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

Customized guided hikes for solo hikers + couples + families + small groups

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

Tie-Dyed Guide 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. It’s also home to the world-famous MASS MoCA contemporary art museum. 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 and The Clark art museum, Williamstown looks up to 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.

…and more:

We also hike from Great Barrington, Cheshire, Pittsfield, Lee, Stockbridge, Florida, Clarksburg, and Wilmington, VT. Just ask!

Climb Mt. Greylock

Hike to the highest peak in Massachusetts

Stunning Views • Great Exercise • Adventurous Trails

Big time accomplishment!

Climb Mt. Greylock

New TDG Blog entry

Rates for private group hikes (1-6 people)

Four people walking on a narrow dirt trail through a lush green grassy field with trees and a blue sky in the background.

Woods Walk (1-2 hours)

$90 solo hiker | $130 two hikers | +$30 each add’l hiker

Hikers walking on a forest trail with sunlight shining through tall trees.

Forest Explorer (2-3 hours)

$115 solo hiker | $180 two hikers | +$40 each add’l hiker

Group of hikers resting on a mountain summit with lush green landscape and blue skies in the background.

Half day Adventure (3-4 hours)

$150 solo hiker | $225 two hikers | +$50 each add’l hiker

Two hikers on a rocky trail surrounded by trees in a mountainous forest during sunset, with distant mountain peaks and a sky with orange and pink hues.

Day Journey (6-8 hours)

$250 solo hiker | $375 two hikers | +$75 each add’l hiker

Ready to hike?

Fill out the form to get started…

We’ll get back to you as soon as possible.

We can often accommodate last minute requests!

Next Hike: Thursday, November 6th!

TDG Hike-A-Month Club

One group hike. Every month. Just $5/month.

Mountain landscape with pine trees, with text 'Tie-Dyed Guide Berkshire Hiking Adventures'
Learn more

Reviews for Tie-Dyed Guide

Airbnb in MA (5.0★) | Airbnb in DC (4.97★) | Google (5.0★)

  • Screenshot of a positive travel review written by Sam from Cambridge, MA, in May 2025, about a trip to the Berkshires, expressing gratitude to Jeff for organizing the trip and mentioning his flexibility and hiking experience.
  • Screenshots of two positive reviews for a hiking guide named Jeff. The reviews praise Jeff's knowledge, insightfulness, and friendly guidance during outdoor experiences at Rock Creek.
  • Screenshot of a 5-star review for a hiking service, with text praising Jeff's friendliness, listening to customer's preferences, accommodating a disability, and providing a successful and safe hike; includes a response from Jeff and a profile picture of Jennifer from Silver Spring, MD.
  • Screenshot of online reviews with ratings, including reviews from Cassandra, Niki, and Saumya, praising a guide named Jeff and a park experience in Washington DC.
  • Screenshots of online reviews discussing a hiking experience with a guide named Jeff, mentioning positive feedback and recommendations.
  • Screenshot of online reviews about a hiking guide service, featuring reviews from Thomas, Cynthia, and Anna, all praising Jeff for his guidance, responsiveness, and the positive hiking experience.
  • Screenshots of customer reviews for a hiking or outdoor experience with high ratings, highlighting beautiful locations, good hikes, and friendly guides.
  • Online reviews and testimonials from customers for a guiding or hiking service, dated September and August 2024.
  • Collection of customer reviews with star ratings, names, dates, and comments about their positive experiences.
  • Screenshots of three travel reviews from different users, praising a hiking trip and a guide named Jeff, including locations Indianapolis, IN; Austin, TX; and a general mention of the United States.
  • Screenshots of two reviews for a hiking guide named Jeff, praising his assistance and responsiveness during trail planning.
  • Screenshots of two online reviews for a hiking guide named Jeff, one from Carolyn in Norwalk, CT, and one from Donene in Somerville, MA, both praising his guidance and companionship.
  • Screenshot of two hiking reviews with five-star ratings. The first review is by Nicole from North Providence, RI, praising Jeff for a hike and trail guidance with her dog. The second review is by Katherine from the United States, complimenting Jeff for a friendly, knowledgeable hike with great views and snacks.

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 $115

Read More

  • "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’d want to hire a local trail guide.

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!

Read more...
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.

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
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

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.

3 ways to book

↓

1. Fill out this form

to schedule your hike

We’ll get back to you as soon as possible.

We can often accommodate last minute requests!

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.

Reserve Time

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.

Book on Airbnb

See you out on the trail!