Rolling Hills 2-Hour Riding Package in Dubois, IN — Challenging 300-Acre Trail Ride

On the rim of Dubois County’s farmland, Rolling Hills offers a two-hour ride that puts seasoned trail riders on 300 acres of real terrain. Located at 5814 N 735E, Dubois, IN 47527-9670, this is not a lesson—it's a workout for you and your mount. The property pushes through open grazing ridgelines, oak–hickory woodlots, shallow limestone outcrops and narrow creek-bottom trails that demand steady hands and confident seat. Expect sustained canters on grassy knolls, technical descents between fence lines, and a few water crossings that test a horse’s surefootedness. Guides run small groups—maximum four riders—so the pace stays challenging and the experience feels bespoke. Riders must have at least ten hours of prior trail time and be twelve years or older, which keeps the ride moving and safe. If you need last-minute questions, you can call Shellie at 930-333-7651. Note: all bookings use Eastern Time. The route reveals local geology: the underfoot changes from fertile loam to thin, cherty limestone that shapes the subtle knobs and hollows that make this landscape interesting. Wildlife sightings are common—white-tailed deer slip through the edge habitat and red-tailed hawks patrol the ridges—so bring a steady hand for unexpected stops. Because the ranch is private, access here feels more remote than a public park ride, and you’ll cover terrain most visitors never see. Logistics are straightforward: two hours in the saddle means a solid cardiovascular stint—expect to trot and canter more than idle. Helmets and proper boots are recommended; bring layered clothing, water, and closed-toe shoes. The outfit enforces a 24-hour cancellation policy with rescheduling possible, so plan accordingly. For riders visiting southern Indiana from farther afield, a stay in nearby Jasper or Ferdinand leaves you well placed to combine this ride with river kayaking, limestone cave visits, or local dining. Rolling Hills stands out because it’s private acreage run for riders who want a demanding, honest trail rather than a slow scenic loop. The combination of varied hills, rock ledges, creek crossings and tight single-track makes it a top choice for experienced riders exploring Indiana’s lesser-seen backcountry. Bookings are limited to four riders per departure, keeping trails uncluttered and allowing guides to tailor pace and lines to rider ability. Minimum age is 12 and participants should carry proof of riding experience (10+ hours recommended). Check-in at Dubois (Rolling Hills) Location — 5814 N 735E Dubois, IN 47527-9670. The operator enforces a 24-hour no-refund window but will allow rescheduling; call Shellie at 930-333-7651 for details.