Kennedy park Stroll
Private Guided Hike
in Lenox, Massachusetts
Kennedy Park Stroll
In Lenox, MA
with options for a longer walk—up to 4 hours
Duration: 1 to 2 hours
Here’s an ideal easy, relaxing hike if you’re staying in the Lenox, Massachusetts area of the Berkshires.
Kennedy Park—which is sneakily pretty big—is just about right in town. It sits right at the center of the Berkshire region upon rolling hills overlooking the valley and the town—a few incredible views!
Even though it is easily accessible once you are off the trailhead and get into the park’s rolling ridges you may as well be in the middle of a remote forest.
It’s great for a relaxing walk in the forest, and a perfect complement to the classic old New England town experience you get with Lenox, Lee, or Stockbridge.
Interestingly, it’s the site of an old 19th-century horse farm, which became a luxury resort—Hotel Alpinwall—at the turn of the century. It’s got some very interesting features, such as the ruins of the hotel, a gazebo which has a clear view to Mt. Greylock 20 miles to the north, a natural spring, and, of course, miles of beautiful forested trails that criss-cross the park.
You’ll appreciate having an experienced guide, as the network is extensive and complicated. Tie-Dyed Guide has been leading hikers of all levels for 7+ years, with dozens and dozens of 5-star reviews.
Reach out below, and I’ll pick the perfect loop for your group!
1-2 hour short hike:
$150, solo hiker
$200, two hikers
+ $50 each additional hiker
Longer options below 👇
The old Hotel Alpinwall
Interested in a longer hike in Kennedy Park? Sure!!
With its endless looping trails you can wander for hours in Kennedy Park.
2-3hr Forest Explorer: $200 solo hiker | $250 two hikers | + $60 each add’l hiker
3-4hr Half-Day Adventure: $250 solo hiker | $300 two hikers | + $70 each add’l hiker
Meet your guide!
Hey what’s up! I’m a Berkshires local who knows all the best trails. I’ve led hundreds of hikers over 7+ years, with dozens of 5-star reviews. I’m safety certified and love chatting with visiting hikers as we go. Read more…
Schedule Your Hike
in Kennedy Park, Lenox
We’ll get back to you as soon as possible.
We can often accommodate last minute requests, so don’t hesitate to reach out.