Experience the Best and Most Beautiful Hikes in the Berkshires with a Groovy Local trail Guide.

Berkshire Mountains, Massachusetts

Adams + North Adams + Williamstown + Lenox

Let’s Go for a Hike!

Fun , adventurous, beautiful Hikes for people of all ages and abilities.

Solo Hikers + Groups + Private Hikes

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!

New TDG Blog entry

DunBar Brook, Long/Short

One of my fave spots, out of the way, remote, not too steep (unless we do the longer, more strenuous loop). There is a bottom and a top trailhead. Either way, there is a moderate climb as we follow the gorgeous Dunbar Brook as it tumbles down into the Deerfield River. Incredible sights and sounds.

2-3hr Moderate Out-And-Back (from $40 per person) , OR

4-5hr Moderate/Difficult Loop (from $60 per person)

NEW Tie-Dyed Guide Hiking Experience!

Personal Training Session

Great Hike + Great Exercise

Hiking is not only a great way to clear your mind and connect with nature—it’s also one of the best ways to get your regular EXERCISE. Hiking for exercise can be the cornerstone to making and keeping your body HEALTHY and STRONG while spending time in the Great Outdoors having fun! Gym routines can be boring and monotonous—no motivation or energy for treadmill or lifting under the artificial florescent lights. Why not take your fitness routine outside in NATURE where the beauty of the forests stimulates the mind and body, allowing you to enjoy the outdoors and have FUN while working out!

A man standing on a forest trail holding a gray jacket, wearing a sleeveless tie-dye shirt, black shorts, and athletic shoes, next to text advertising a tie-dyed guide hiking experience and fitness and exercise hike.

  • "This experience was incredible! Jeff was an amazing, knowledgeable, and insightful guide. Great conversationalist that will open your perspective and mind. The views are breathtaking and unforgettable. Highly recommend this experience for all ages and hiking levels."

    -Thuy, The Wooded Trails of Rock Creek Park

  • "Jeff was a great guide and lead our group of six on a very cool hike. We went off the beaten path and Jeff added some fun detours spontaneously to better accommodate our preferences. He was very knowledgeable about the area and told interesting stories along the way. On top of providing a great tour, Jeff is also a great person and it was fun to spend time with him. "

    -Sebastian, Hike to Ragged Mountain

  • "This was such a great hike and I am so happy that I booked it! Jeff was not only a great guide, but he was great company. It was a perfect end to my weekend in the Berkshires. The hike was pretty moderate with some challenging parts, which were totally worth it for the amazing views at each peak! I completely recommend checking this out!"

    -Carolyn, Hike to Ragged Mountain

  • "This tour is great! I did it as a solo traveler with jeff but it would also be very nice for groups as well. Jeff knows the trails very well, so you dont have to worry about getting lost and can just enjoy the walk and the scene. Also, the conversation with him was great and flowing! Value for the money!"

    -Matan, The Wooded Trails of Rock Creek Park

  • "Jeff is a fantastic hiking partner and guide. I told him what I was looking for, my ability level and time preferences and he suggested 4 options. He’s knowledgeable and chatty (but not too chatty), he matched my pace, pointed out beautiful views and where to take care with footing. I will definitely be hiking with him again."

    -Donene, Hike to Ragged Mountain

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

Three people sitting on rocks in a mountainous landscape with pine trees and blue sky in a trail on Vermont on a guided hike with Tie-Dyed Guide.
Wooden trail sign at a forested hiking path in Woodford, Vermont surrounded by evergreen trees and mountain landscape in the background.
Person sitting on rocky outcrop overlooking a forest with autumn foliage under a cloudy sky on a hiking trail in the Green Mountains of Vermont on a Tie-Dyed Guide hike,
Two people walking on a forest trail past a fallen tree and a large uprooted tree on the side of the trail.
A narrow forest trail with roots and moss, marked with blue trail markers on trees, next to a body of water with trees on the far shore.
Close-up of a smiling man with a beard in a wooded outdoor setting, wearing a puffer jacket and hoodie, with fallen trees in the background.
Two hikers, a woman in a purple shirt and a man in a beige shirt, walking on a dirt trail in a dense autumn forest with colorful fall foliage.
Two smiling men with beards standing outdoors in a forest near a wooden structure.
Wooden trail sign with directions in a lush green forest. Left arrow pointing to South and West, right arrow pointing North. Labels: 'S AT/ LT N', 'MASS. LINE 3.1', 'ROUTE 9 11.2'.
Wildflowers including daisies growing on a hillside overlooking a deep valley with lush green woods and power lines, under a partly cloudy blue sky.
An older man with a beard, wearing a blue cap, orange glasses, a gray T-shirt, and blue shorts, holding a walking stick outdoors on a cloudy day. He is carrying a black backpack and standing at a stone railing near a grassy area with trees in the bac

Pricing for Private HIkes

4 Options:

Short • Standard • Half-Day • Day-Long

Contact for group rates for 7+ hikers

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

    Mostly easy, but some climbing possible if you’d like.

  • $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!

  • $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

  • $110 per person, groups of 3+

    $150 per person, groups of 2

    $200 per person, solo hikers

    Strenuous. Customers provide their own lunch.

Featured Hikes

3 ways to book

↓

1.Book Here

Reach Out Using the Form Below

Please include:

1) When you’d like to hike

2) The size of your group

3) Which you prefer: Short Hike, Standard Hike, Half-Day Adventure, or Day Journey, or which type of Hiking Experience you’re interested in (in navigation menu).

4) If you have a specific hike in mind, please let me know which. Otherwise, let me know your preferred level of difficulty (easy, moderate, strenuous) and any other features that interest you (views, streams, climbs, etc.).

I’ll get back to you with several customized hiking options. After we set a time and hike, you can book here or pay with venmo or cash when we meet.

2. Reserve A Time Slot on Booking App

If you want to reserve a time slot directly, you can do it yourself HERE.

After you reserve the time slot, I will reach out to you to determine the length or type of hike you are interested in, as well as payment and cost info.

3. Book Through Airbnb

Book on Airbnb Experience. I am currently offering a private 2 hour hike of your choice (easy/moderate/strenuous) in Mt. Greylock Park.