McKendry, who describes himself as a ''young 58'', became the second driver in New Zealand history after Tony Herlihy to rein home 3000 winners when he guided Letz Hope to victory at Parawai Raceway near Thames on February 2.
But, despite beginning his career in his home town of Methven, he is yet to set foot - or sulky - on the grass track at Waikouaiti.
''I wouldn't have driven there before,'' he said.
''Forbury Park I have, and Oamaru I have, but not Waikouaiti - that's a grass track, isn't it?''
McKendry was keen to join a star-studded group of drivers for the five-race series on Tuesday, pitted as a battle between youth and experience.
''It'll be good fun - it's something different,'' McKendry said.
''It works out quite good - we won't miss too much up here.''
The 12 drivers are made up of some of the best young drivers and best older drivers in New Zealand, along with New South Wales junior driver Amanda Turnbull and Victorian trainer-driver Lance Justice.
Justice will join McKendry, Tony Herlihy, Ricky May, Jim Curtin and Allan Beck in the older drivers category, while Turnbull is among the sextet of young drivers with Dexter Dunn, Samantha Ottley, Matthew Williamson, Craig Ferguson and Nathan Williamson.
McKendry said he did no't mind being put into the older drivers' category.
''I only just got in,'' he joked.
McKendry has been an occasional visitor to the deep south in the past since his move north in the 1970s, and drove the late, great trotter David Moss to victory at Forbury Park in 1993.
The meeting is being held under a Waikouaiti Trotting Club licence for the Eastern Districts Racing Club, which had held an equalisator meeting in recent years.
The equalisator meeting had been losing money and the Eastern Districts club decided to seek a race day licence.
Harness Racing New Zealand freed up the day after the Invercargill club took up an offer to move to another date.
Eastern Districts president Andrew Faulks said the outcome had been perfect.
''With the Tuesday meeting being guaranteed turnover, it just makes sense.
''Instead of losing money all the time, we were able to have a race day and give away a few prizes as well.''
Faulks credited Waikouaiti trainer Bruce Negus with the ''youth versus experience'' idea.
''We were just thinking of trying to do something different. It was Bruce's idea to try the young and the old.
''It's a good bunch of drivers, really - especially the two Australians. Lance Justice with [his exploits with] Smoken Up is pretty well known here and Amanda Turnbull was in the young drivers' championship the other week.''
The club will be giving away harnesses, hopples and gear bags across the meeting, and Faulks said each winner would receive a dress rug.
The connections of the winner of the c2 and faster handicap pace will receive a free service to Betterthancheddar.
The winning driver of the series will receive $2000, a scroll outlining their achievement and a trophy, courtesy of Brisbane businessman Greg Brodie, of Courage Under Fire fame.
All five invited driver races are penalty-free.
