backpack with wild ponies
GRAYSON HIGHLANDS, VA
backpack with wild ponies
GRAYSON HIGHLANDS, VA
2 days
1 night
9 miles
ROUND TRIP
7 Guests
MAXIMUM
- Intro to Backpacking Education
- WILD PONY ENCOUNTERS
- near damascus, va
- beginner friendly
$375
Roam the Highlands: A 2-Day Backpacking Adventure with Wild Ponies
Join us for a 2-day, 1-night backpacking trip through the breathtaking landscapes of Grayson Highlands—one of the most unique and scenic areas in the Southeast. This co-ed trip is designed to keep the mileage approachable, giving you time to enjoy the experience while exploring rolling highland balds, rocky outcrops, and wide-open mountain views.
Along the way, you’ll hike through some of the park’s most iconic terrain, with plenty of opportunities to spot the famous wild ponies that call this area home. In a small, supportive group, you’ll build confidence with your gear, learn practical backcountry skills, and settle into the rhythm of life outdoors. Whether you’re coming solo or with a friend, this trip is all about adventure, connection, and unforgettable moments on the trail.
Food
All meals are provided by Happy Hiking Company and will be distributed the morning of your trip. You’ll choose from a selection of lightweight, backpacking-friendly options including dehydrated meals, snacks, and drinks (coffee included!).
We can accommodate many dietary needs, but options may be somewhat limited due to the nature of backpacking food. Please note any allergies or restrictions when booking so we can plan accordingly.
Gear
We provide high-quality backpacking gear at no additional cost, including backpacks, tents, trekking poles, and sleeping pads. Your guide will fit and distribute gear before you hit the trail.
All shared equipment—such as stoves, water filters, first aid supplies, and bathroom kits—is also included and will be divided among the group.
This hike starts at the overnight backpackers lot in Grayson Highlands State Park. Exact address and directions will be provided after booking.
For pre-trip lodging, Damascus, VA is nearby as an option. Please note pre-trip lodging is not included in the cost of this trip.
This trip is a great fit if you’re looking for a moderate challenge with a big payoff—think a few miles of hiking, carrying a pack, and settling into camp in the backcountry.
Coming solo? You’ll be in good company—many guests join on their own, while others come with a friend. You’ll have the option of a two-person tent to yourself or sharing with another participant to lighten your pack. There’s no extra cost if you prefer your own tent.
After booking we will provide a full detailed packing list specific to your trip. Gear that you should plan on bringing yourself includes:
- Sleeping bag – 20 degree bags are recommended in April, May, Sept, Oct, and Nov time frames – the mountains are chillier than you think!
- Clothing – one outfit to hike in, one to sleep in (you do not need extra changes of clothes), along with adequate layers for the weather. Avoid cotton if possible – if cotton gets wet it will stay damp and cold
- Rain gear – jacket/rain pants
- Hiking boots or shoes
- Head lamp
- Mess Kit
- Water bottles/water bladder – 3 Liters recommended, one in a heat safe container (ex – Nalgene) to use as a hot water bottle on cold nights. Once your trip is booked your guide will reach out with route specific water guidelines.
- Any personal medication
Many of the typical luxuries of everyday life are not needed in the backcountry! Feel free to leave your makeup, deodorant, and other products at home. A toothbrush/toothpaste is the only recommended toiletry for your trip.
Extra electronics and other forms of entertainment are not needed – take this time to disconnect and enjoy nature – screen free!
The cost for this trip is $375, and will run if there are 3 or more hikers in the group. If the minimum number of hikers is not met, your guide will reach out to you within 2 weeks of your trip.
This cost includes all food, as well as most of the gear needed for the trip. The details on what is included and what is your responsibility to bring is outlined above. Once booked your guide will send you a detailed packing list as well.To book a trip with Happy Hiking Co., a 20% non-refundable deposit is required. Trips are required to be paid in full within 3 weeks of your scheduled trip date. If needed, you can cancel for a full refund (minus the 20% deposit) prior to 3 weeks of your trip departure date.
More than 3 weeks prior to departure, if you need to transfer to another trip date there is a $30 transfer fee. Within 3 weeks of your departure date, transfers are not available.
Within 3 weeks of your trip date, a 50% refund will be issued. Within 1 week of your trip date, no refund will be offered barring cancellation of the trip by Happy Hiking Co.
Happy Hiking Co. runs tours rain or shine! Should extreme weather circumstances arise, your guide will reach out to coordinate the details and changes to your itinerary.
If your guide does an exceptional job, please show your appreciation with a tip.
Our team of highly trained professional guides never expects but always appreciates a tip. Industry standard gratuity for a guided backpacking trip is 15-20% of trip price.
What to look forward to
Step into a landscape that feels a little wild and wide open in the best way. Grayson Highlands is known for its rolling grassy balds, rocky outcrops, and sweeping mountain views that stretch for miles. We’ll keep a relaxed, enjoyable pace, with plenty of time to take in the scenery, snap photos, and just enjoy being out there.
As the day winds down, we’ll settle into camp, share a warm meal, and take in a sunset that feels straight out of a postcard. With fresh mountain air, open skies, and a small group of like-minded hikers, it’s the kind of experience that leaves you feeling refreshed, reconnected, and already dreaming about your next trip.
What awaits you...
Meet the wild ponies: One of the most unforgettable parts of Grayson Highlands is the chance to see the famous wild ponies up close. These gentle, free-roaming herds are a staple of the area and often wander right through the balds near camp. Watching them graze, interact, and move through the landscape is a truly special experience—and a reminder of just how unique this place is.
Learn the ropes: This trip is also a great opportunity to build confidence in your backpacking skills. From packing your bag to setting up camp and getting comfortable with your gear, you’ll learn practical, real-world skills in a supportive, low-pressure environment. Whether it’s your first trip or you’re looking to brush up on the basics, you’ll leave feeling more capable and ready for your next adventure.
why choose happy hiking Co.?
Happy Hiking Co. is a locally owned, boutique guide company—every trip is planned and led by our team, not outsourced. Our guides are highly experienced, Wilderness First Responder (WFR) certified, and deeply familiar with the areas we explore. We keep our groups small and our approach hands-on, so you get real guidance, not just someone pointing the way.
From trip planning to your final mile on trail, everything is designed to feel smooth, safe, and well thought out. Our goal is simple: help you feel confident, supported, and fully present out there—whether it’s your first trip or your fifth.