Women's Hiking Retreat - Damascus, VA (May 8-13, 2026)

Early Bird Discount!  Pay in Full by December 31 and save $100!

(Discount applied at checkout)

Trip Highlights:

Price:

The cost for this trip is $2750 per person for a private room or $2650 for a shared room, which includes a non-refundable deposit of $200.  The deposit is due at the time of booking to secure your spot, and the remainder will be due 90 days before the start of the trip.  You are welcome to pay the full amount at the time of booking, or pay the deposit now and the rest later.  

Difficulty Level: Beginner / Novice

This Beginner/Novice hiking trip is considered Moderately Strenuous.  A moderately strenuous hike is considered to be generally challenging for an unconditioned person.  It is suitable for those with some hiking experience on a mix of terrain and elevation gain and loss.  While this trip is great for first time backpackers, you should be comfortable hiking at least 6-10 miles with a weighted day pack on varying terrain.

Daily mileage on this trip ranges from 5 miles to 10 miles, with up to 1,500' of elevation gain.  The terrain on this route is very rocky and rooty, so you should be comfortable hiking on uneven terrain and have good traction on your shoes.  There are some steep inclines and large rock steps, as well as a few log bridge creek crossings. 

While we will not be backpacking on this trip, you will be expected to carry your own daypack with snacks and water during the day hikes.  You will receive a detailed packing list after booking, and your guide will discuss what to bring (and what not to bring) during your virtual orientation.

What's Included:

• Vacation Rental (single occupancy rooms)
• Meals (breakfast, lunch, dinner at AirBnB) and hiking snacks
  
• Shuttles to and from trailheads
• Bike rentals for the Virginia Creeper Trail
• Guided horseback riding
• Virtual Orientation and Q&A session with your guide before the trip
• Expect advice, tips, and planning from two experienced and Wilderness First Responder certified hiking guides

Not Included:

• Guide gratuity (recommended 15-20% of trip cost)
• Lodging before/after trip
  
• Transportation to and from airports
  
• Personal items such as clothing, water bottles, and medications

What to Bring:

Your guide will provide you with a detailed gear checklist before your trip that’s tailored to your trip location and expected weather.  You’ll be expected to bring your own personal items such as clothing, footwear, and medications.  You will also have the opportunity to ask specific gear questions during your Pre-Hike Virtual Orientation with your guide.

Meeting Location and Itinerary:

You will be meeting your guides at your vacation rental in downtown Damascus, VA, a charming mountain town known as “Trail Town USA.”  The exact location of the vacation rental will be shared after booking.

We will plan to meet at 3 pm on the first day and depart at 8 am on the final day of the trip. The nearest airport is Tri-Cities Regional Airport (TRI) in Blountville, TN, about a 1-hour drive from Damascus.  Please make your travel arrangements accordingly.  

Sample Itinerary:

Day 1: Meet + Greet, begins at 3:00 pm

Days 2-5: Day hiking on the Appalachian Trail and Grayson Highlands, biking on the Virginia Creeper Trail, and horseback riding in the Mount Rogers National Recreation Area.

Day 6: Wrap-up + Departure, ends at 8:00 am

Your exact itinerary, routes, and mileage will be shared after booking, and may vary depending on weather, trail conditions, and group pacing. 

Group Size:

This trip is limited to 8 hikers.  In order for the trip to run as planned, we will require a minimum of 5 hikers.  If the trip minimum is not met, your guides will contact you 30 days before the trip with options to re-book or cancel. 

Travel Insurance:

• We highly recommend that you purchase travel insurance with appropriate coverage.  Travel insurance may be used to reimburse the cost of an unexpected trip cancellation, for reasons such as illness, injury, a death in the family, or travel delays.  Wildwood Hiking Company does not offer travel insurance, but you can search online for a provider that fits your needs.

Cancellation Policy:

We have a special cancellation policy for this trip, as it is a unique partnership with Trail Dog & Company.  Please read carefully:

If you cancel your trip 120+ days out from the trip start date, you receive a full refund (minus your non-refundable deposit).

Trip cancellations 90-119 days out from trip start date will receive a 50% refund (minus your non-refundable deposit).

If you cancel your trip within 90 days of the trip start date, you pay 100% of the trip cost, no refund including your down payment.