Trail Rides

Keswick Vineyards

  • 1575 Keswick Winery Dr. Keswick, Va 22947
  • Daily, 10:00-5:00 pm
  • Duration: 1.5 hours
  • Rate: $175/per person
  • Rider Minimum: 2
  • 434-244-3341
  • Offerings: Glasses, bottles, and flights
  • Reservations: No
  • Curbside Pickup: No
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About this Ride

Experience Charlottesville’s wine country like never before—on horseback! Indian Summer Guide Service offers private, guided horseback rides through some of the most breathtaking farms and vineyards in the region.

A Scenic & Historic Journey

Nestled in a valley of rolling farmland and surrounded by the Blue Ridge Mountains, this ride takes you through lush vineyards, past a historic estate home, and ends at a rustic tasting room.

What’s Included:

  • Private guided horseback ride through a stunning vineyard
  • Exclusive access to one of Charlottesville’s finest wineries
  • Post-ride wine tasting (optional, but highly recommended!)
  • All safety equipment provided – no experience necessary

Soak in the serene landscapes, rich history, and award-winning wines on this unforgettable ride. Book your Keswick Vineyards Trail Ride today!

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: 27 minutes

trail riders on horses riding through rows of vines
Two trail riders on horses standing in tall grass field
trail riders on horses riding through rows of vines
Two women on horses next to lake
Woman riding horse towards rows of vines
Woman riding horse on paved road
Two riders on horseback near new vineyard plants

Book Your Keswick Vineyards 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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