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  • Lowest Rate Guaranteed
  • Breakfast included
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  • Free off-street Parking
  • Free EV/Tesla Charger
  • Smoke-free Rooms
  • Only children 14 years and older
  • No pets
Three people riding towards the sunset down a trail in a field with the mountains in the background.

How to Saddle Up: Exploring the Best Trail Rides near Charlottesville VA

Virginia’s state motto has long been “Virginia is for lovers,” but that motto should also include “horse lovers.” As one of the top ten states for horse lovers, we want to share the best trail rides near Charlottesville, VA, along with another local equestrian pastime, the steeplechase. Whatever your level of riding experience, we can give you some great ideas that will let you check “trail ride” off your bucket list. This adventure is just one of many that you will find in the Charlottesville area.

Our Favorite Guided Trail Rides and Farms

Before you book your trail ride, think about your preferred riding environment. Do you want to ride in the forest or through a vineyard? Ensure you voice your desired experience to the stable so they can steer you to an appropriate ride. There are many choices for farms in the area; these are our favorites:

Indian Summer Guides

Indian Summer Guides have a variety of rides available, including vineyard, brewery, and back country. Imagine riding alongside the vines of award-winning grapes or the foot of Wintergreen Mountain through 100 acres near a brewpub.

There are many wineries to choose from, and after your ride, you can visit the tasting room and sample the fruits of the vines you have observed. It is a unique way to enjoy our local wineries! The winery and brewpub tours last between an hour and an hour and a half, depending on the location. The back country tour is three hours through the mountains, with an option for a boxed lunch. Plan on spending between $150 – $200 per person, plus tips for your guide, depending on the tour selected.

Rebels Run Afton Mountain

Rebels Run Afton Mountain is a horse lover’s dream! Visit this horse farm in the middle of both the Blue Ridge Mountains and wine country. Book a two or three-hour vineyard trail ride with a group, or arrange for a private ride.

Start off through the woods and over some creeks. Then ride through the actual vineyards, ending up at their tasting room. If you can handle it, take some time for a tasting (cost not included in your trail ride). Arrange in advance for a “Cowboy Charcuterie” picnic, and enjoy it along with the breathtaking views of the lake. Finish with the ride back to the farm. The cost ranges from $200 – $245 per person, depending on the length of the ride.

A Local Tradition: The Foxfield Races

Although you won’t be able to ride the horses at the Foxfield Races, these twice-a-year steeplechase races are a tradition not to be missed! The races occur on the last Saturday in April and the first Saturday in October. What is a steeplechase? The race requires the horse and rider to race a course between 2 and 4 miles long, jumping over obstacles, including fences, water jumps, or open ditches. The fences are a minimum of 4.5 feet high.

The Foxfield Races began in 1978; the location is a former airport and riding school. The course is 2.1 miles long. The spring race is a UVA tradition, so you will see many local college students, while the fall weekend has a more family focus. Come and enjoy the thrill of witnessing the combination of speed and raw power of these experienced horses.

Foxfield Inn: Your Charlottesville Haven

Exploring the best trail rides near Charlottesville is just one of the many activities you can find in our local area. We abound in history, natural beauty, and dozens of distinguished restaurants that satisfy any foodie. Relax in our well-appointed guest rooms. If you want to continue the equestrian theme, choose the Hunt Country Room with a king bed and fireplace. Book your stay now, and let us help you plan a memorable getaway.


Photo Credit: ©Jonathas Cardoso via

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