Wilbur “Web” Riley was the first class president at John Handley High School. He was a member of the Cadet Battalion, played both football and basketball, and was the Editor-in–Chief of the school’s newspaper “The Trail Blazer”.

He continued his education at Lynchburg College where he had a Hall of Fame career as the captain of the basketball team. He worked on the college’s newspaper and later married the daughter of the college president.

Following graduation in 1928, he was appointed assistant editor of the Woodstock Times, a semi-weekly newspaper in Woodstock, Virginia. He worked with the newspaper for three years before joining the US Army Air Corps where he was trained to fly multi-engine aircraft. He served with the Bomber Command at Langley Field until 1933.

Web returned to Woodstock and became a car dealer. He was active in the community becoming President of the Woodstock Rotary Club and a trustee for the Shenandoah Volunteer Fire Company.

In February 1938, Lt. Riley of the Army Air Corps Reserve was called to active duty to serve as the military commander of the Civilian Conservation Corps camp at Elkton, Virginia. In May, he was ordered to CCC Camp NP6 at Fort Hunt, Virginia.

Web was called to active military duty at the start of World War II. He was promoted to major in 1942 and became the Commanding Officer of the 559th Twin Engine Flying Training Squadron where he trained bomber pilots. He retired as a Lt. Colonel in the United States Air Force Reserve after over 20 years of service.

Web had a Chevrolet dealership in Woodstock after the war. He became the President of Chamber of Commerce. He helped establish the Shenandoah County Memorial Hospital and served on the board of directors. He was a board member of the Shenandoah Telephone Company (Shentel) and the Farmers Bank of Edinburg.

He was elected mayor of Woodstock in 1951 and served as a member of the Virginia House of Delegates from 1958 until 1959.

Among his lasting accomplishments in the Woodstock community was the establishment of a public park with a swimming pool, playing fields, tennis courts and picnic areas. The W. O. Riley Park is one of the nicest parks to visit in the Shenandoah Valley.