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Natural Awakenings Milwaukee Magazine

May 2026 Virginia Women's Hiking Retreat

Hiking with the wild ponies of the Appalachian Trail, biking the Virginia Creeper trail, and horseback riding in the stunning Grayson Highlands!

Retreat Dates: May 08, 2026, 3:00 PM – May 13, 2026, 9:00 AM

About the event Location: Damascus, Virginia

Activity Level: 3-4 (rated on a scale of 1-5)

Women of all ages welcome Max number of hikers per trip: 8 hikers, plus 2 experienced guides

Cost: $2,550 for a single occupancy room, $2,450 for a double occupancy room (pricing is for registration before 12/31/25, all after 1/1/26 pricing increases $100).

$200 non-refundable down payment due at sign up to secure your spot.

We’ll hike approximately 7-10 miles during the day, yet come home to a hot shower, a delicious dinner, and your own comfy bed. No camping required…after all, this is Glam-packing! Simply live in the moment on your vacation--we take care of all the meals, lodging, logistics, safety, and FUN!

While on your trip, you’ll hike, bike, and horseback ride! Hike with the iconic ponies of the Appalachian trail and learn the history of the area as you ride horseback through sweeping vistas. In addition to biking the Virginia Creeper Trail, you’ll eat at local restaurants and have the opportunity to shop in local stores.  

Price includes (vacation rental), meals (and snacks), daily transportation to and from the trailhead, biking, horseback riding, and endless adventure in a safe and supportive setting (with two Wilderness First Responder certified guides).  

To reserve your spot before they're gone, email: [email protected]

Date & Time

May 8, 2026

3:00PM

Location

The Appalachian Trail, Virginia - 829 Grayson Highland Lane, Mouth of Wilson, VA, 24363 829 Grayson Highland Lane Mouth of Wilson 24363 VA US

Get Directions

Participating Businesses

Trail Dog & Company