whele

I have another suggestion, make it easy for yourself and just provide the location of checkpoints. Allow the riders to pick their own routes. if it is done intelligently, hilly routes could be shorter but obviously more difficult, but riders could perhaps choose a flatter route that maybe much easierbut might add an extra few miles.

for example for 100 miles you could have 3 check points which can be visited in any order and receive a stamp on a card, obviously ensure the shortest possible route is approximately 100 miles. With your historic emphasis your check points could even be in castles or other sites of interest. I remember many years ago doing a windmill ride each of the checkpoints was at an windmill.

I like these sort of events as it requires map reading and planning skills as well as cycling skills. You can choose to give the checkpoint locations on the morning if perhaps the start point is a village hall or to post the location of the checkpoints one week before on a website, people can then use google maps to plan their favored route.

This type of event also encourages those rides more inclined to be self sufficient therefore you will not need to provide marshals or sag wagon. of course the checkpoints could easily offer drinks and snacks to riders.