The Clyde to Alexandra road race has a long history. It was first held as a 6 mile handicapped race from Alexandra to Clyde, between the Alexandra and the Leith Harrier and Athletic clubs, on 5 September 1953. Nearly 50 runners competed in mild conditions, tempered with a light breeze. Colin Hicks of Alexandra won the race, D. Forbes of Leith second, with Jim Sprague of Leith third, recording the fastest time of 33.37 minutes.

The event was next held in 1969, when the Harrier section of the Alexandra Athletics club was reformed. It was held on 13 September 1969 from Clyde to Alexandra, an open race of 6 miles starting outside the Clyde fire station and finishing opposite where the Central Stories museum complex is today. Open  to Alexandra club members only, the winner was Murray Ball in a time of 34min 10secs. In 1971 the event was opened to other Otago and Southland harrier clubs, with Harold Genge of Dunedin winning in 30min 22 secs. In 1973 the distance was converted to a metric measurement of 9650 metres.

In 1978 Euan Robertson of Dunedin, just back from the Commonwealth games, recorded the fastest time for the race of 28mins 47secs. This was also the first time the event had received commercial sponsorship, the sponsor being Alexandra Services Ltd. It also had the largest number of runners with 209 harriers competing.

In September 1981, with a new road into Clyde, the race was extended to a full 10,000 metre race. Although held in the first week of September, a late snowfall prevented over 100 runners from attending the first full 10km race. Guy Turner from Invercargill won in 30mins 35secs.

The 10km race was opened to women for the first time in 1982, after representations from the Otago University club the previous year. Previously women were “advised” to compete in the shorter distance of 5800 metres. The Alexandra event was the first in Otago to be open to women and resulted in a record field of 457 runners. 

The Alexandra club was also one of the first clubs in the country to introduce the use of digital stop watches for timing of the event in 1980. In 1982 the Alexandra club introduced another innovation, the use of a large digital clock that could be mounted on the roof of the lead vehicle. They built the clock well, as it remains in use today.

In 1994 the event was opened to recreational walkers. After concerns with increasing traffic in Alexandra with Saturday shopping, the decision was made to alter the course so that runners finished on the outskirts of Alexandra.

In 1995, with the permission of ECNZ (now Contact Energy) the race started on the Clyde Dam, came down the hill and through the main street of Clyde. At the hospital turnoff, they turned onto Muttontown road, before joining state highway 8 to finish opposite the ice rink before Boundary Road, Alexandra. The fastest time recorded on this new course is 29:16 in 1995 by Alan Carmen of the Leith club in Dunedin.