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Grayson Highlands 1 Night Backpacking Tour

Guided ·
5.0
See all guided camping trips in Damascus
Locally Owned
Wildlife
Small Group Sizes
Beginner Friendly
Free Cancellation
Instant Book
Multi-day
Duration: 2 days

Pricing

Person
$375

All Prices

Person
$375

Description

Backpack Into Pony Country: A 1-Night Grayson Highlands Adventure!

This is the kind of trip people sign up for on a whim—and end up talking about for years. Whether you’re coming solo, with a friend, or finally doing something you’ve been putting off, this 1-night guided backpacking trip through Grayson Highlands is designed to be approachable, unforgettable, and just the right amount of challenge. With a manageable 3 miles (4.8 km) in and 3 miles (4.8 km) out, you don’t need prior experience—just a willingness to get outside and try something new.
The trail winds through some of the Southeast’s most unique terrain, where open highland meadows stretch into sweeping mountain views and wild ponies roam freely. And yes—you’ll almost certainly see them. They graze near the trail, wander through camp, and create those moments where everything slows down and you realize you’re somewhere truly special. It’s not just a hike—it’s an experience that feels completely different from anything most people have done before.
What really sets this trip apart is how easy it is to just show up and enjoy it. All gear is provided—backpacks, tents, sleeping pads, meals, snacks—and your guide handles the details while also teaching you along the way. You’ll learn how to set up camp, filter water, and pack efficiently, all without feeling overwhelmed. With small groups capped at 8, the pace stays comfortable and personal, and first-timers consistently say they felt supported the entire time.
By the time you hike out, you won’t just have incredible photos—you’ll have new skills, new confidence, and a strong urge to plan your next trip.

Your Itinerary

  • Day 1: Meet your guide at the trailhead at 10:00 am. After a quick gear check and introductions, you'll set off into the Highlands. The 3-mile (4.8 km) hike to camp moves through open meadows and ridgeline views — with plenty of stops for photos, snacks, and your first pony encounters along the way. Once at camp, you'll learn how to set up your tent, filter water, and get a hot dinner going. The evening ends with sunset views that make the whole climb worth it.
  • Day 2: Wake up to a mountain sunrise and a hot breakfast made by your guide. Break camp, say goodbye to the ponies, and hike the 3 miles (4.8 km) back out. Most groups are back at the trailhead by early afternoon, tired in the best possible way.

Duration of Adventure

  • 2 Days & 1 Night

Location / Where to Meet

  1. Check in/ Departure Address: Grayson Highlands State Park
  • The meeting location will be within Grayson Highlands State Park in Virginia. Your guide will provide exact location details after booking!
  • This meeting point is approximately a 3 hour drive from Asheville, NC. The nearest town is approximately 45 minutes away in Damascus, VA. If needed, pre-trip or post-trip lodging can be found at Damascus (not included in price of trip).
  • You will meet at 10:00 am on the first day at the trailhead.

Ages & Requirements

  • The minimum age to participate is 18+ years old. This tour is for adults only!
  • The outfitter rates this trip beginner to intermediate, though no hiking or backpacking experience is needed!
  • Guests must be able to hike approximately 9 miles (14.5 km) round trip over 2 days.
  • There is a maximum of 8 hikers allowed on the tour and a minimum of 3. If the minimum number of hikers is not met, your guide will reach out to you within 2 weeks of your trip.

What’s Included

  • Wilderness First Responder Certified Expert Guide
  • High-Quality Backpacking Gear (Backpacks, Tents, Sleeping Pads)
  • Shared Gear (Stoves, Water Filters, First Aid Kit, Bathroom Trowels)
  • All Meals (Dehydrated Meals, Snacks, and Beverages)
  • Two-Person Tent (Single Occupancy Available at No Extra Cost)
  • We are able to accommodate a variety of dietary restrictions, however please keep in mind we are somewhat limited due to the nature of the activity. Dehydrated food is often used for the majority of meals, as it is lightweight and easy to carry (versus fresh food that is both heavy and perishable). When booking your trip, please note any allergies or dietary restrictions so we are aware and can adjust our food selection accordingly. 

Not Included

  • Gratuity - Never expected, but if you have a great experience, please consider gifting 10-25% to your guides!
  • Transportation to the meeting point / trailhead.
  • You will be provided a full detailed packing list after booking, some gear you will have to provide for yourself!

What to Bring / Wear

  • 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.
  • Sun / Rain Protection - Rimmed hat, sunglasses, neck covering (may attach to hat), and UV deflecting long sleeve shirts can all help to combat the harmful and strong sun rays. A poncho / rain jacket / rain pants is important to consider as weather can change quickly in the mountains!
  • Sturdy Hiking Shoes - Broken in/Used before with closed toes and grippy tread! 
  • Hiking Socks & Gaiters - Comfortable socks to prevent blisters and small shoe gaiters are helpful to keep rocks and sand from getting into the shoe and causing blisters or cuts!
  • Head Lamp
  • Mess Kit
  • Water Bottles/Water Bladder – 2 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.
  • Personal Medications – If you need certain medications along the hike, please be sure to have them with you.
  • Required Paperwork & ID Cards- Signed medical form if required, waivers, license, etc.

What Not to Bring

Don't bring many of the typical luxuries of everyday life that 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!

ADVENTURE PROVIDED BY Happy Hiking Company

FAQs

Who is this trip for?

This trip is perfect for those seeking a challenging, but very rewarding backpacking experience. With only one night in the backcountry, this trip is perfect for those new to backpacking and seasoned pro’s alike.

Don’t have a travel buddy? No problem! Many people choose to come on trips with us solo, or with a friend! If you’re travelling by yourself you’ll have a 2 person tent to yourself, or you can choose to bunk with another traveler to save some weight in your pack. If you’re travelling alone, a guide will reach out to coordinate this together. There is no additional fee for single occupancy if you would rather have the tent to yourself.

What is special about hiking in Grayson Highlands? 

Grayson Highlands is one of the most distinctive hiking destinations in the eastern United States. At elevations above 5,000 feet (1,524 m), the terrain opens into sweeping, treeless balds with panoramic views in every direction. But the true hallmark of Grayson Highlands is its wild ponies — a free-roaming herd that grazes across the high meadows and frequently wanders right up to hikers. While pony encounters can never be guaranteed, our guides report they have never visited without seeing them.

When is the best time to hike at Grayson Highlands? 

Grayson Highlands is beautiful in every season. Spring brings blooming wildflowers and rhododendrons; summer offers lush green balds and long daylight hours; fall is arguably the most stunning, with blazing foliage across the ridgelines; and winter brings snow-dusted views that feel truly remote. The wild ponies are present year-round. We run trips across multiple seasons — check the booking calendar for available dates.

Are there any insects or wildlife to be concerned about while hiking at Grayson Highlands? 

Ticks are present in the area, particularly in warmer months — do a full tick check at the end of each hiking day. Black bears live in the surrounding region; all food will be stored properly in bear canisters provided by your guide. The wild ponies, while enchanting, are wild animals — admire them from a respectful distance and do not attempt to feed or touch them.

Can I join as a solo person?

Absolutely! Trips with We are very solo traveler friendly. 

We often have people join on their own. These backpacking trips are a great way to meet people that have similar interests – often one of the biggest hurdles in backpacking is finding others to go with you on a trip. 

If you are travelling solo, your guide will reach out to you about sleeping accommodations. You can choose to sleep in a 2 person tent by yourself, or partner up with other solo travelers in the group to save some weight in your pack. There’s no up charge for single occupancy on any trip. Your guide will reach out to you to coordinate sleeping arrangements prior to your trip.

How can I train for my upcoming trip?

Backpacking is an endurance activity that requires sufficient training for it to be safe and enjoyable. 

There are all sorts of activities that can help better prepare you for your upcoming backpacking trip. Hiking with a pack on (with weight in it) will be the best preparation for a big backpacking trip. Running, HIIT, strength training, and yoga will also help prepare you for your trip as well. 

A full training guide will be sent out to those that have booked a trip with us.

Do I need prior experience backpacking?

Nope! Absolutely no prior backpacking experience is necessary before booking a guided backpacking tour with us. 

Often, people choose to book a guided hiking tour with us because they are beginners in the backpacking world. Using a guided tour is a great way to build your wilderness skills in a safe way, and meet other people with similar interests! We encourage both first time backpackers and seasoned pro’s to join us.

Can I bring my dog?

Unfortunately, dogs are not allowed on our hiking trips.

We understand the desire to share the adventure with your furry friends, but to ensure the safety and enjoyment of all participants, we have a no-dog policy. This allows us to minimize environmental impact, maintain group cohesion, and comply with park regulations.

Can I use my own gear on a backpacking trip?

Absolutely!

We provide high quality, lightweight gear for you to use. However, sometimes your personal preference could be to use what you’ve already tried and own. You’re more than welcome to use your own gear if you prefer.

What if I have dietary restrictions?

We do our best to accommodate most dietary restrictions. Vegan, vegetarian, and gluten free options are available for those coming on our trips. Please note any dietary restrictions upon booking and your guide will reach out to you to coordinate food for your trip.

Do you practice Leave No Trace? 

Yes. Happy Hiking Co. is committed to Leave No Trace principles on all trips. Guides carry backcountry bathroom kits (trowels and toilet paper), pack out all waste, and teach guests proper backcountry ethics throughout the experience.

Cancellation Policy

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.

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Availability

May 2027

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Location

Address

1904 Lees Chapel Rd

Greensboro, NC, 27405

US

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