One man was flown to Dunedin Hospital and three others taken to Dunstan Hospital after a trailer tipped on private land in the Lindis Pass, near Goodger Rd, on Saturday.
The person flown to Dunedin Hospital had moderate to serious injuries after the 9.30pm accident, St John spokeswoman Alena Lynch said.
The three had moderate injuries and a fifth man was uninjured.
Constable Paddy Henderson, of Cromwell, said the men were sitting in the trailer being towed around on a "bit of a joyride" when one of its wheels struck on a tussock and it flipped sideways.