Experience the Best and Most Beautiful Hikes in the Berkshire Mountains 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

This is more of an aesthetic, forest bathing-type hike than a botany lesson. We’ll head out on an easy, 1-2 hour hike with some undulations. Perhaps we’ll wander up one of the brookside trails in Greylock Glen, hike around the Mauserts Pond in Clarksburg, or head for the Mountain Meadow preserve in Williamstown.

It’s just about just being immersed in the springtime sights, sounds, and smells. Relax, take a walk, unplug and chill out…

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!

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.

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

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

  • "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

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,
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me and keith on his appalachian trail journey.jpg
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Greylock Hike with Tie-Dyed Guide in the Berkshires.jpg

Pricing for Private HIkes

3 Options:

Short • Half-Day • Day-Long

Contact me to schedule/book.

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+

    $40 per person, groups of 2-3

    $55 per person, solo hikers

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

  • $60 per person, groups of 4+

    $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

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, Half Day Adventure, or Day Journey.

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.

Booking Through Airbnb

Book on Airbnb Experience. I am currently offering a 2-4 hour hike of your choice (easy/moderate/strenuous) in Mt. Greylock Park.