Wilson was the son of William Calfee and Nancy Davis. He married Jane Peery Bailey.

The following is from the diary of W.O. Hollandsworth, pioneer settler of Pinecrest Camp, near Prosperity, Raleigh Co., WV:
"In the fall of 1836, I, in the company with Stephen Saunders and Wilson Calfee, left Pulaski County, Virginia, for the wilderness. After five days travel through the unbroken forest, we came to the home of Thomas Warden near Cranberry Branch [which is now in Raleigh Co., WV]. We hunted and visited his neighbors, Jno. Williams, Sparrel Bailey, Jno. Bailey, Alfred Beckley, at Wildwood. The next nearest settlement was on Coal River (They bought land except...) Wilson Calfee had enough of the wilderness and would not buy any land."
Wilson returned to Mercer Co., WV, where his brothers Samuel and James were living.
Wilson built his first home at the Gap of Stony Ridge, now occupied by the Mercer Mall (Bluefield) in 1845. Later, he built a new log home a mile or so eastward. Wilson was a full-time farmer but also taught at the Gap Elementary School for three to four years for no salary. One winter, he taught for four months at $25 per month. His name is on a Mercer County, WV teachers list in 1872. Wilson got his mail by riding to Bethel where Elijah "Lige" Bailey had a store. Wilson was an elder in the Disciples of Christ congregation. "Left-handed and unprepossessing in appearance, he was very enterprising." His farm extended from Mercer Mall to Monte Vista Cemetery and west to the Mercer County airport. He was also called "Uncle Willie" by some. He died of "grip."

Calfee Memorial Christian Church, Bluefield, WV, dedicated in 1904, was named after Wilson and his brother Rev. James Calfee.