Trail Rides

Cunningham Creek Winery

About this Ride

Explore Charlottesville’s wine country on horseback with Indian Summer Guide Service. Our private, guided vineyard rides offer exclusive access to some of the region’s most breathtaking farms and wineries, making for a truly unforgettable experience.

A Ride Through Nature & Flavor

Your journey takes you through lush vineyards, along a peaceful creek, past blooming strawberry fields, and even by a playful goat pasture—all leading up to a relaxing wine tasting at a charming local winery.

What’s Included:

  • Private guided horseback ride through scenic farmland
  • Exclusive access to a premier Charlottesville winery
  • Post-ride wine tasting (optional, but a must-try!)
  • All safety equipment provided – no experience needed

Ride, relax, and raise a glass! Book your Cunningham Creek Winery Trail Ride today for an adventure filled with nature, wine, and unforgettable memories.

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: 35 minutes

Man and woman riding horses through field with yellow flowers

Book Your Cunningham Creek 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!