5,000+ Handpicked Adventures 4.8 Avg Across 185K Reviews Book Direct With Local Experts Every Booking Funds Conservation

5K+ Adventures 4.8 Avg Eco-Funded

Adventure, Curated

Explore 5,000+ human-powered experiences — handpicked outdoor adventures for all skill levels with max stoke, zero hassle.

Local Legends, Real Reviews

We partner with the best in the business — trusted local outfitters and guides who know the trails, tides, and terrain. Backed by 185,000+ reviews, averaging 4.8⭐

Book Direct, Best Price Guarantee

Get the best price, availability, and flexibility you need by booking directly with the outfitter or guide.

Protect What You Love

Your adventure gives back. Every booking supports conservation and keeps wild places wild.

Grayson Highlands 1 Night Watercolor & Backpacking Experience

Guided ·

5.0

Buchanan• Covington

Locally Owned

Wildlife

Small Group Sizes

Beginner Friendly

Free Cancellation

Instant Book

Duration: 2 days

Pricing

Person

$375

Description

Paint What You Feel: A Grayson Highlands Watercolor Backpacking Experience!

This trip is for anyone craving something a little different—something slower, more intentional, and way more memorable than a typical hike. It’s not just about covering miles or learning technique. It’s about stepping into one of the Southeast’s most striking landscapes and actually taking the time to see it. Over two days in Grayson Highlands State Park, you’ll hike into open alpine-style meadows, set up camp surrounded by mountain views, and spend time painting what’s right in front of you.

Along the way, you’ll likely find yourself sharing the landscape with the park’s famous wild ponies, grazing nearby or wandering through camp like they’ve always been part of the scene. And in a way, they are. On this trip, they’re not just a cool sighting—they often become your subject. With a travel watercolor kit provided, you’ll settle in for guided but relaxed painting sessions that focus less on perfection and more on presence. No experience needed, no pressure—just a chance to slow down and respond to the landscape in your own way.

Everything is set up so you can simply show up and enjoy it. All backpacking gear, meals, and supplies are included, and groups are capped at 8 to keep things personal and supportive. Whether you’ve never backpacked or never painted before, you’ll be guided every step of the way. By the time you hike out, you won’t just have photos—you’ll have something you created, shaped by the place itself.

Itinerary

Day 1: Meet your guide at the Grayson Highlands trailhead (location provided after booking) at 10am. Hike approximately 4.5 miles (7.2 km) to camp, with wild pony encounters along the way and multiple viewpoints worth stopping for. After setting up camp and settling in, the afternoon is given over to a guided watercolor session — painting the landscape around you while the light is at its best. Dinner and sunset views close out the evening.
Day 2: Hot breakfast at camp, a final morning in the Highlands, and then the 4.5-mile (7.2 km) hike back out. You'll leave with painted pages in your pack, photos on your phone, and a pretty clear sense of why people keep coming back to Grayson.

Duration of Adventure

2 Days & 1 Night

Location / Where to Meet

Check in/ Departure Address: Grayson Highlands Overnight Backpackers Lot
The meeting location will be in the overnight backpackers lot 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)
Travel Watercolor Kit for Each Guest
Guided Watercolor Painting Session
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.
Personal Watercolor Supplies (Optional as a travel kit is provided)

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.

Do I need prior painting or art experience?

Not at all. This watercolor session is guided, approachable, and designed for complete beginners. The goal is to slow down, engage creatively with the natural environment, and enjoy the process — not to produce a technically perfect painting. The instructor will offer light guidance and painting styles to try, but there are no expectations and no wrong answers. Guests with prior watercolor experience are welcome to explore at their own level.

What art supplies are provided?

A travel watercolor kit is included for every guest. This includes watercolor paints, a brush, and watercolor paper. You are welcome to bring your own supplies if you have materials you prefer — just keep weight in mind, as everything must be carried in your pack.

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.