THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Explore Virginia’s vineyard landscapes from horseback with guided tours at Cunningham Creek Winery near Charlottesville. This one-hour adventure blends serene trails and local wine tasting for a unique outdoor experience.
Explore Virginia’s vineyard landscapes from horseback with guided tours at Cunningham Creek Winery near Charlottesville. This one-hour adventure blends serene trails and local wine tasting for a unique outdoor experience.
Book with Indian Summer Guide Service
Verified experiences and guided adventures in the surrounding area.
Operated by Indian Summer Guide Service · Scottsville, Virginia
moderate.
1 hour.
Basic fitness level is sufficient; no prior horseback riding experience required but comfort with animals helps.
No prior experience is necessary; knowledgeable guides provide assistance and manage the pace to accommodate beginners.
Riders must be at least 12 years old to safely participate and meet the horse handling requirements.
Tours may be rescheduled or canceled in heavy rain to ensure safety and enjoyment.
A minimum of four participants is required to book a private horseback riding tour.
Yes, Cunningham Creek Winery offers onsite parking for guests.
Yes, each tour concludes with a wine tasting featuring selections from the winery’s local vintages.
Cunningham Creek Winery celebrates Virginia’s long-standing viticulture tradition dating back to the 19th century, contributing to the region’s agricultural heritage.
The winery practices sustainable farming techniques to protect soil health and local water sources, ensuring a low environmental footprint.
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.
Book with Indian Summer Guide Service