Adventure Brief
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.
2–3 hours
moderate
From $196.10
Family Friendly
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.
More ways to explore the area's outdoor wonders
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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.
Wildlife
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.
Indian Summer Guide Service
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.
Indian Summer Guide Service leads guided horseback rides across Charlottesville-area farms, vineyards, and ciderworks. Operating family-friendly and private experiences, the guide service pairs calm, well-trained horses with knowledgeable guides who prioritize safety, clear instruction, and an enjoyable pace for riders of varying experience.
The seasonal Santa's Chuckwagon in Roseland creates holiday memories: riders meet Santa, warm by a fire with hot cocoa, receive decorate-your-own cookie kits, and take professional photos beside gentle horses. Other public and private rides explore Merrie Mill Farm & Vineyard, Keswick, Chiswell Farm, Pollak Vineyards, Veritas Vineyard & Winery, Cunningham Creek Winery, and Albemarle Ciderworks, each finishing with a tasting or light fare at a rustic tasting room or family-owned winery.
Programs accommodate families, children, adults, and private groups; some rides require riders aged 12 and up while select vineyard rides are 21+. Routes traverse pasture, creekside paths, strawberry fields, and vineyard rows, offering Blue Ridge views and a relaxed countryside pace suited to beginners through experienced riders.
Indian Summer Guide Service focuses on curated, small-group outings that combine outdoor adventure with local flavors — wine flights, cider tastings, and intimate tasting-room experiences. Reservations are recommended for private vineyard or winery pairings and the popular holiday Santa's Chuckwagon. Contact information and booking details are available online; advance reservations help secure preferred dates and private experiences. All skill levels welcome.
Locations
Charlottesville & Roseland
Scenic farms, vineyards, ciderworks
Guided Rides
Knowledgeable guides
Safety-focused instruction on every trip
Scenic Routes
Farms & vineyards
Blue Ridge and countryside views
Tours Offered
9 experiences
From family to private rides
Reserve seasonal slots, private vineyard pairings, or the popular Santa's Chuckwagon for a memorable Charlottesville horseback experience.
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.
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
Sunscreen
Protect skin during longer exposure to sun on open trails.
summer