When Highlands was founded in 1875, there was no road to Whiteside Mountain. So in 1881 Samuel Kelsey began work on a wagon road that began at the north end of 5th Street and ended a quarter-mile from the top of Whiteside Mountain. Completed in 1883, the trail wound for 4½ miles through a forest lined with huge hemlocks. Photograph courtesy of Tammy Lowe.