[2] A third segment runs north from US 65 in Damascus to Highway 92 at Rabbit Ridge in Van Buren County.

[4] Highway 285 winds east through a sparsely populated area of the county before terminating at Woolly Hollow Road, which serves as the entrance to Woolly Hollow State Park.

[2] The roadway continues east as Blythe Road under county maintenance.

[2] Highway 285 begins in southern Van Buren County at US 65 in Damascus.

The route runs west past the Damascus Gymnasium and Melvin Chrisco House, both listed on the NRHP, before exiting the corporate limits.