5. Shepherdstown, WV to Mt. Holly Springs, PA

SHEPHERDSTOWN, WV TO MT. HOLLY SPRINGS, PA – 119 miles

Most of the roads you’ll ride in this section are paved and allow for ample time to visit Harpers Ferry, WV. A significant Union army camp, headquarters site, and logistical supply base during the Civil War, it also served as the largest surrender point of Confederate forces at that time.

The town lies at the confluence of the Potomac and Shenandoah rivers, the meeting point of Maryland, Virginia and West Virginia. After you hop back on the bike, you’ll soon hit South Mountain Creamery, a worthwhile stop with wholesome and tasty food fresh from the Amish working farm located there. The remaining part of your day will be accentuated by a backdrop that morphs from thick groves of deciduous conifers to wide open rolling fields with bucolic small farms and sprawling cattle ranches.

The canopy tightens once more upon entering Michaux State Forest, and the road regains a speedy, yet super flowy two-track. The town of Mt. Holly Springs lies at the end of this segment.

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