Book a Guided Hike
in the Berkshires today!
Explore the Amazing Trails of the Berkshires of Massachusetts — With a Groovy Local Trail Guide!
Let “Tie-Dyed Guide” take care of all the details! Reach out to me in the form below and we’ll figure out the perfect hike for you or your group. No stress, no worry, no planning—just a perfect customized hike with stunning views and time outside in nature!
For hikers of ALL ABILITES! Great for Solo Hikers, Couples, Families, and small groups.
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!
Dunbar Brook
Mt. Greylock
Hey what’s up!
Tie-Dyed Guide has got you covered for personalized hikes on best Berkshire trails. Epic views and peaceful forest paths! I’ll match you with the perfect route for your pace, your vibe and your schedule.
Appalachian Trail
Ragged Mountain
Want to hike here?
Let’s hit the trail!
Just fill out the form below to start the booking process 🠟
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.
We also hike from Great Barrington, Cheshire, Pittsfield, Lee, Stockbridge, Florida, Clarksburg, and Wilmington, VT. Just ask!
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!
Can’t Wait? Want to Reserve your hike Right Now?
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.
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…
Reviews for Tie-Dyed Guide
Airbnb in MA (5.0★) | Airbnb in DC (4.97★) | Google (5.0★)
Pricing for Private HIkes
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$30 per person, groups of 4-6
$40 per person, groups of 2-3
$55 per person, solo hikers
Easygoing hike. You are looking for a nice time in nature without too much exertion.
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$45 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!
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$60 per person, groups of 4-6
$75 per person, groups of 2-3
$100 per person, solo hikers
Now we’re getting into a real hiking adventure! Difficulty ranges from moderate to strenuous.
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$110 per person, groups of 3+
$150 per person, groups of 2
$200 per person, solo hikers
Big time adventure! You are looking for a real experience deep in the woods. Strenuous. Customers provide their own lunch.
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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You can contact us using the booking form on this site with your preferred date, group size, and whether you'd like a Short, Standard, Half‑Day, or Day Journey hike. We’ll email you back and we’ll determine a time and route. If you prefer to reserve a timeslot first yourself, feel free to do so on the booking app.
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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 (Short, Standard, Half-Day, Day-Journey) and after you reserve or contact us, 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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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!)