After college, Way ran a farm and became involved in several Vermont businesses, including the Green Mountain Mutual Fire Insurance Co. in Montpelier, the Fli-Rite School of Aviation in Swanton, and his father’s business, the Porter Screen Company, in Burlington. In 1944, Way purchased an inn in Middlebury, Vt. and renamed it the Waybury Inn; the inn was later used as a location for exterior shots for the television show Newhart. Way and his wife, Marjorie Holbrook Scott (m. 1928) were living in Middlebury at the time of Way’s death on October 4, 1973.

Topics in Way’s diaries include the 1918-1919 influenza pandemic, fraternities at the University of Vermont, Kake Walk, World War One and UVM’s SATC program, Vermont farm life, and male friendships and relationships in the early twentieth century.