History books of Maidenhead tend to deal with the more conventional things expected of them like buildings, people and events. Reference to sporting activity is therefore limited to a fairly small number of well-documented events and when the sport is one which is not particularly fashionable then such references are even more rare.

Such is the case with cycling. And yet Maidenhead must have been in the forefront of the cycling boom which took place in the late 1800s; a club formed at the time was among the first to be founded in the country and an engraving in the British Museum shows ladies at Maidenhead Bridge toll gate enjoying rides on their "Hobby Horses" which were the precursors of the mechanical marvels ridden today. The engraving is dated 1819. The Maidenhead Advertiser of 24 July 1878 refers to the Maidenhead Bicycle

Club holding it's first run on July 18th from the White Hart Hotel to Marlow, the inaugural meeting having been held on the 24th June at the White Hart where it was suggested that it would "revive the old" though there seems to be no reference to the earlier club.

The Cyclist's Year Book of 1894 lists the first Committee members of this club as being recorded in 1879 but there is no further reference to that club either. The club which really seems to have started the wheels rolling in the town came into being, partly at least, from the initiative of one of the local traders, H. J. Timberlake, who seems to have been able to combine business acumen and enthusiasm for the sporting side of the cycling. His race against a runner at Knowl Hill is one of those well-documented events which at the time would have drawn attention to the machines being produced from his Albert Street works, selling them from his King Street shop and making a personal fortune in the process.

These early machines were "Bone Shakers" with wheels (usually wooden) of equal size and with a wooden frame. They differed from the earlier "Hobby Horse" in that the propulsion was by means of cranks operating on the front wheel. This was in the 1860s and some of the oldest clubs in the country were not formed until 1890-1893.

Timberlake's race with the runner was, no doubt, in part, at least, a publicity stunt since he was after all a business man but it was agreed that on the evening of 28 July 1869 he, on one of his Ordinary (Penny Farthing) cycles would race against Louis Rumball over a mile for a side stake of £10 each side. The race was abortive for Timberlake was knocked from his machine by a spectator and so prevented from finishing the race. The runner completed the distance in 4 minutes 57 seconds.

About 1868 H. J. Timberlake retired from business but his brother Tom, took up where his brother left off and by the early 1870s production of the Old Ordinary had taken over from the Bone Shaker. The Ordinary is considered by many people today to be one of the most graceful machines constructed. About this time too Timberlake produced the "Pilot" cycle from premises in Queen Street but later sold the manufacturing rights to Messrs Hickling & Hutchings, who also had works in the town, in about 1879. Around 1885 premises at 85 and 87 Queen Street were built with workshops at the rear where Timberlake employed a dozen or so men to help him build his latest bicycles which by now had changed shape and size to resemble today's machines.  The "Safety" bicycle had all but ousted the Ordinary from the roads and Timberlake continued production up until the first World War when mass production spelled the end of the road for many of the smaller manufacturers.

Tom Timberlake was an innovator too and many new ideas were taken up at this time. He installed an electro-plating plant soon after the process was invented, making his own electricity for the process. He had shops in Marlow, Hoddesden, Eastbourne and Sevenoaks at the height of the cycling boom as well as the establishment in Maidenhead. In 1887 he was awarded a medal at one of the earliest cycle shows for "Excellence of Manufacture and Design" in 1887.

His prowess as an active cyclist is illustrated by tours on an Ordinary in England, Scotland and Ireland. One day he accepted a dare to cycle across Maidenhead bridge - on the parapet!

His engineering skill and inventive mind produced the first rim brake and later produced machines with novel gearing systems. But it was an Ordinary race which led to the foundation of the most influential of the town's cycling clubs. The story goes that a group of Maidonians had raced one another on their Ordinaries on the Fair Mile at Henley and during the after- race chat the idea of forming a club was born.