Horseback Riding & Wine Tasting Near Charlottesville, VA
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Suitable for riders with basic horseback riding experience; moderate fitness needed for controlling the horse over uneven terrain.
Overview
Saddle up for a unique horseback ride through Charlottesville’s scenic vineyards, topped off with an estate wine tasting. Discover rural Virginia’s charm from a fresh perspective.
Private Keswick Vineyards Ride
1.5 Hours • Open Daily
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Adventure Photos
About This Adventure
Experience the beauty of Charlottesville on a guided horseback ride through stunning vineyards and farms, led by knowledgeable guides. Enjoy breathtaking views of the Blue Ridge Mountains and finish your adventure with a delightful wine tasting at a rustic tasting room. A unique blend of nature and indulgence awaits!
Requirements
- Please note we need a minimum of 2 customers to conduct this ride. If for some reason we do not, we will be in touch to reschedule.
- For ages 12+, riders under 12 must have some riding experience
About
We provide guided horseback rides and tours to wineries and vineyards in the Charlottesville, Virginia area. Indian Summer Guide Service is fortunate enough to have access to some of the most breathtaking farms and vineyards in the region. Each of our private horseback rides is led by one of our knowledgeable guides, who will ensure your safety as well as your enjoyment. After the ride you can make your way to the winery to enjoy a wine tasting and stock up on your favorites. Nestled in a valley of rolling farmland and surrounded by the Blue Ridge Mountains, this ride will lead you through the beautiful vineyard, around the historic estate home and finish up at the rustic tasting room. We provide all safety equipment
What to Bring
- 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 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.
Adventure Tips
Book in advance
Private rides fill quickly, especially during harvest season—reserve your spot early.
Wear appropriate footwear
Sturdy closed-toe boots improve comfort and safety while riding through vineyards.
Bring a camera
Capture vineyard vistas and mountain backdrops along the ride.
Stay hydrated
Carry water to stay refreshed on warmer days during the horseback tour.
Local Insights
Wildlife
- White-tailed deer
- Red-tailed hawks
History
Keswick Vineyards sits in Virginia’s historic Piedmont, a region with agricultural traditions dating back to the 18th century.
Conservation
The vineyard employs sustainable farming practices to protect soil health and local habitats throughout the riding trails.
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Adventure Hotspots in Charlottesville
Frequently Asked Questions
Recommended Gear
Riding boots
Provides grip and protection when mounted.
Helmet
Safety first—helmets are recommended regardless of experience.
Layered clothing
Spring mornings can be cool; dress in layers for comfort.
spring specific
Sunscreen
Protect skin during longer exposure to sun on open trails.
summer specific