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Upperville Trail Ride

  • Upperville Colt and Horse Show 8300 John S Mosby Highway Upperville, VA, 20184 United States (map)

In June 1863, the Civil War raged along the Ashby’s Gap Turnpike. A week of intense cavalry battles culminated on June 21 with the Battle of Upperville. Follow in the footsteps of the action during our Battle of Upperville Trailride! Historian Daniel Murphy will guide us along some of the most intense action of the day as we ride the route of the Union army as they advanced towards Upperville 157 years ago.

The ride begins at the Upperville Colt and Horse Show grounds, before moving westward, past historic Green Garden and Kincheloe’s Mill, and to Trappe Road. Please arrive early as the ride will begin at 9:00 AM and last approximately 2 hours. Participants are responsible for providing their own horse and riding equipment. Protective hard helmets are required by our insurance. They should also be comfortable walking, trotting, crossing small creeks, and riding on hills. If you need to hire a horse, please let us know and we can make local recommendations.

Water and snacks will be provided. You are encouraged to bring your own tailgate lunch. All riders must provide Coggins Papers upon arrival.

Upperville Trail Ride
from $40.00
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History on Tap: Harpers Ferry off the Rails

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August 7

Drive-Thru History: Virginia Doughboys and the Great War