The Forest Society purchased High Five with donated funds in 2004. It got its name when several members of the Forest Society's Land Management staff walked to the top and looked out at the expansive view. One of the staff members remarked that he just wanted to give a “high five," and the name stuck.

These lands had been in the Heald family for more than a century and are collectively known as the Heald Tract. They had historically been well managed by the Healds for multiple uses, including apple orchards, wildlife habitat, forest products, passive recreation, education, and flood control.

During the 1930s and 1940s, a substantial part of the northerly portion of Gap Mountain, Carboni Pasture, was owned by a cattle and horse dealer. It was purchased with other adjoining land by investors who eventually incorporated themselves into the Gap Mountain Company.