The first bicycle race at Carisbrooke Castle was the Volunteers fete on 5th August 1872, the bicycle race was open to all comers. No distance was stated and there were three starters. The winner, A Miller, received an electro-plated tankard.
The Coronation holiday race meetings were held from the late 1870's. The Newport Young Men's Literacy Society organised the 1885 Coronation day sports, which was an annual event. The Temperance and Band of Hope Union ran the Coronation sports on July 2nd 1890 which included six bicycle races for ordinary and safety machines. The advertised boneshaker race was cancelled due to insufficient entries.
The Whit Monday meetings commenced in 1884 and ran until 1910. The Volunteer Battalion of the Hampshire Regiment organised the Whit Monday fete in 1887, which attracted 5,000 spectators to watch the sports. There were bicycle races for IOW residents; a 2 miles safety bicycle handicap, a 1½ miles tricycle race and an open 3 miles handicap race in which local men took the top three places
The Foresters and Oddfellows held their annual Fete on Whit Monday 6th June 1892 and the prizes were displayed in FB Meager's, 110 High Street, Newport. The Whit Monday sports often attracted around 4,000 spectators.
The United Temperance August Bank Holiday Fete of 1884 started with a procession from Quay Street to the Castle headed by the Newport town band. The fete had a bowling alley, swing boats, a flower and vegetable show and a choir contest. There were five bicycle races, open 3 miles and 4 miles handicap races and 2 miles handicap for riders under 17 years old. There was a 3 miles handicap race for Isle of Wight residents and an open 2 miles tricycle handicap, the winner HA Waddham was riding a Royal Salvo. The machines (ordinaries) mentioned in the report were; 54" Special Paragon, 53" Newbridge, 54" Invincible, 52" Arab, 52" DHF Premier, 47" Useful.
The August Bank Holiday 1899 meeting was in aid of Newport Football Club. The races included a "run a lap, bicycle a lap and wheel bicycle backwards a lap" event.
The last bicycle race at Carisbrooke Castle was probably the Ancient Order of Foresters meeting on August Bank Holiday 1910. There were running and bicycle races, side shows and the band of the Ventnor Territorials.
