Winter Wonderland Hike
Berkshire Mountains, Massachussetts
& Southern Vermont
GET OUTSIDE in the Winter Wonderland of the Berkshires or Southern Vermont with a groovy local guide! ❆ ❆ ❆
Winter Wonderland Hike
❆ Get outside this winter! ❆
🌲 Explore Nature! 🌲 Get Exercise! 🌲
Enter into the Winter Wonderland of snow-covered trails, bright crisp air, and peaceful beauty that feels completely different from any other season. It really is magical!
Hiking in the winter is a bit tricky though, and conditions are always changing. Instead of getting bogged down with all the decisions and logistics, hike with a fun local guide who will take care of all the details!
Winter Wonderland Hike is an easy, enjoyable 1–2 hour hike designed to make winter hiking accessible and fun—so you can just enjoy the BEAUTY of WINTER!
Tie-Dyed Guide in an experienced local trail guide who will provide personalized guidance, handle all your questions (what to wear, best time of day, etc.), choose the perfect trail for your or your group, and adjust the pace to your needs—making a potentially intimidating experience feel simple and welcoming.
Winter Wonderland Hike
🥾 Difficulty/Length:
Easy to Moderate (1-2 Hours).
🌨️ Easy Cancellation:
Weather can be variable in the winter. Full refund of your deposit if conditions are not good for hiking.
🌲 Locations:
1) Greylock Glen, Adams, MA
2) Hoosac Range, North Adams, MA
3) Olga Mtn Fire Tower, Wilmington, VT
4) Custom location - we decide!
⛏️ Equipment:
Just bring good boots, and wear layers. TDG will provide spikes if needed.
Winter Wonderland Hike Rates:
$100 solo hiker
$145 two hikers
+ $35 each add’l hiker
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…
Ready to hike?
Fill out the form and we’ll get back to you as soon as possible.
We can often accommodate last minute requests!