We Dare You To Take This Road Trip To Boston’s Most Abandoned Places

Although Boston is a densely populated city, it still has its share of derelict and forgotten spots. You can drive up to or hike through these abandoned places, although – in many cases – the buildings themselves are out-of-bounds for safety reasons. If you like to discover Boston’s history through its abandoned places, you’ll love this trip around the city.

The journey takes just under two hours in light traffic (not including stops) and covers 62 miles. Here’s a handy map to guide your trip.

Note: Please abide by all trespassing laws and be mindful of private property signs when exploring.

1. Old Bear Dens (Franklin Park)

Our road trip to the most abandoned places in Boston begins at the Franklin Park Zoo. You could visit Franklin Park multiple times without having a clue that Long Crouch Woods contains abandoned enclosures that once housed bears. When Franklin Park Zoo opened in 1912, the bears were an early attraction. However, the enclosures stopped being used in 1971 and were left to gently decay in the woods.
Old Bear Dens, Playstead Rd, Boston, MA 02119, USA

An unexpectedly dramatic stone staircase hidden in the middle of the woods leads to dens decorated with elaborate stonework. This faded grandeur paired with the forest setting make this a hauntingly beautiful spot.

2. Brook Farm (West Roxbury)

Wikimedia Commons/Midnightdreary

Visit the remains of a utopian commune from the 1840s that was part of the transcendentalist movement. Life at Brook Farm involved a careful balance of work, relaxation, and community responsibility. Nathanial Hawthorne spent time here and the commune served as inspiration for a similar community featured in his book: The Blithedale Romance.

Unfortunately, Brook Farm wasn’t an economic success and it closed after only a few years. The white building still standing today is the farm’s old print shop. Learn more about what you’ll discover when you visit this hauntingly abandoned place near Boston.
West Roxbury, 450 Lagrange St, West Roxbury, MA 02132, USA

3. Medfield State Hospital (Medfield)

Wikimedia Commons/Magicpiano

The town of Medfield owns Medfield State Hospital, an old asylum turned park. Unlike many abandoned places, visitors can walk around, although access to the derelict buildings is off-limits. If this hospital looks familiar, that’s probably because parts of “Shutter Island” were filmed here. Learn more about what makes the abandoned Medfield State Hospital so eerie.
Medfield State Hospital, 1 Stonegate Dr, Medfield, MA 02052, USA

4. Wompatuck State Park (Hingham)

Wikimedia Commons/Pi.1415926535

There’s more to Wompatuck State Park than first meets the eye. During World War II and the Korean War, part of this land was used as an ammunition depot for the U.S. Navy. As you explore the park, you can glimpse a few derelict bunkers and also the train tracks that connected the depot to Hingham Shipyards and Fore River. This haunted park in Massachusetts is not for the faint of heart!
Wompatuck State Park, 204 Union St, Hingham, MA 02043, USA

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