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)

Rates for Private Guided HIkes

Customized private hikes for groups of 1-6 people

Book Your Hike

  • $90, solo hiker

    $130, two hikers

    +$30 each additional hiker

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

  • $115, solo hiker

    $180, two hikers

    +$40 each additional hiker

    Enough time to feel like an adventure, but we won’t tire you out for the rest of the day. Perfect basic length!

  • $150, solo hiker

    $225, two hikers

    +$50 each additional hiker

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

  • $250, solo hiker

    $375, two hikers

    +$75 each additional hiker

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

Contact for group rates of 7+ hikers.

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

Refundable $30 deposit is required for reserving your hike time.

$75 time and travel fee is added to all hikes in the southern Berkshires: Lenox, Great Barrington, and Egremont.

See our FAQ for more info.

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

Clarksburg State Park Pond Loop

Clarksburg, MA

1-2hr easy loop

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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

Contact for Group Rates

Ragged Mountain

via Greylock Glen, Adams MA

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DunBar Brook, Long/Short

2-3hr Moderate Out-And-Back , OR

4-5hr Moderate/Difficult Loop

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