Ride a private guided trail through Keswick Vineyards, then enjoy a complimentary glass
1.5 Hours
Private guided ride, 1 glass
Saddle up for a private, guided horseback ride at Keswick Vineyards, led at a walking pace. Explore wooded trails and vineyard views, then head back to the tasting room afterward.
Minimum of 2 customers is required to run this ride. Ages 12+; riders under 12 must have some riding experience. Closed-toe shoes and pants are required; helmets are available but not required.
Cancel 7+ days before for a 90% refund (booking fees non-refundable). Cancel 48+ hours before for a gift card. Full refund or gift card if the operator cancels due to weather or other unforeseen circumstances. No-shows or cancellations under 48 hours are charged full price.
Yes. You need at least 2 customers for the ride to run. If there aren’t enough riders, the operator will reach out to reschedule.
Wear closed-toe shoes and pants.
No. Helmets are available but not required.
Keswick Vineyards
Ashton and his team have built something genuinely special here, pairing horseback riding with some of Virginia's most scenic vineyard settings. Rides take place at locations like Veritas, Merrie Mill, and Pollack Vineyards, weaving through fields, forests, and wine country with views that reviewers consistently describe as breathtaking. The guides are a clear standout, patient and knowledgeable with beginners while keeping things relaxed and fun for more experienced riders. What comes through repeatedly is how well the team handles nervous or first-time riders. Multiple people mention conquering fears or being surprised by how comfortable they felt, which says a lot about the tone Ashton and his guides set. The horses themselves get high marks too, described as gentle, well-mannered, and obviously well cared for. Groups ranging from bachelorette parties to family outings all seem to leave happy, and many mention already planning a return visit.
Had a tremendous experience, our guide was extremely knowledgeable and a great time to be around. Couldn’t recommend Indian Summer Guide Service enough!
Stopel drewsky
May 5, 2026
Had a tremendous experience, our guide was extremely knowledgeable and a great time to be around. Couldn’t recommend Indian Summer Guide Service enough!
Stopel drewsky
May 5, 2026