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The 17-year-old and a group of friends were trying to get into a dance party in Watagan State Forest, 20 kilometres west of Lake Macquarie, on Saturday night when he fell down the sheer rock face about 10.30pm on Saturday.
Emergency services and local volunteers abseiled down the cliff about 4am and spent the rest of the night with the injured teenager.
He was winched to safety about 10.30am and flown to Newcastle's John Hunter Hospital with broken bones and suspected internal injuries and is in a serious but stable condition.
"I don't know how he has survived, and the doctors and the paramedics are saying the same thing," said a spokesman for the Westpac Rescue Helicopter.
Acting Superintendent Murray Lundberg said the teenager's survival was "mind boggling".
"I haven't got words to describe his fortunate luck," he said.
He said the teenager and his mates were camping in the forest when they came across the dance party and were denied entry.
The youth apparently thought he could get into the function from around the back, through the bush, with no lights and no knowledge of the terrain, "and he's just fallen off the side of a cliff".
A number of trees had to be chopped down before the teen could be winched aboard the helicopter.
It's understood the boy was trying to get into Solstium Shadows - A Winter Solstice Bush Gathering.
The two-day rave was being held at a site off Rope Road, in the heart of the forest.