The Pony Club was started in March 1972, by the then school keeper Mr. Crowe.  The first two ponies, Puffin and Tarka were bought from Mrs Hodges by the Parents' Association for £300 from the proceeds of the 1971 Summer Fete. 

At first an unused boys' changing room was converted for use as a stable, then a slightly larger stable emerged from the unused building that was the school kitchen.  As more ponies were acquired, these proved inadequate and so the club expanded into the dining room.  The ponies were kept in an orchard in the summer and stabled in the winter.

In 1975 Mr. Crowe left and a parent, Mrs. Moir, whose daughters Ruth and Judith were already involved with the club, took over.  Since then the ponies have been kept at grass all year round, using the stables only when they are ill, need shoeing, for tuition in stable management and show preparation.</p>

The club currently has the use of eleven ponies, five of which the school owns, and one horse.  There are about 50 members from the ages of 11 to 60+ including several former pupils who join in holiday rides when they are home from university. 

In addition to riding, members learn stable management, general care of the ponies and their tack. Members have taken part in sponsored cross country rides organised by the Rotary Club at Dundridge and charity rides organised by the British Horse Society.

 In May 1983 the Pony Club, which is believed to be unique featured in Horse and Pony, a national magazine. In January 1995 Riding Magazine featured the Rossway UK Chasers course including the school ponies and riders and the June Issue of this magazine included Chesham High School in an article on schools which offer riding.

 Outings are regularly organised for the members, these have included visits to Olympia, the Horse of the Year Show, Royal Windsor Horse Show, The Royal International Horse Show, East of England Show, Badminton, Blenheim, Burghley and Gatcombe Horse Trials, and Equine Event as well as lecture demonstrations.

The club is self supporting and so members and parents organise fund-raising events and help with various jobs, such as mending fences, cutting down docks, moving hay and maintaining the stables. There are regular fund raising events, a jumble sale in the autumn term and social events in January and July. Members also help with local Riding Club events. C.H.S.P.C was awarded the Portwin Cup for the help provided at the Old Berkeley Hunt Riding Club events in 1995 and 2006. 

 An annual highlight for many members was the trip to the Westcott's farm in Somerset. This was started by Mrs Moir in 1975 and sadly, after ceased in 2011.