In the late 19th century and early decades of the 20th century cycling was one of Pocklington's most popular pastimes, and Pocklington Cycling Club one of the town's leading organizations.
Numerous Pocklingtonians first took to the roads around the town on their penny farthing machine (first invented in 1870), but cycling really took off after the first 'safety cycle' (with two equal sized wheels and remarkably similar to today's machines) was produced in 1885.
The cycling craze saw many townsfolk quickly acquire bicycles of variable condition, and the more serious cyclists formed Pocklington Cycling Club in 1892. The Cycling Club was soon organizing weekly pleasure rides (both on evenings around local villages and at weekends to places as far away as Bridlington) and competitions and time trials. The time trial between Market Weighton railway bridge and the West Green crossing gates at Pocklington was the most prized record, while the more popular competitions included high climbs up Kilnwick and Garrowby Hills, and then free-wheeling competitions back down again. The club also ran notable socials events such as annual balls and summer galas. Cycle races (usually over one and two miles) were also as popular as running races at the turn of the century at local village feasts and major Pocklington shows and sports.
Pocklington also had its own champion cyclist. George Herbert Stancer was born in Pocklington in 1878 and grew up in the town where his father owned and edited the local newspaper 'The Pocklington Weekly News' in Waterloo Buildings. He became a proficient cyclist at an early age and at 14 was contributing cycling articles to his father's newspaper. He became a British record holder tricyclist in the 1890s, and also later broke the London to Brighton tandem record. He went on to be one of the country's top cycling journalists and administrators and was made an OBE for services to the sport.
Cycling also caused significant traffic problems in and around Pocklington and the newspaper often carried latters and reports of irresponsible and dangerous cyclists and the accidents they caused. Nevertheless its popularity never waned and in the early 1900s there were no fewer than six Pocklington businesses selling and/or manufacturing bicycles
. The cycling club held a Comic Cricket match
in September 1905.