Ashley Wakefield Ramsdell was born on November 6, 1894 in Ocala, Florida. He attended Hillsborough High School in Tampa, class of 1913. Future Gator teammate Rex Farrior also attended. As an end on the football team, Ramsdell dropped a pass to tie the state championship game. The basketball team however did win a state title. Ramsdell is in the school's hall of fame.
Ramsdell attended the University of Florida in Gainesville, Florida, where he played several sports for the Florida Gators. Ramsdell was the starting quarterback for two seasons on the football team, a centerfielder on the baseball team, and a member of Florida's first basketball squad.
Ramsdell began his collegiate athletic career on Florida's freshman football team, when he was taught the quarterback position by coach and former Gator quarterback Bob Shackleford. Then he played for coaches George E. Pyle and C. J. McCoy on the varsity Florida Gators football team from 1913 to 1915. The highlight of his football career was a 60-yard touchdown run in the rain to defeat Tulane in 1915. Ramsdell also scored four touchdowns in the game with Mercer that year.
While running the bases during a baseball game against Auburn in 1915, Ramsdell accidentally stepped on the foot of first baseman George Steed and got his spikes caught in Steed's laces, which resulted in Ramsdell breaking his left leg with "a loud cracking noise". The serious injury ended Ramsdell's collegiate athletic career. Without their projected starting quarterback, the Gator football team went 0–5 and did not score a touchdown during the subsequent 1916 season.
Ramsdell married Geneva E. Mosley on June 2, 1917. Their daughter Jean was a Tampa philanthropist. Ramsdell's First World War registration says he is a schoolteacher in Tampa. He later settled in Plant City and owned a trucking company. After a stroke in 1950, he sold the business.