Take a hike in the

Berkshires

with a friendly local

trail guide

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!

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We can often accommodate last minute requests!

Featured Hikes

  • Mountain landscape with rocky foreground and dense green forest, under cloudy sky. Mt. Greylock from Ragged Mountain in Greylock State Reservation in North Adams, MA

    Ragged Mountain

    A fun, challenging hike. 3-4hrs. Amazing vistas.

  • Forest scene with a stream, rocks, and trees showing autumn foliage, in Florida, MA, on a guided Tie-Dyed Guide hike.

    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.

  • Sunlight streaming through autumn trees in a forest with a rocky stream in Adams, MA in the Berkshires on a Tie-Dyed Guide hike.

    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)

Pricing for Private HIkes

4 Options:

Short • Standard • Half-Day • Day-Long

Contact for group rates for 7+ hikers

All hikes fully cancellable up to 24hrs before your hike.

A refundable $30 deposit required for reserving your hike time.

See our FAQ for more info.

Contact about scheduling and booking.

Two hikers descending a mountain trail at sunset in the Berkshires, surrounded by trees, with a scenic view of distant mountains.

  • $30 per person, groups of 4-6

    $40 per person, groups of 2-3

    $55 per person, solo hikers

    Easygoing hike. You are looking for a nice time in nature without too much exertion.

  • $45 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!

  • $60 per person, groups of 4-6

    $75 per person, groups of 2-3

    $100 per person, solo hikers

    Now we’re getting into a real hiking adventure! Difficulty ranges from moderate to strenuous.

  • $110 per person, groups of 3+

    $150 per person, groups of 2

    $200 per person, solo hikers

    Big time adventure! You are looking for a real experience deep in the woods. Strenuous. Customers provide their own lunch.

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