As the SIRs were craving more pain, more segments were added over the years. A story commonly told is that of one prominent SIR (who shall not be named) in charge of both the route and the whistle, adding Old Peak Road to the route for the first time only to get in a taxi in Stanley leaving the group to carry on bewildered. Whether he handed over the whistle and score card, or not, is not known. There was also the day when less than a handful of SIRs finished in a Black Rainstorm. Oh yes...there was also the new rider - big strong and powerful who, having seen the ride posted in the now defunct Yahoo! group declared it to likely be “a walk in the park”. Haha. He did finish, but walking in his cleats up Luke’s...pushing his triathlon bike.
In June 2016, the format was changed and the TOP became a ride of attrition, including almost every single hill on the island, with a very unsocial start time of 4am. It was a farewell ride to the legendary SIR Steve Drake, and totalled 147km and just a smidge under 4000 vertical metres with a ride time of 8 hours.