Guided Hikes in the Berkshires

Scenic. Local. Easy to Book

Explore some of the best hiking trails in the Berkshires with a local guide.

Our small-group hikes are designed for couples, friends, and visitors who want to experience the Berkshires without having to figure out where to go, where to park, or which trail is right for them.

Choose Your Berkshire Hike

From quick scenic climbs to longer adventures, choose the hike that fits your day.

Cheshire Cobble

Short, Steep & Scenic

A quick but rewarding climb with beautiful Berkshire views. Perfect if you want a real hike without taking up your whole day.

◷ Approx. 1 hour
$49 per person
2-person minimum

Book Cheshire Cobble

Book Cheshire Cobble!

Mahanna Cobble

Scenic Berkshire Adventure

A scenic hike with more trail time, elevation, and beautiful Berkshire views. Perfect for guests looking for a moderate adventure and a rewarding overlook.

◷ Approx. 1 hour

$49 per person

2-person minimum

Book Mahanna Cobble

Book Mahanna Cobble!

Whats Included

✓ Local guide
✓ Small-group experience
✓ Trail selection and navigation
✓ Scenic stops along the way
✓ Light trail snack
✓ A relaxed pace based on your group

Hiking Schedule

Weekdays: 3:30 PM
Saturday & Sunday: 10:30 AM

Select weekday mornings may also be available.

Looking for a different time?
Give us a call — custom start times may be available.

Hiking Season

September through November, weather permitting.

Late-season hikes may be available depending on trail conditions.