The trail begins at the parking lot near the old Whitely Farms. This single-track loop trail rambles through hayfields and a forest of mature hardwoods over a packed earth surface. The grade is moderate throughout, with a rapid descent near the approach of the Hopkins Road crossing and the connector to the David English Trail. The Whitely Farms Trail can also be accessed by a connector trail near the Smith Mill Road Parking Area. A double-track cut-off trail runs downhill parallel to a small creek from Possum Hill to Hopkins Road.
