The annual mountain-bike race through the scenic trails around Franschhoek and Paarl in the Cape Winelands takes place from Friday to Sunday.
The 36-year-old Woolcock, who has retired from competitive racing, won with HB Kruger two years ago, but this time he will team up with 19-year-old Hennie Roux.
Following his professional career, the experienced Stellenbosch rider is more focused on helping others and he is relishing the chance of taking Roux through the technicalities of one of the classic three-stage races in the country.
“I have been coaching Hennie since 2017 and he has always been bugging me about doing an event with him,” explained Woolcock.
“Fortunately, these dates fit in with my working calendar and we were able to take up this opportunity.”
Although he added that they had not set themselves any specific goals going into the weekend, Woolcock said he was sure the competitive fires would surface on Friday.
“Definitely my mind will be there to compete, but I am not sure if my body will agree with that,” he joked.
“I am not quite sure how it will pan out this weekend, but we are very much looking forward to the experience.”
Woolcock added that he would recommend to all mountain-bikers that they test themselves in the Winelands Encounter.
“The type of routes you are exposed to in the Franschhoek and Boschendal regions are really great trails and also open to the public.
“This means that most of them are not on private land and it provides you with a chance to go back again and again to experience the variety of routes on offer.”
The Winelands Encounter will be raced over 146km, starting at Boschendal and finishing at the Nederburg Wine Estate in Paarl on Sunday.