Experience the beauty and serenity of the Virginia countryside from a new perspective with private, guided horseback rides. From trail rides to winery tours, horse and wine enthusiasts alike can enjoy combining the adventures of wine tasting and horseback riding. Visitors can choose from multiple guide services offering horseback rides, wine tastings and private tours of the commonwealth, even for those seeking a location for business retreats and corporate events. There are plenty of options for touring and tasting on horseback. From award-winning wineries, breweries and cideries, there is something for everyone to enjoy on a private horseback tour of Virginia Wine Country.

Image @ Aaron Watson Photography for Wine & Country Life

A Winery Experience for Horse Lovers

A leisure ride around local vineyards and trails is exactly what Albemarle county native Ashton Beebe intended when he started Indian Summer Guide Service in 2010. For Beebe, growing up exploring the area on horseback only influenced his appreciation and love of the land and animals that call it home.

vineyard horse tours
Image @ Aaron Watson Photography for Wine & Country Life

I’ve loved horses ever since I can remember,” he says. “I would dream of, one day, becoming a cowboy or wrangler. Every birthday and Christmas, I would ask for a horse. My parents recognized my passion but had no knowledge of horses, so they decided the best option was to put me in lessons.”

Starting a Family Business

“He [Lamb] taught me how to engage horses in a gentle manner from the ground up, working in a round pen to becoming a safe and knowledgeable wrangler. Feeling the connection and teamwork while sitting on a horse is second to none,” Beebe says.

“I decided to start ISGS (Indian Summer Guide Service) after traveling around working as a wrangler and guide. I paid attention to how every operation was run—not just the business aspect, but the care of the horses, tack and other equipment it takes to run it.”

“He [Lamb] taught me how to engage horses in a gentle manner from the ground up, working in a round pen to becoming a safe and knowledgeable wrangler. Feeling the connection and teamwork while sitting on a horse is second to none,” Beebe says.

“I decided to start ISGS (Indian Summer Guide Service) after traveling around working as a wrangler and guide. I paid attention to how every operation was run—not just the business aspect, but the care of the horses, tack and other equipment it takes to run it.”

Blending Horseback Riding and Wine Tasting

But it wasn’t enough to serve the community with just any riding service. For Beebe, he wanted to do something no one else had done before. “My wife, Mary, also a small business owner, had previously worked in the tasting room at Pollak Vineyards,” he said.

“We soon began offering rides there and quickly expanded to King Family Vineyards, Veritas Vineyard & Winery and also Castle Hill Cidery” Like the vineyards where they ride, the ISGS is also family-owned and operated with currently 20+ horses. “It just took those first few families to believe in us and give us a chance and for that we’ll be forever grateful.”

vineyard horse tours
Image @ Aaron Watson Photography for Wine & Country Life

The ISGS offers vineyard rides at four award-winning vineyards across Virginia Wine Country. Whether you’re an equestrian or wine enthusiast, guided horseback tours offer a breathtaking adventure. Each tour lasts about an hour or an hour and a half depending upon the vineyard and is led by one of ISGS’s sophisticated guides.

After the ride, indulge in a wine tasting and stock up on your favorite wines back at the vineyard. ISGS also offers brewery rides at Charlottesville’s award-winning Devils Backbone Brewery and Albemarle Ciderworks. Enjoy mountain views followed by a delicious cider flight and tasty eats from the tasting room.

Exploring the Virginia Countryside on Horseback

“It’s a humbling feeling … being a part of nature’s solitude,” Beebe says. “The feeling is irreplaceable. You just feel so alive saddled atop a beautiful creature freely exploring the corners of our region you wouldn’t otherwise get to see.”

Currently, adventurers can choose from a variety of different tours and properties that include wineries, a historic property and cideries. On horseback, “you get to take in beautiful views that can’t be seen from the tasting rooms. We’ll point out landmarks and points of interest that can be seen on the rides.”

On horseback, “you get to take in beautiful views that can’t be seen from the tasting rooms. We’ll point out landmarks and points of interest…”

“Anywhere from two to five hours, we’re unplugged and ‘getting lost’ in the mountains,” Beebe says. “Steep, sometimes rocky, terrain, water crossings and wildlife sightings really make each ride an adventure and an experience you’ll be talking about forever.” 

Image @ Aaron Watson Photography for Wine & Country Life

For riders looking to truly experience Virginia’s countryside, ISGS offers back country rides through the commonwealth’s stunning Blue Ridge Mountains. These rides last about three hours and take riders through creek crossings, steep terrains and rocky trails. Relish in the beauty of the commonwealth’s wildlife and enjoy a boxed lunch while surrounded by breathtaking views. While the ride does not stop at a vineyard, there are stunning vineyards nearby that riders can relax at following the tour.

What to Expect on a Vineyard Horseback Tour

While Beebe himself prefers riding in the late summer, ISGS offers tours throughout the year. Experience the gorgeous fall foliage of the autumn months, the natural solitude of the winter months or the blooming flora of the spring and summer months. 

Riders of any skill level are welcome to enjoy the benefits of private horseback riding and local beverage tastings. Horses are well trained and responsive, and guides are able to safely instruct all riders through an unforgettable experience.

Vineyard Horseback Tours offer the unique experience to enjoy both the solitude of the Virginia countryside and the leisure of award-winning wines or craft beverages in harmony with one another. The tours perfectly combine adventure and luxury together for the ultimate Virginia Wine Country experience. Horse enthusiasts can also enjoy polo at King Family Vineyards or attend one of Virginia Horse Country’s many equestrian events. Virginia Wine Country is the perfect place to experience rich hunt country culture.

SARAH SHORT has degrees in English and journalism and a master’s in HR, and her work can be seen in many of our publications on topics ranging from wine and weddings to parenting and sporting life.

With over 15 years of experience, AARON WATSON along with his wife Lisa and the wonderful AWP team enjoy photographing weddings, family portraits, senior portraits and commercial work in Charlottesville, Virginia and worldwide.




Virginia Wine & Country celebrates elevated living in Virginia Wine Country. Virginia Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The Virginia Wine & Country Gold Book is an annual guide to the top award-winning wines, wineries and experiences in Virginia Wine Country. The annual Virginia Wine & Country Wedding Planner is an art book of elegant Virginia weddings. Virginia Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media also provides branding, web design and PR services for the wine industry.