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 👇

Two people hiking on a snowy forest trail with sunlight filtering through tall trees on a private guided hike with Tie-Dyed Guide in Lenox in the Berkshires of Massachusetts
Two people hiking on a snowy forest trail with sunlight filtering through tall trees on a private guided hike with Tie-Dyed Guide in Lenox in the Berkshires of Massachusetts
Old Hotel Alpinwall in a hilly forest landscape with tall trees in the foreground, in kennedy park in Lenox Massachusetts in the Berkshires
Vintage postcard of Hotel Aspinwall in Lenox, Massachusetts, featuring a large tree-lined building under a blue sky with clouds.
Vintage postcard of Hotel Aspinwall in Lenox, Massachusetts, featuring a large tree-lined building under a blue sky with clouds.

The old Hotel Alpinwall

Trail map of John Drummond Kennedy Park in Lenox, MA, showing various trails, parking areas, roads, and landmarks.
Trail map of John Drummond Kennedy Park in Lenox, MA, showing various trails, parking areas, roads, and landmarks.

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.