Pathway Through Boston

What to do, what to do? Boston has endless amounts of streets to wander, and since so many have been mapped out, it’s hard to find something a little more unique, out of the way, and original. So, let’s start your day off by taking the Green Line to Park Street. When you emerge from the underground station, resist the urge of H&M, DSW, and Macy’s, and head straight into the thick of the Boston Common! You’re not going to be popping a squat amongst the masses of people stretched across one of Boston’s most well-known locations today—you’ll be heading on a diagonal through the park and toward Charles Street.

This isn’t the regular street-walking adventure. Charles Street is a mere means to an end. While here, you might as well take in the sights along the way. Gorgeous antiques line endless shop windows, as bakeries tempt and tantalize the senses with their delicious treats. The appeal of one-of-a-kind, handcrafted goods will try to beckon you and lure you with their promises of rare finds and bargain deals, but resist! There’s always the trek back to explore.

As you reach the end of the always-quaint Charles Street, a fairly large intersection will face you. Cross over in the direction of the massive glass-structure, which also houses the Red Line’s Charles/MGH T station. You’ll inevitably end up crossing underneath the overpass when you finally see it. What you’ve been walking toward this whole time: the historic Liberty Hotel.

It may seem like an odd outing—why would I even want to see a hotel? Well, before this building had been transformed into a four-star residence—architecturally gorgeous and aesthetically pleasing—it was actually a jail.

Housing some of Boston’s most notorious criminals (including former mayor James Curley), you’ll be able to see signs of its former state the moment you approach its barred windows. You’ll practically be able to imagine yourself, a prisoner, being looked down upon by the watch-guards from the open floors above. The bars of its former jail cells awaken its storied past.

A wall of “fun facts” and stories from its heyday will excite any history buff and passerby alike, so I won’t spoil all the fun. Right outside the hotel is a beautiful transformed courtyard where prisoners used to exercise, and in the lobby is the pricey but tasty restaurant that’s cleverly named “Clink.”

Now, whether you choose to stay and mingle in the lobby, enjoy their Bloody Mary bar, give in to your curiosity, and explore the rest of their floors, or depart for the trip home is up to you. Whatever the case may be, you won’t soon forget stepping foot into the national landmark and former Charles Street Jail—the Liberty Hotel.