Winery Run Hunter Valley - which was originally set down for this Sunday - has been postponed until October 10 due to ongoing COVID restrictions.
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Event organiser Paul Humphreys of H Events said it was "impossible" to stage the event in these conditions, with more than 70 percent of the participants coming from Greater Sydney.
Now in its 15th year, the event was expected to bring 1000 runners and 2000 spectators to its new home - the famous Wandin Cricket Pavilion at Lovedale - but Mr Humphreys said about 30 percent of participants have already opted for a refund since the postponement was announced on July 2.
Mr Humphreys said after last year's cancellation, organisers were disappointed to have to move the event once again.
"Like all event organisers, we are in an impossible position to have to work months ahead, expend hundreds of hours and thousands of dollars to prepare these events only to closed down by COVID," he said.
"Our nerves are slowly wearing thin."
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Mr Humphreys said the event was "completed, approved and ready to go", but must now reapply to Cessnock City Council for road event approval, and pay fees to change the date of the development application.
"Our new venue at Wandin is outstanding and the Lovedale community have been very generous to allow the event to take place," he said.
"It's just a pity our event is so complicated, and we must do everything again."
The Winery Run offers a half-marathon, 10.5-kilometre and five-kilometre running events and the traditional Kids Marathon two-kilometre event.
Registrations for the new date can be completed at wineryrun.com.