At the western tip of Massachusetts, at the northern tip of the Berkshires, is the Mount Greylock State Reservation. This preserve has more than 12,000 acres of virgin New England forest, 50 miles of hiking trails, and more than 1,500 acres recognized as National Natural Landmarks. Marking the upper center of this reservation is the highest peak in Massachusetts, Mount Greylock. At its nearly 3,500-foot summit is the historic 100-foot-tall War Memorial and rustic stone lodge, both nearly 100 years old.
Unlike most other hiking areas in the region, the southern section of the Mount Greylock State Reserve does not use the Appalachian Trail as its main hiking trail and very few major side trails branch off of it on this trail. area. However, one caveat about the area is that the trails in this area range from very easy to very difficult. It’s not always easy to discern which is which from the trailhead and a novice hiker who has already beaten down an easier trail can find himself in trouble if he’s not careful.
Probably my favorite trail in the area is the Round Rock Trail. It’s a simple one-mile round-trip hike with some nice extras. Short and sweet, this trail is perfect for a brisk afternoon hike or to burn off a few calories if you’re nearby. Now when most people go on a nature hike, they specifically don’t want to see man-made intrusions, but two of these elements make this trail unique, especially considering how short it is. If you are heading uphill from the south trail entrance, the first item you will come across is the Old Town marker. Erected in 1912, this pillar designates the New Ashford-Cheshire town line. I know it sounds simple enough, but things like this in the middle of nowhere always catch my eye.
Just a few hundred feet further down the road, you will come across the site of a tragedy. In 1945, a small plane crashed here and all that remains is the rotten frame and a small wooden cross. Although sad, one cannot help but ask what was the story behind the accident, if anyone survived or how many perished. I know it’s morbid, but places like this or an old abandoned house in the middle of nowhere attract lovers of the mystery that we all carry inside. By the time you’re done pondering the problem, you’ll be back in the parking lot and probably thinking that you got a lot out of such a short drive.
Another trail that adds a little artificial flavor to the scenic beauty is the old Dynamite Trail. About a mile and a quarter long, this trail runs parallel to the Appalachian Trail, however the two intersect at the south trailhead. Not far from this intersection, you will see the old storage box used in the early 1930s to store the dynamite used to carve the roads in the area.
If you’re in the mood for more scenic adventures, we recommend starting at the top of the southern section at Mount Greylock. In addition to the hostel and the war memorial, the summit itself offers spectacular views. If you follow the trails to the southwest of the mountain, you will find at least half a dozen scenic trails that intersect. However, it is easy to get lost among so many trails that cross and vary in terms of difficulty, so it is best to be vigilant.
