Hike the Appalachian Trail

w/ thru hiker legend “K-Dog”

Hike on the Appalachian Trail with an incredible hiker who completed the 2,200 mile journey in 2023.

A man with a long beard and a backwards baseball cap smiling next to a wooden sign that says 'KATAHDIN' with hiking trail information, indicating he completed a trek in the Appalachian Trail.

I’m so psyched that my friend Keith, aka K-Dog (every thru hiker gets a nickname), agreed to offer his incredible experiences as bona-fide Appalachian Trail (AT) “thru hiker”—i.e., someone who has completed the world famous 2,200 mile trail from Georgia to Maine. Keith did it back in 2023, not long after I met him in Greylock Glen in 2021.

I wrote about our (very) short segment together on Keith’s journey on TDG Blog when he came through North Adams on a misty—but incredibly beautiful—morning in June. Really honored to have been part of his AT hike!

For a visitor or group of visitors to the region this is amazing: you get to go on a beautiful hike led by Keith (an incredibly friendly guy) where he will talk all about his experiences for the 5 straight months he was out under the trees pounding out the miles on the AT. He can also give advice about how to prepare yourself for a long-haul hike if you are curious about it. He has great insight and skill!

Even better you’ll be hiking along a little segment of the Appalachian Trail with him! Yes, hike the world-famous trail in the beautiful northern Berkshires around Mount Greylock—the highest peak in Massachusetts.

Logo featuring a mountain with pine trees and a lake, with the text 'TIE-DYED GUIDE' and 'Berkshire Hiking Adventures' written below.
Appalachian Trail logo with a stylized tree and text indicating National Scenic Trail.

As I said, Keith is a great guide and incredibly friendly. He’s always up for telling folks about the 18-mile a day pace he kept up for those 5 months, the incredible people he met, what it’s like to live a life of backpacking through forests—the trials and travails of the trail! Also, he’s a old-time local to the area and he knows the trails better than anybody! So I know he’s got a few good stories from back in the day, and all sorts of lore about Greylock.

Just reach out, to check about availability and to pick a perfect segment of the trail for whatever kind of hike you or your group is interested in—easy, moderate, or even a some climbing if you’d like.

Starting at $30 per person: Short Hike (1-2 hours) or Half-Day Adventure (3-4 hours) pricing.

  • A man with a beard wearing a yellow rain jacket, shorts, and a cap stands on top of the Katahdin mountain summit, holding trekking poles in the air, in foggy weather. He is behind a weathered wooden sign that reads 'KATAHDIN' and indicates the mountain's elevation and trail information.
  • Two men smiling outdoors near a wooden structure with a green forest in the background. One man has a beard and is wearing a pink hoodie, and the other man has a long beard, is wearing a white cap, and a bright yellow shirt with a backpack.
  • An older man with gray hair and a beard, wearing a blue cap, gray t-shirt, and blue shorts, is holding a large stick and pointing it towards the sky. He has a black backpack and orange sunglasses. He is outdoors on a cloudy day, standing next to a stone wall and an informational sign, with greenery and trees in the background.
  • Five men standing outdoors on a gravel path with trees and green bushes background, smiling and posing for a group photo. They are dressed casually and appear to be on a hike or outdoor adventure.
  • A man with a beard wearing a bright yellow jacket and a cap, smiling, standing next to a wooden sign that reads 'KATAHDIN' and provides trail information, indicating he is at Baxter Peak, the end of the Appalachian Trail.