One day in 1987, three colleagues who worked together at Johnson & Higgins (Bermuda) Ltd, Paul Rowlerson, Jon Borrill & Clive Cotton, were walking the Railway Trail when they asked themselves the following questions: (a) Why is it that more people are not using the railway trail?; (b) Could a person walk from one end of the Island to the other in one day during daylight hours?; (c) If they did it, could they convince anyone else to join them; and (d) If they were going to put in all the effort to do it, could the event be used to raise funds for charity? That was the birth of the Great-Grandmother of all walking events for charity in Bermuda: The End-To-End Walk for Charity and Fitness.

The first walk took place in 1988. That year, with a little publicity they found themselves joined by 186 other walkers and many support personnel. The original corporate sponsors were Johnson & Higgins (Bermuda) Ltd; The MarketPlace Group of Companies, and John Barritt & Son. Ltd.

A total of $43,200 was raised that year for charity. In recent years a second walk was added on the same day, the Middle-To-End, from Albuoy's Point to Dockyard.

Those who participate in the End-To-End, whether as corporate sponsors, volunteers, walkers and their supporters, or as organisers probably agree with this biblical quote, (taken out of context) in answering the question "Why put so much effort in this fund-raising effort?'' "And now abideth faith, hope, charity, there three; but the greatest of these is charity.''