The first bicycle race at Piercefield Park was the Chepstow Athletic Meeting on August 1st 1888. There were two bicycle races, over 1 and 3 miles included with the running and jumping events. Riders travelled from Cheltenham and South Wales to compete. The meeting was a success, but unfortunately resulted in a loss of £20.
The committee was not discouraged by the financial loss and organised a meeting the following year on Whit Monday in a field at Crossway Green. The field was very rough, the circuit had a small hill in it and the was a strong wind blowing. There were the usual 1 and 3 miles open races and a 1 mile local race was added.
The Oddfellows organised an Athletics Meeting on August 29th 1894 at Piercefield Park. There was a half mile open race and a one mile handicap race.
Henry Clay, the owner of Piercefield House, had a small racecourse laid out in the park and when he died in 1921, the house and park were bought by Chepstow Racecourse Company who opened a commercial racecourse there. The house was neglected and was used for US Army training before the Normandy landings in WWII. The House is now a shell, but is listed Grade II* reflecting its importance. The racecourse still operates in the park