Walking Boston’s Freedom Trail – History That Hits Different

Our family laced up our walking shoes and explored Boston’s Freedom Trail—a journey through American history with stops at Paul Revere’s House, the Old North Church, and more. Here’s how this immersive experience added depth to our weekend and became a highlight for both adults and kids.

Thomas Scott

5/26/20252 min read

One of the highlights of our Boston trip was walking the Freedom Trail. As parents, we love the idea of sneaking some education into our travels—and Boston makes it easy. This 2.5-mile trail winds through some of the most iconic historical sites in the country, and it’s all laid out like a self-guided museum.

(*Sidenote: we booked through Viator.com because they allow cancellation up to the day before on trips like this so we could make sure we went during the best weather of our trip to be outside and walking around. I checked other's prices and all were within $2/person of each other for the same tour.)

We started at Boston Common, the oldest city park in America. From there, it was like stepping into a time machine. We passed the Massachusetts State House, Paul Revere's House, the Old North Church, and eventually made our way to Bunker Hill and the USS Constitution.

The kids were surprisingly into it—especially with the help of our knowledgeable tour guide, Candace, who is a History Student there in Boston. There’s something powerful about walking the same brick paths that revolutionaries once did. It wasn’t just history—it was a story, and we were walking through it.

At about the 1.5 hour mark, we stopped at Quincy market for a restroom and snack break. Quincy Market is a historic marketplace and food hall located in the heart of downtown Boston, adjacent to Faneuil Hall. Built in 1826 and named after Boston Mayor Josiah Quincy, the market was originally designed as a central location for vendors to sell produce, meats, and other goods to the growing city. Today, it seems that it's one of Boston’s most visited attractions, blending the city’s rich history with a vibrant modern food scene where you can browse booth by booth. Hot buttered lobster roll anyone?

Pro tip: Uber to the meeting point in Boston Commons. There is a garage under the park, however the tour ends near the harbor which is over a mile from the start point. So if you don't fancy a mile walk back after the 2.5 mile journey, just grab another Uber once you finish up the tour.

In the end, the Freedom Trail gave us more than facts—it gave us a connection to the roots of the country, and a moment of stillness in an otherwise packed sports weekend.