The legend of the Pine Tree Sitter dates back to 1952 when Ray Brinson, a local carpenter, constructed a wooden tree house in a pine tree to temporarily live in as a way to gain publicity for the festival. Brinson set a record by staying in the tree for 30 consecutive days, coming down on the morning of the festival. He later tried to break his record in 1953, but bad weather forced him down before reaching his goal.

Many local citizens took turns as the Pine Tree Sitter through the years, with a few notable records being set by Lee Studstill, who remained in the tree for 31 days in 1982 and then for 32 days in 1985; WXRS DJ Jeff Wiggins, who made it 33 days in the tree in 1986; and Bobby D, another WXRS DJ who currently holds the record at a whopping 47 days in the tree.

Of course, as times have changed, so has the structure that houses these Pine Tree Sitters in the tree. The tree house has evolved from a rough, sparsely furnished wooden structure in 1952, to a metal building today that features cable television, wireless Internet, an adjustable bed, restroom facilities, and a front porch with custom furniture that looks out over the beauty of downtown Swainsboro. The location has also changed, from the Courthouse Square, to just across the street to where the Pine Tree Sitter now resides at The Boneyard.

Though many of the amenities within the tree house have changed throughout the years, a few things have remained constant, including the milk crate and pulley system that is used for hoisting meals and supplies to the Pine Tree Sitter and the generosity of local businesses and restaurants in feeding and supplying the sitters.

Perhaps the most prominent change is the rotation of the Pine Tree Sitters. Though in the past one sitter would stay in the tree for 30 days or longer each year, modern day sitters rotate daily, with a new local celebrity or business owner taking the perch every 24 hours.

The sitters are featured on area radio stations during their time in the tree and often toss treats, which may range from candy to t-shirts to gift certificates, down to visitors. The Pine Tree Sitter may be visited in the weeks preceding the Annual Pine Tree Festival, often beginning in early April.