Take a hike in the
Berkshires
with a friendly local
trail guide
Pricing for Private HIkes
Contact about scheduling and booking.
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$30 per person, groups of 4-6
$40 per person, groups of 2-3
$55 per person, solo hikers
Mostly easy, but some climbing possible if you’d like.
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$40 per person, groups 4-6
$60 per person, groups 2-3
$80 per person, solo hikers
Enough time to feel like an adventure, but we won’t tire you out for the rest of the day. Perfect basic length!
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$60 per person, groups of 4-6
$75 per person, groups of 2-3
$100 per person, solo hikers
Difficulty ranges from moderate to strenuous
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$110 per person, groups of 3+
$150 per person, groups of 2
$200 per person, solo hikers
Strenuous. Customers provide their own lunch.
TDG Can Take you on Amazing Hikes in these Berkshire TOwns
NORTH ADAMS, MA
Home to Mt. Greylock, the highest peak in Massachusetts, North Adams is my hometown and perfect for adventurers looking for either rugged, moderate, or easy hikes—all with breathtaking vistas. We specialize in customizing hikes on Mt. Greylock’s amazing array of trails. And the Appalachian Trail goes right through town! Best town for Berkshires hiking!
ADAMS, MA
In the shadow of mighty Mt. Greylock, Adams is my go-to spot because of Greylock Glen recreation area, with its trails for all abilities. Best spot for summit climbs and beautiful easy valley walks in meadows with summit views or alongside peaceful Peck’s Brook. (Also the home of Susan B. Anthony!)
LENOX, MA
Lenox is such a beautiful town to visit, with amazing attractions like Tanglewood, The Mount, Kripalu, and so many amazing hotels and inns. But there are also a couple great parks for hiking. Kennedy Park is good for easy forest walks with a few views, and Lenox Mountain/Pleasant Valley has a moderate climb with an incredible view!
WILLIAMSTOWN, MA
Classic New England charm, home to Williams College, Williamstown has got the exciting West face of Mt. Greylock, with amazing trails from Haley Farm, and some of the best views in the park from Stoney Brook. On the other side of town you have easygoing Mountain Meadow Preserve, Broad Brook, beautiful Taconic Meadow, and a nice moderate climb to an amazing view with Pine Cobble.
We also hike from Great Barrington, Cheshire, Pittsfield, Lee, Stockbridge, Florida, Clarksburg, and Wilmington VT. Just ask!
Featured Hikes
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Ragged Mountain
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Dunbar Brook
Follow beautiful, serene Dunbar Brook as it tumbles down through the Florida Mountain highlands. There is a 2 hr short version—easy/moderate, and 5 hour strenuous loop.
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The Wooded Trails of Rock Creek Park
The original Tie-Dyed Guide hike. Limited availability (i.e., when I get around to visiting my old home, Washington DC)
Clarksburg State Park Pond Loop
Clarksburg, MA
1-2hr easy loop
Reviews for Tie-Dyed Guide
Airbnb in MA (5.0★) | Airbnb in DC (4.97★) | Google (5.0★)
A few thoughts I posted on TDG Blog about why you might want to hire a local trail guide.
Group Hikes in the Berkshires w/ Tie-Dyed Guide
A guided hike in the Berkshires is the perfect activity for your corporate retreat or school trip.
Create an incredible memory for the whole group!
GROUP RATES APPLY AT 7 OR MORE HIKERS
Ragged Mountain
via Greylock Glen, Adams MA
DunBar Brook, Long/Short
2-3hr Moderate Out-And-Back , OR
4-5hr Moderate/Difficult Loop