The first bicycle racing in Chesham was at the Chesham Foresters and Oddfellows fete on Whit Monday, May 27th 1890. There were two bicycle events, one and two miles open handicap races. The fete was attended by 2,000 spectators.
The Oddfellows fete became a popular annual event for the next thirty years. At the 1892 fete, the Chesham brass band and the Fife and Drum band both paraded through the town to meet at the Cricket Meadow. There were amusements at the event, including acrobats, a contortionist and the Diamond and Brazier equilibrists*. The bicycle races were dominated by Frank Shorland, who won both the one and two miles handicap events off scratch. It is understood the Shorland rode a geared Crypto.
The Cestreham Cycling Club, which was formed in 1895, started holding their annual sports on August 26th 1899 at the Cricket Meadow. Their meetings included a five miles race was for the Championship of the club and to hold the 10 guinea Lowndes cup. In 1901 it was won for the third time by AH Reynolds and became his property.
The Cestreham CC held their 1900 sports at Berkhampstead Road Athletic Ground, Chesham, but it was not a financial success.
By 1904, the Cestreham Cycle and Athletic Club sports meeting was amalgamated with the Chesham Cricket and Football Club sports and the bicycle events were one and two miles handicap races.
The Oddfellows and Forester's fete was last held in 1914, but was revived on Whit Monday 1920 and drew a large crowd of 4,000 spectators. This was however the last Oddfellows sports meeting at Chesham.
The Cestreham C&AC organised a series of evening running and cycle race meetings from May 1920 for the next three seasons. The British Legion sports took place on the Sports Meadow on August 8th 1923 with bicycle races. The British Legion sports continued for a few years until the meeting on August 3rd 1926, which was probably the last bicycle track racing at Chesham.
The Bucks Examiner of February 11th 1927 summed up the risk of running sports meetings which could be be financially ruined because of bad weather or poor attendance. "The decision of the local branch of the British Legion to hold no sports this year is undoubtedly a wise one, but it is nevertheless very much to be regretted that it is today not worth the risk to hold sports meetings locally, and one gathers that this applies more or less generally."
* A tightrope walker