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 “Guided Hikes”, “Mountain Climbs” or “Hiking Experiences” sections on the navigation menu to choose for yourself. Or, many 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!)
What Kind Of Hike Is Right For Me? 🌲
Choosing the right hike is all about what makes you feel good out there. At Tie-Dyed Guide, I’ll help you pick a Berkshire trail tailored to your fitness, trail comfort, and schedule. We will chat through your options together, but here is a quick look at how to find your fit:
A Gentle Outing (1-2 hours): This is best for shorter walks, flat terrain, and taking it easy. You can expect smooth paths, minimal hills, and plenty of pauses to look around and soak in the woods.
Options: Kennedy Park Stroll in Lenox, MA, or the Greylock Glen Meadow Meander.
Moderate Hike with Hills (2-3 hours): Perfect for regular walkers looking for a bit of scenery and exercise. You can expect rolling trails, manageable climbs, and some uneven footing with a rewarding view.
Options: The Cheshire Cobble Overlook, Ragged Mountain Loop, or Dunbar Brook.
A Bigger Challenge (3-6 hours): Built for hikers who love sustained exercise and a good workout. You can expect mountain adventures with steeper climbs, rugged terrain, and longer distances.
Options: Climb Mt. Greylock, Lenox Mountain Summit Climb, or venture a bit north for a Climb up Stratton Mountain.
A Few Quick Things to Consider
Your Age: Age is just a number! Tell me how you stay active, how your knees feel on downhills, and if you have any balance or stamina concerns. For groups, we always plan around the comfort of the least experienced hiker.
Your Available Time: Whether you have two hours or a full day, we will budget time for steady walking, snack breaks, and taking photos.
Amount of Uphill: Do you want to stick to flat paths or rolling hills? Or are you up for tackling sustained mountain climbs that test your legs and lungs?
Your Fitness Level: Think about how much endurance you have and what kind of sustained physical activity feels rewarding rather than exhausting.
Still unsure? Let’s talk! You don’t need to have a specific trail in mind before reaching out. Click the Contact button below and tell me about a walk you enjoyed recently, what you want to see, and anything you’d rather avoid—I'll get back to you with some suggestions and we’ll figure it out!