The high plateau on which Highlands stands remained remote during the early days of Macon County’s history. Samuel Truman Kelsey and Clinton Carter Hutchinson of Reno County, Kansas selected the plateau for the development of a new town. They arrived at the site of their new town on February 1875, purchased 839 acres and began development and promotion of the area. It was to be called Kelsey’s Plateau but the name was soon changed to Highlands.

Joseph Halleck built Highlands Inn in 1880 as the first hotel in Highlands, known as Highlands House. In 1883 Joseph Fitts bought the inn and was running it when the Moccasin War took place in 1885. In 1886 John Jay and Mary Chapin Smith were the recipients of the Inn, a wedding present, from Mary Chapin’s aunt, Eliza Wheaton. During this era, the Inn was known as the Highlands House and fondly referred to as Smith House.

One of the earliest photographs of the Inn shows bewildered guests gazing over the dusty, earthen Main Street as a group of elephants calmly walked by. It was all part of a visiting circus that somehow made it up the mountain trail. Also, included in all known photographs of the inn is the Maple tree on the corner of 4th & Main Street. This tree is known to Highlanders as the “Signal” tree as it is the first tree to begin the fall color.