Lenox Mountain SumMit Hike
Lenox, Massachusetts
Hike to one of the Berkshires most rewarding summits
Lenox Mountain Summit Hike
Looking for a true mountain adventure—with an awesome payoff view—while you're visiting Lenox, MA?
This is it!
This private guided hike takes your group to the summit of Lenox Mountain—one of the classic hiking destinations, right in the heart of the Berkshires of Massachusetts.
Starting from the beautiful forests of Pleasant Valley Reserve, just a few minutes from Lenox, with an easy warm-up walking along boardwalks beside a bird-populated pond, we'll make a steady (but not too long!) climb ascending up the lovely Overbrook Trail to the summit of Lenox Mountain.
At the top we'll take a well-deserved break to soak in the views stretching across the Berkshires. We’ll chill, catch our breath, enjoy a snack, take photos, and appreciate the accomplishment of hiking Lenox Mountain.
An invigorating, but very doable climb in the heart of the Berkshires!
Although the climb is relatively short (1.5 miles up, 1.5 down), it features a steep-ish incline in places, so it’s suited for hikers with a reasonable level of fitness (feel free to reach out if you are wondering if you are up for it—most hikers are).
Don't worry about keeping up—I guide every hike at your group's pace, with plenty of opportunities to stop, catch your breath, and enjoy the surroundings.
This is an ideal experience for visitors staying in Lenox, MA who want more than a casual walk. If you’re looking for an active morning, something a bit off the beaten path (it’s never crowded), or simply hoping to experience one of the Berkshires best summit hikes, this adventure delivers.
Want to explore even more? You’ve got options!
Classic Summit Loop to Lenox Mountain (~2 hours)
The classic summit loop is a great choice for most hikers—a great 3-mile loop with a solid, doable climb, and it can be done in about 2 hours. But because every hike is private, we can easily customize the adventure if you'd like to spend more time on the trail.
Lenox Mountain + Yokun Seat (~3 hours)
We can continue past Lenox Mountain summit, along the mostly flat Yokun Ridge Trail to Yokun Seat, adding another incredible scenic overlook, which peers into another side of the valley. It adds about an hour to the trip and is a great option for hikers who want to explore more of the Yokun Ridge.
Lenox Mountain + Mahanna Cobble (4-5 hours)
For experienced hikers looking for a bigger day in the mountains, we can continue along Yokun Ridge to Mahanna Cobble, with a great vista to the south and east. This longer route adds approximately two hours and transforms the hike into an unforgettable half-day adventure featuring additional viewpoints, quieter trails, and one of the finest ridge walks in the southern Berkshires.
Highlights
🥾 One of the premier guided hikes near Lenox
⛰️ Reach the summit of Lenox Mountain
🌲 Beautiful forests in Pleasant Valley Wildlife Sanctuary
📸 Spectacular summit views and excellent photo opportunities
🥾 Optional longer routes to Yokun Seat or Mahanna Cobble
☮️ Private guided hike at your own pace
Classic Summit Hike: 3 miles | ~2 hours
Yokun Seat Extension: 4 miles | ~3 hours
Mahanna Cobble Adventure: 7 miles | 4-5 hours
Best for: Active travelers, couples, families with older children, and anyone looking to experience one of the Berkshires' classic mountain hikes while visiting Lenox.
Classic Summit Loop
$125, solo hiker
$195, two hikers
+ $50 each add’l hiker
Yokun Seat Extension
$145, solo hiker
$210, two hikers
+ $55 each add’l hiker
Mahanna Cobble Adventure
$195, solo hiker
$295, two hikers
+ $75 each add’l hiker
Booking/Info Form below 👇
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…
Ready to hike
Lenox Mountain?
We’ll get back to you as soon as possible.
We can often accommodate last minute requests, so don’t hesitate to reach out!