Guided Hikes
in the Berkshires
Western Massachusetts, USA
Tie-Dyed Guide | Berkshire Hiking Adventures
Private Guided Hikes in the Berkshires
Solo Hikers + Couples + Families + Small Groups
Looking for the perfect guided hike in the Berkshires? Whether you're hoping to climb a mountain summit, enjoy a peaceful forest walk, or hike to scenic overlooks, Tie-Dyed Guide offers private hiking adventures in the Berkshires for hikers of all experience levels.
Hey what’s up!
Tie-Dyed Guide is your guy/guide for the best hikes in the Berkshire Mountains of Massachusetts. Epic views and peaceful forest paths! I’ll match you with the perfect route for your pace, your vibe and your schedule.
Guided Hiking Experiences in the
Berkshire Mountains, MA | USA
GET OUT HERE ON THE TRAIL 🥾
No stress, no worry, no planning—just a perfect customized hike with stunning views and time outside in nature! 🍁
Let Tie-Dyed Guide take care of all the details! I’m an experienced local trail guide who has guided hundreds of happy hikers since 2019 with great reviews. Reach out to me in the form below and we’ll figure out the perfect hike for you or your group. Then we’ll meet up at the trailhead and have an amazing hike together. I’ll lead the way and we’ll appreciate nature and have some nice conversation as we go. 🍃
FOR HIKERS OF ALL ABILITES. Easy, Moderate, and Challenging hikes. Great for Solo Hikers, Couples, Families, and Small Groups. 🍂
Rates for private group hikes (1-6 people)
Woods Walk (1-2 hours)
$95 solo hiker | $150 two hikers | +$40 each add’l hiker
Forest Explorer (2-3 hours)
$125 solo hiker | $200 two hikers | +$50 each add’l hiker
Half day Adventure (3-4 hours)
$160 solo hiker | $250 two hikers | +$60 each add’l hiker
Day Journey (6-8 hours)
$270 solo hiker | $410 two hikers | +$90 each add’l hiker
Fill out the form to
schedule your hike
We’ll get back to you as soon as possible.
We can often accommodate last minute requests—even next day! Don’t hesitate to reach out!
Want to hike here?
Let’s hit the trail!
Just fill out the form below to start the booking process 👇
Climb Mt. Greylock
Hike to the highest peak in Massachusetts
Stunning Views • Great Exercise • Adventurous Trails
Big time accomplishment!
Meet your guide!
Hey what’s up! I’m a Berkshires local who knows all the best trails. I’ve led hundreds of hikers over 7+ years, with dozens of 5-star reviews. I’m safety certified and love chatting with visiting hikers as we go. Read more…
Tie-Dyed Guide
can take you on
amazing hikes in
these Berkshire towns
of western Massachusetts
and in Southern Vermont
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, Massachusetts is my go-to spot because of the 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!)
SOUTHERN VERMONT
Experience the amazing GREEN MOUNTAINS of Vermont! Vermont truly is a special place with its stunning mountains—both in the summer and the winter. We offer a couple amazing fire tower hikes, including the super beautiful, and surprisingly doable Stratton Mountain climb with its incredible view from the fire tower atop Southern Vermont’s highest mountain at 3,940’. Also ask about the easy Mt. Olga fire tower hike near lovely Wilmington.
LENOX, MA
Lenox, Massachusetts 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.
We also hike from Great Barrington, Cheshire, Pittsfield, Lee, Stockbridge, Florida, Clarksburg, and Wilmington, Vermont. Just ask!
A few thoughts I posted on TDG Blog about why you’d want to hire a local trail guide.
Ready to hike?
Fill out the form to schedule
We’ll get back to you as soon as possible.
We can often accommodate last minute requests!
Reviews for Tie-Dyed Guide
Airbnb in MA (5.0★) | Airbnb in DC (4.97★) | Google (5.0★)
Rates for Private Guided HIkes
Customized private hikes for groups of 1-6 people
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$95, solo hiker
$150, two hikers
+$40 each additional hiker
Easygoing hike. You are looking for a nice time in nature without too much exertion.
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$125, solo hiker
$200, two hikers
+$50 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!
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$160, solo hiker
$250, two hikers
+$60 each additional hiker
Now we’re getting into a real hiking adventure! Difficulty ranges from moderate to strenuous.
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$270, solo hiker
$410, two hikers
+$90 each additional hiker
Big time adventure! You are looking for a real experience deep in the woods. Strenuous.
Let’s do this!
schedule your hike
We’ll get back to you as soon as possible.
We can often accommodate last minute requests!
Frequently Asked Questions (FAQ)
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It’s super easy! Just contact us using the booking form on this site with your preferred date, group size, and length.
I’ll email you back and we’ll determine a time and route.
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This is YOUR hike! You can use the “List of Hikes” or “Hiking Experiences” sections to choose yourself. However, most hikers just choose a duration (1-2 hours, 2-3 hours, 3-4 hours, and 6-8 hours). After you reach out, we’ll have a brief exchange over email (or phone call if you’d like) to help select the perfect hike for you or your group!
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All hikes are private hikes for you or your group (up to 6 hikers), and start at $95. The specific Hikes and Experiences on the navigation menu have prices listed on those pages.
Many customers, however, select from our 4 options based on duration:
Woods Walk (1-2 hours)
$95 solo hiker | $150 two hikers | +$40 each add’l hiker
Forest Explorer (2-3 hours)
$125 solo hiker | $200 two hikers | +$50 each add’l hiker
Half Day Adventure (3-4 hours)
$160 solo hiker | $250 two hikers | +$60 each add’l hiker
Day Journey (6-8 hours)
$270 solo hiker | $410 two hikers | +$90 each add’l hiker
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Tie-Dyed Guide provides private, personalized hikes that suit your group!
We are a private hiking guide service. Whatever hike you book, it will be just your group (or just you if you’re solo)—no big random group of strangers!
(If you are interested in group hikes, TDG has the Hike-A-Month club, which provides one short, easy group hike on the second Tuesday of every month at 5:30pm.)
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A $30 deposit is due for all hikes to reserve a time. It is fully refundable up to 24hrs before the hike. We ask for full payment at the conclusion of the hike (see below).
You can cancel for any reason up to 24hrs before the hike with a full refund of your deposit. If you cancel within 24hrs the deposit is forfeited or can be used for a future hike.
Weather cancellation results in a full refund no matter when.
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You can cancel with no penalty up to 24 hours before your hike and receive a full refund of your deposit. If you cancel within 24 hours, the deposit is non‑refundable—but you’re welcome to apply it toward a future hike.
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You can pay the refundable deposit by Venmo or Credit Card.
The remainder is due at the end of the hike. You can pay by Venmo, Cash, or Credit Card.
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We meet at the trailhead that we decide upon.
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Not much to stress about, just show up at the trailhead with boots or sneakers and at least 20oz of water—and be ready for a great time! We’ll be in contact beforehand, so all the details will be worked out. It will be simple!
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Just let us know! Whether you’d like an easier pace, specific terrain (waterfalls, lookouts), or a more vigorous experience, we’re flexible and happy to plan accordingly for your group.
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Yes, we love dogs!
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Absolutely! We take out hikers of all ages and abilities! Just let us know the general level of you or your group and we’ll find something perfect for you! (In fact I have a special “Hiking for Beginners” experience because I love to get new people OUTSIDE and exposed to NATURE!)