Trail Rides

Chiswell Farm & Winery

  • 430 Greenwood Rd., Greenwood, VA 22943
  • Wed-Sun: 11:00-6:00 pm (seasonal hours, check website)
  • Duration: 1 hour
  • Rate: $150/per person
  • Rider Minimum: 2
  • 434-252-2947
  • Offerings: Glasses, bottles, and flights
  • Reservations: No
  • Curbside Pickup: No
Website

About this Ride

A household name in Albemarle County, the Chiles family has been farming and cultivating orchards for over 100 years. At Chiswell Farm & Winery, history and hospitality come together in a beautifully restored 1920s estate, now open for guests to enjoy award-winning wines and seasonal light fare in a warm, inviting setting.

A Historic & Cozy Retreat

  • Explore historically themed rooms, each designed for lounging and relaxation
  • Savor seasonally inspired, in-house fare, featuring fresh Chiles-grown ingredients
  • Enjoy an elegant yet welcoming atmosphere, perfect for wine lovers aged 21+

Part of the Chiles Family Tradition

Chiswell Farm & Winery is part of the Chiles family of venues, which also includes:

  • Chiles Peach Orchard
  • Carter Mountain Orchard
  • Spring Valley Orchard

Each offers family-friendly experiences, including Pick-Your-Own seasonal fruits. (Please note: Outside food is not permitted.)

Plan your visit to Chiswell Farm & Winery—where rich history, stunning landscapes, and exceptional wines come together for a truly memorable experience.

Rules, Guidelines, & Suggestions

  • Alcoholic beverages and smoking are not permitted on any of our rides
  • For the safety of all riders and horses, we do not allow you to bring your own horse
  • Helmets are available but not required
  • Closed toed shoes and pants are required
  • Our guides are are working long before your ride begins and long after it ends. They do their best to provide you with an unbeatable experience. If you had a great time on your ride, please show your appreciation by tipping your guide.
  • All of our rides are at a walking pace, regardless of experience

Nearby

UVA: 20 minutes

Two men riding through open field
Two men riding through open field with horse's head and neck in foreground

Book Your Chiswell Farm & Winery Trail Ride

Don’t miss out on this unforgettable Blue Ridge experience. Secure your spot today and enjoy the perfect blend of adventure, relaxation, and local flavor!

Testimonials

“Had a great ride, Ashton was fantastic! The ride was a birthday present for my wife and she loved every second of it. I prefer things with an off switch but these horses are great. They went where they were told and even made me want to go again. If you’ve ever wanted to ride and been a little apprehensive about it then this is the only way to go.”

“Our ride in the mountains was a blast!!! The horses were sound and instructor was knowledgeable and eager to answer questions. I can no longer think of a better way to explore nature than to ride a horse. I can’t wait to go again.”

“If you are looking for a FUN venue here in the C’ville area, this is it!! Ashton was the perfect guide. Preddy Creek Trail was an easy ride and the horses were very well behaved. Ashton had the best horse for each one of us and they are beautiful quarter horses! Can’t wait to try another trail, thank you Ashton, you ROCK!!”

“Ashton is so knowledgeable and patient. There lots of ways to customize your experience from riding ability to location. I can’t wait to go out again.”

“I’ve been on a lot of trail rides, mostly with nose-to-butt horses that are great for people with no experience riding, but riding Ashton’s horses is not like being on a merry-go-round. The horses are great and actually let you lead.  Ashton is a first class guide with incredible personality.  Definitely will be back, hopefully for a longer ride.  If Ashton’s dog Mo is present you are in for a treat if you love dogs.  Nothing better than a trained border collie to play with as a bonus!!!  Thanks for a great time and we look forward to our next ride!”

“This is a must do if you are in the area!! Totally worth it!! Ashton is a great guide and super nice! 5 stars all the way!”

Read Our Google Reviews
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Founded in 2010 by Ashton Beebe, Indian Summer Guide Service offers private, guided horseback rides through the scenic landscapes of Central Virginia.

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