Organisers of the two events, one in Ranfurly and the other in Maniototo, are working together on what is being billed as Jazz 'n' Jocks - A Quintessential Central Otago Tour.
The tour will begin in Ranfurly on September 16, two days after the Scotland v Georgia rugby game in Dunedin.
Project Maniototo co-ordinator Amie Pont said as its part of the tour, Ranfurly would host a jazz evening, where the ambience of the 1930s and 1940s would be created.
"Entertainment in local establishments, on the veranda of our local, iconic railway station and art deco hotel will roll out throughout the afternoon and into the evening," Mrs Pont said.
Community groups would be encouraged to hold stalls on the green of the railway station.
The following day, a gala would be held at Anderson Park, in Cromwell. Organiser Glen Christiansen said the feature of the day would be a rugby match featuring former Highlanders and Crusaders players, as well as Cromwell and Maniototo players. The match would begin at 3pm.
Central Otago wine would be featured at the event, and other entertainment would be provided.
Mr Christiansen could not confirm any of the former Highlanders or Crusaders players, but said he was liaising with former Highlander Brendan Laney over who was available.
"It will be a big community event," he said, "very family oriented."
A free bus would transport Cromwell residents to the Ranfurly event and Maniototo residents to Cromwell for the afternoon.
Mrs Pont and Mr Christiansen said they had been told they would receive funding from the New Zealand 2011 Festival Lottery Fund Committee, which had 483 funding applications for 570 events. The committee received applications totalling $76.8 million but it only had $9.48 million to distribute.
The two events were granted a combined total of $31,214 - $13,800 for the gala day and $10,000 for the jazz evening.
Along with the free buses, the money would cover air fares, transportation from Dunedin to Central Otago and accommodation for the jazz entertainers and former rugby players.
