. And end your day at Warren Tavern, where George Washington and Paul Revere used to take a load off.

Bridge to Charlestown

Bunker Hill

Bunker Hill

I want to hear what you think! Comment below and let me know what your favorite parts were and if I should add a place you loved. 

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