Caldow, of Wellington, has been racing horses for nearly 30 years, and he decided a trip to Oamaru was in order thanks to the juicy maiden stake of $9,000 on offer at the Kurow Trotting Club's meeting.
Caldow and trainer Steven McRae aimed the 5yr-old trotting mare at the Kurow meeting after a discussion three weeks ago.
''I said to the boys we should aim her at this race as it's the best maiden stake in the South Island,'' Caldow said.
''During the week, they felt she was ready to go a good one.''
The Love You mare's task was not easy as she was on the unruly mark and had plenty of rivals to chase.
''You've got 15 horses in front of you that you've get to go around but she did it well and they said she was ready and for me to come down and support them.''
Not everything had gone smoothly in the lead-up to the race, as Mother Nature tested U Dream's mettle.
''She just got caught in the storm in Christchurch. She usually lives outside but they took her inside and she just tied up [cramped] because she wasn't outside.''
Caldow hopes the switch has flicked with U Dream, a half-sister to 2008 Interdominion trotting champion Galleons Sunset, but she will have plenty to offer once her racing career is over.
''She's needed time but she really is a nice long-barrelled mare now. She's going to be a great broodmare - [being] by Love You, and the opportunities that's going to give us in the breeding shed is superb.''
Caldow paid credit to U Dream's first trainer, Steven Reid, who put in a lot of groundwork with the mare for 2 years.
''We've had her since she was a weanling, so it's just been a big mission, but she's on her way now.''
Caldow began his horse ownership in syndication with Gary Allen (now Harness Racing New Zealand chairman) and Keith Gibson in 1984. Doc's Own (six wins) was one of the trio's first winners.
Caldow now shares ownership in his horses with his wife, Barb, and his two daughters, Julia and Sandi (the wife of Canterbury trainer Jim Curtin).
Last season was memorable for Caldow, as he won 20 races across the season thanks to the likes of Star Of Isis, Suu Kyi, Selkie and Zhenya.
