The first bicycle races at Skegness were the Annual bicycle and athletic sports on August 7th 1880 ‘on the new cinder path'. The bicycle events were; 1 mile handicap (open to gentleman amateurs who have never won a prize), 1 mile open and 2 miles open handicap races. The 1 mile handicap race was won by R Cripps of Sandiacre, who is probably the Robert Cripps that went on to manufacture bicycles in Nottingham with Thomas Humber.
The Boston Guardian of April 23rd 1881 reported ‘On Monday (Bank holiday), a series of bicycle races took place in Skegness Cricket Field on a first class cinder path which surrounds the cricket field'. The events, both handicap races, were over 1 and 10 miles. The latter race was enlivened by the presence of HL Cortis, the English champion, who rode in this race, but not as a competitor.
Further bicycle race meetings took place on Whit Monday, June 6th 1881 and Whit Monday May 29th 1882, the races being a 1 mile handicap, 1 mile novices handicap and 3 miles handicap races.
After a good start, bicycle racing at Skegness faltered and the only other bicycle race was when the Robin Hood Volunteer Battalion held their camp and sports at the cricket club on August 3rd 1883. There were 250 entries for the various events with a prize fund of over £40. There was a one mile bicycle event but the main attraction was a tug of war between the Robin Hoods and a Skegness team, the locals winning with ease.
No other bicycle races were held at the cricket club after 1883. The ground is still used by Skegness Cricket Club and it is also home to a squash club and a women's hockey team.