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 in Boston, although – in many cases – the buildings themselves are out-of-bounds for safety reasons. If you like to discover the city’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.

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 makes this a hauntingly beautiful spot and is part of one of the most famous abandoned places in Boston.

Take a look at this video by @j-mass:

2. Brook Farm (West Roxbury)

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 piece of abandoned Boston.

3. Medfield State Hospital (Medfield)

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. If you're searching for "abandoned places near me" around Boston, you can't beat this abandoned hospital.

Take a look at this video by @ChristopherSetterlund:

4. Wompatuck State Park (Hingham)

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!

5. Fort Revere Park (Hull)

Fort Revere isn’t just historic and abandoned; it’s also rumored to be haunted. Perched on Telegraph Hill in Hull, the earliest fortifications on this site date back to the 1770s.

During the Revolutionary War, French soldiers stationed here succumbed to smallpox and were buried under the hill. This tragedy spawned tales of ghosts, and many have claimed to see mysterious, moving shadows and hear disembodied voices speaking in French. You can wander around this disused fort to your heart’s content. Have you ever visited this haunted fortress in Massachusetts?

Take a look at this video by @j-mass:

Have you ventured into any of these abandoned places in Boston? Share your adventures in the comments -- we would love to hear from you! And before you hit the road on this trip, check out our list of road trip essentials!

If you enjoy a good scare, you should check out these disturbing and haunted cemeteries around Boston that are sure to give you chills. More interested in offbeat history? Then read about the strangest things that ever happened in Boston.