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Trail Rides

Come and share in the love of horses and experience riding through our engaging trail options with breathtaking scenery.

General Trail Ride

$95/Rider

Guests will get to learn the basic aspects of horsemanship, including grooming, tacking, and communication with the horses. They will then be led on a relaxing trail ride through the woods and get to enjoy the classic old-world scenery that northern Virginia has to offer. Down gravel roads, and through winding paths up the mountain ridge, guests may see for miles the sprawling farmland. They will encounter natural beauty from the streams of sunlight through the treetops to deer and even the great American bald eagle. If interested, guests will learn about the history of the land dating back as far as the civil war and how it shaped this part of the country and community in ways that are still reflected today.

Ice Cream Trail Ride

$125/Rider

Guests will start their experience by getting to know the horses and learning horsemanship through grooming and tacking up their horses. Guests will then be led on a lovely trail ride down backcountry roads that wind through the countryside. As we ride, guests will learn the history of Hillsboro and the Gap.


The trail will lead up to and through historic Hillsboro and the Old Stone School, where the local Moo Thru Ice Cream trailer is located. Guests will be able to dismount and order the ice cream of their choosing and relax, before saddling back up to head back to the farm. The Moo Thru offers a wide variety of handmade ice cream and toppings to create your own ice cream adventure. This trail is great for both children and adults to enjoy on warm days throughout the spring, summer, and fall. The price of ice cream is not included in the price of the trail, but ranges from $5+.

Vineyard Trail Ride:

$200/Rider

Guests will be able to combine two wonderful experiences into one with this unique opportunity. They will be able to engage in learning about all aspects of horsemanship and the local history of the town while riding shady trails on the mountainside. Guests will be able to ride at a pace in which they are comfortable, they are not merely limited to walking.

The trail will bring guests moseying through lush rows of a vineyard horseback. They will be able to get off and share in the lovely wine offerings from the vineyard's winery, Walsh Family Wines. Guests will be able to enjoy their choice of two glasses of their favorite wine or a tasting of a selection of wines. When guests book on Saturdays and Sundays throughout the summer season they will enjoy live music and events at the winery. Guests will be free to return to the winery after the conclusion of their ride.

OPTIONAL: Instead of a winery tour, ask about a brewery instead! Includes two glasses of beer per participant instead of a wine tasting.

Values for trail rides:
  • Horsemanship is where horse and rider meet in the middle to create understanding.

  • It is a privilege to be allowed to ride upon an animal, let alone one that could kill you without batting an eye, we ride with respect.

  • They know you, before you know you, be confident in yourself and them.

Rescheduling, Cancellation, and Refunds
  • Any ride may be rescheduled or cancelled with 48 hours notice, either by the guest or by DSS. The guest's deposit will be applied to the new ride or refunded as applicable. 

  • If a guest needs to cancel within 24hrs of their ride they will forfeit their deposit.

  • DSS reserves the right to cancel or reschedule within 2 hours due to weather concerns, or 45 minutes for severe weather concerns.