New Offering!

Join fellow adventurers for an EqWine Social—
a vineyard horseback ridewith wine, charcuterie, and great company.

Indian Summer Guide Service

Horseback Riding in Charlottesville, VA

Vineyards | Breweries | Private Estates | Backcountry

Are you ready for an adventurous trail ride in Virginia?

Choose your experience to start planning!

Gift Cards

Give them a horseback riding experience they'll remember!

“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!”

New Offering!

Indian Summer Guide Service

Horseback Riding in Charlottesville, VA

Vineyards | Breweries | Private Estates | Backcountry

Vineyard
Trail Rides

Brewery & Cidery Trail Rides

Backcountry Trail Rides

Are you ready for an adventurous trail ride in Virginia?

Choose your experience to start planning!

Veritas Vineyard & Winery

Pollak Vineyards

Merrie Mill Farm & Vineyard

Keswick Vineyards

EqWine Social at Merrie Mill Farm & Vineyard

Devil’s Backbone

Cunningham Creek Winery

Chiswell Farm & Winery

Albemarle Ciderworks

Gift Cards

Give them a horseback riding experience they'll remember!