When you were a kid, did you ever fantasize about stumbling across a crumbling ruin in the forest? There’s something strangely fascinating about the weathered remains of old buildings and monuments no matter what your age. Luckily, Massachusetts is home to quite a few ruins that you can reach on foot. Even better, the journey is just as scenic as the destination, in these cases. Here are five hikes to ancient ruins in Massachusetts that you’ve got to experience at least once:

1. Eyrie House Ruins, Mt. Tom Reservation, Holyoke
Paul Cooper/Flickr
These ruins may look like the remains of an ancient castle, but the Eyrie House was actually a 19th-century hotel.
Rob/Flickr
Located on Mount Nonotuck, the hotel opened in 1861 and was considered extremely fashionable for decades. Unfortunately, a horse cremation gone wrong resulted in an inferno that engulfed the hotel in 1901. Its owner, William Street, hadn't insured the property, and was left without the funds to rebuild.

To visit these ruins, start at the entrance along Christopher Clark Road, and continue until you hit the Ranger Station. The journey to the ruins themselves is about 2 miles. You can walk along an old road that is now closed to traffic, so this is an adventure well-suited to casual hikers.

Address: 125 Reservation Road, Holyoke, Massachusetts, 01040
2. Dinosaur Footprints Trail, Holyoke
Monicuba23/TripAdvisor

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The "ruins" here are more than ancient - they're prehistoric. The Dinosaur Footprints Reservation in Holyoke is an 8-acre wilderness that is actually peppered with real dinosaur tracks. Hundreds of footprints are embedded in the sandstone throughout the park. You can hike along the trackways that dinosaurs themselves used to travel. The reservation is open during daylight hours between April 1 to November 30, and there are plenty of trails that will take you to the coolest of the footprints. Check with the information center at the reservation for a guide on how best to tackle viewing the footprints.

Address: Route 5, Holyoke, Massachusetts, 01040
3. Becket Land Trust Historic Quarry and Forest, Becket
RamblinDan/TripAdvisor
If your idea of a great ruin involves more rust than crumbling marble, this hike is perfect. The Becket Land Trust Historic Quarry and Forest is a park unlike any other. Littered throughout the forest are vintage automobiles, machinery, and buildings from the area's days as a functioning quarry. The automobiles and machines are especially amazing, as some of them are well over 100 years old. Hiking here also affords pretty spectacular views of the Berkshires, and the trails are kept clear and blazed by volunteers.

Address: 456 Quarry Road, Becket, Massachusetts, 01223
4. Greycourt State Park, Methuen
Erasergirl/Wikimedia
Greycourt State Park was constructed around the abandoned ruins of the Charles H. Tenney estate, also known as the Tenney Castle. Though most of the once-imposing structure has been lost, a portion of one wing remains, and it's open to public exploration. These ruins are restored, but they're all the more striking for having been spruced up. You can walk the trails around the park and "hike" (okay, it's really more of a stroll) up to the ruins to investigate.

Address: 37 Pleasant Street, Methuen, Massachusetts, 01844
5. Bear Cages, Boston
Linden Tea/Flickr
Yes, there are "ancient" ruins hidden in Boston. Inside the famed Franklin Park Zoo is a collection of odd, abandoned structures that look like they were dropped straight out of Ancient Rome. In fact, these large enclosures once housed bears. In the early 1900s, the public flocked to the bear cages to see the fearsome creatures prowl around the large courtyard behind iron bars. The attraction was eventually closed in 1954, but the stone bear den was never demolished. Today, you can visit the abandoned cages in Long Crouch Woods, the 26-acre woodland that sits above Seaver Street in Roxbury. Just follow the long, broad path that leads through the forest from the entrance to the park.

Address: 1 Franklin Park Road, Boston, Massachusetts, 02121

What do you think about these hikes to ancient ruins in Massachusetts — are you surprised by some of these places? Share your thoughts in the comments below!

And if you’re interested in more spectacular hikes in The Bay State, take a look at the 13 most amazing trails in Massachusetts.

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Hikes to Ancient Ruins in Massachusetts

Tori Jane | March 31, 2021

Where can I find ancient ruins in Massachusetts?

Well, that depends on your definition of "ancient", but if you mean well over a century old, then Massachusetts is the place to be! We've got a bunch of amazing ruins that you can explore; some of our favorites include the Eyrie House Ruins, nestled inside the Mt. Tom Reservation, which was once a lavish hotel in the 1800s before fire destroyed it in 1901. You can hike to what's left of this historic place to check it out for yourself. Another great spot for ruins-enthusiasts is the Tenney Castle, a literal castle in Greycourt State Park. For more picks from our list of favorite Massachusetts ruins, check this article out!

What are the best hikes in Massachusetts?

There are literally thousands of trails in our beautiful state to choose from, though there is definitely some that stick out above the rest in terms of awesomeness. The Great Blue Hill, via the Skyline Trail, is the top-rated hiking trail in the state, featuring an incredible lookout view of the entire Boston skyline. It's best-hiked from April to October. Another top-rated hike is the Mount Watatic/Nutting Hill hike, via the Wapack Trail. The views are incredible, and the lush greenery is like something out of a fairy tale. Finally, another one of our favorites is easily the hiking on Mount Norwottuck, which leads you to views from the highest peak in the Holyoke mountain range.

What are some abandoned places in Massachusetts?

Massachusetts is an old, old state with plenty of noteworthy abandoned places to speak of. For example, the Metropolitan State Hospital in Lexington truly feels like something out of a horror movie. It was once a highly controversial mental institution, and today, some of the deserted buildings in the complex still stand, while others have been converted to modern apartments. Steinert Hall is a gorgeous, crumbling old music hall, lurking several floors below a Boston piano shop. It's a secret in plain sight, as visitors aren't allowed, and employees don't like to talk about it.

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Featured Addresses
125 Reservation Rd, Holyoke, MA 01040, USA
US-5, Holyoke, MA, USA
456 Quarry Rd, Becket, MA 01223, USA
37 Pleasant St, Methuen, MA 01844, USA
1 Franklin Park Rd, Boston, MA 02121, USA