Ride Chiswell Farm trails, then head to the tasting room
1 Hour
4 people
Private guided ride, 1 wine glass
Saddle up for a private, guided horseback ride at Chiswell Farm & Winery, then wrap up back at the tasting room for light fare and wine.
Ages 21+ only. Minimum of 4 customers is required to run the ride. Closed-toed shoes and pants are required.
Gratuity is customary; standard tip is 20%.
Cancel 7+ days before for a 90% refund (booking fees non-refundable). Cancel 48+ hrs before for a 90% refund (booking fees non-refundable). No-shows or cancellations within 48 hrs are charged full price. Full refund available if operator cancels due to weather or unforeseen circumstances.
You need a minimum of 4 customers for the ride to run. If that minimum isn’t met, you’ll be contacted to reschedule.
Wear closed-toed shoes and pants.
No. Helmets are available but not required.
Chiswell Farm & Winery
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