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
Indian Summer's guides clearly know how to make riders feel safe and comfortable, which comes through repeatedly in reviews. Ashton, Kathy, and Devon get called out by name for their patience, knowledge, and genuine care for both horses and guests. Several nervous riders mention conquering fears here, including one person who hadn't been on a horse in 13 years after being bucked off. The guides match horses thoughtfully to experience levels and take time answering questions, snapping photos, and adjusting to each rider's comfort zone. The Virginia vineyard settings at places like Veritas, Trump Albemarle, and Pollack deliver stunning backdrop rides that aren't the typical nose-to-tail trail experience. Groups with mixed experience levels do well here, and the horses like Gracie, JayJay, and Bo consistently get praise for being gentle and well-mannered. One cautionary note: there's a single incident where a guest experienced multiple spooking episodes with their horse and chose to cut the ride short due to safety concerns. This appears to be an isolated case among overwhelmingly positive experiences, but it's worth noting if you're particularly nervous about riding. Overall, this operation seems to strike the right balance between scenic adventure and attentive guidance.
The mid-March ride we had at the Veritas Vineyard was incredibly picturesque, almost as though we were in a Thomas Kinkade painting. Being amongst the Blue Ridge mountains, the weather changed up on us last minute. Ashton, the owner, had clear and direct communication about timing & rebooking (due to potential inclement weather) up until the scheduled timeslot. Ashton & Riley were professional, knowledgeable, and well versed. They ensured that we had the most comfortable and risk-free ride possible. 5 stars no questions about it! ⭐️⭐️⭐️⭐️⭐️ We had a beautiful ride filled with pleasant conversation & laughs. After the ride we enjoyed a delicious wine tasting at Veritas Vineyard. Absolutely cannot wait for another ride with Indian Summer Guide Service!
Veronica Torrez
March 12, 2026
The mid-March ride we had at the Veritas Vineyard was incredibly picturesque, almost as though we were in a Thomas Kinkade painting. Being amongst the Blue Ridge mountains, the weather changed up on us last minute. Ashton, the owner, had clear and direct communication about timing & rebooking (due to potential inclement weather) up until the scheduled timeslot. Ashton & Riley were professional, knowledgeable, and well versed. They ensured that we had the most comfortable and risk-free ride possible. 5 stars no questions about it! ⭐️⭐️⭐️⭐️⭐️ We had a beautiful ride filled with pleasant conversation & laughs. After the ride we enjoyed a delicious wine tasting at Veritas Vineyard. Absolutely cannot wait for another ride with Indian Summer Guide Service!
Veronica Torrez
March 12, 2026