Dickie Frost – Winchester’s Own Champion Cyclist

by | Jan 25, 2026

On a damp Sunday in January members of the Hampshire Lightweights Section of the Veteran-Cycle Club met and displayed some of their machines outside the Winchester City Museum in The Square, Winchester.  The meet was to celebrate the 160th anniversary of the birth of one of the city’s great sporting personalities.

Frederick David Frost, known as Dickie, was born in Winchester in January 1866.  He was the only son of David Frost, a watchmaker and silversmith who ran his own jewellery business at 15 The Square, not far from the Museum.  Frost studied crafts and drafting at the  Winchester School of Art, newly founded in 1870 and originally occupying Winchester’s twelfth-century Wolvesey Castle.  When his father died Dickie took over the family business.

1897 – Dickie Frost (far right in the light colour jersey and cap) – this is the first year that the event was at Crystal Palace

Dickie was an all-round athlete and at an early age won medals for running and swimming becoming a prominent member of the Winchester Harriers but he excelled as a cyclist. In 1898, he won two major trophies, the Bath Road 100 and the Cawardine Challenge Cup which was awarded annually to the winner of a 100 mile race held at Crystal Palace cycle track.  The cup had been donated to the Anerley Bicycle Club in 1895 by its then Vice President H Cawardine, who had a large flour mill in London, to be awarded to the winner of a 24 hour race held at Putney.  Valued at 300 guineas when it was made using 650 ounces of gold, the cup was 4ft 10ins tall.  The following year the race became a set distance at 100 miles and was held at Herne Hill. In 1897 The Cawardine Cup 100 mile race moved to its permanent venue at Crystal Palace where the Anerley Bicycle Club had a club room. The tradition at the time was that if a person won a trophy three times it was theirs to keep.  Unfortunately for the Anerley, Dickie did just that, winning the event for the third time in 1900.

On retirement from cycling Dickie had won nearly every major amateur cycling trophy in Britain.  From then until his death he devoted much of his time fostering sport in Winchester and Hampshire with emphasis on encouraging young people.  He lived his whole life at 15 The Square and died there at the age of 73 just at the start of WW2.

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