Watercolors + Backpacking

GRAYSON HIGHLANDS, VA

Watercolors + Backpacking

Grayson Highlands, VA

2 days

1 night

up to 6 miles

Roundtrip

7 Guests

MAXIMUM

$375

Join us on a backpacking trip filled with beautiful views and time to paint

Spend a weekend slowing down and soaking in the beauty of Grayson Highlands on this 2-day, 1-night backpacking and beginner watercolor experience. Designed with approachable mileage in mind, we’ll hike a short distance to camp before settling in for an afternoon of guided watercolor painting surrounded by mountain views, open highlands, and fresh air. All art supplies are provided and guests will leave with artwork and a watercolor kit to take on their future travels.

Whether you’re new to backpacking, watercolor, or both, this trip is designed to be relaxed, welcoming, and beginner-friendly. Learn backcountry basics, enjoy time outdoors, and leave with new skills, new memories, and your own trail-inspired artwork to take home.

testimonials from women like you!

The best experience

"Had the best time on my first backpacking trip. Liza is a great leader, watched out for our safety, supplied tons of supplies, taught us how to filter water, set up camp, went our pace climbing the mountain. Can’t wait to do a 2 day and 2 night trip. I definitely recommend Happy Hiking Co.!"

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Truly Amazing

"It was so awesome. This was my first time backpacking and I can hardly wait to go again. Our guide was absolutely fantastic, she explained everything, and was so supportive. She gave us many options along the way based on how we felt. All of the gear and food that was provided was great. There are no words or pictures that fully describe the views and the sunrises that we saw. It was a trip that I will never forget. Thank you Happy Hiking Company."

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Experienced guide with great gear and stories!

"Liza was a superb guide. This was a trip for beginners to experience a single overnight backpack tent camping trip. She had thoughtfully arranged all the gear, we brought our own personal items. The gear was in excellent condition. As a conscientious leader, she checked in with us individually about how we were faring and adjusted as needed. Liza was very familiar with the trail and history which made the trip more enjoyable. And we got to see the wild ponies"

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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 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

Slow down and experience Grayson Highlands in a different way. This trip combines beginner-friendly backpacking with a relaxed afternoon of watercolor painting, giving you time to enjoy the views rather than rushing through the miles. Set up camp, settle into the rhythm of life outdoors, and create something inspired by the landscape around you.

Expect mountain views, open highland meadows, fresh air, and a supportive small-group experience. Whether you come to build backpacking skills, try watercolor for the first time, or simply unplug for a weekend outside, you’ll leave with new memories and a deeper connection to the trail.

What awaits you...

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.