The Gold Hill Cheese Run sees entrants run up the cobbled Shaftesbury street with a 55lb (25kg) cheese.
The event, based on activities of cheese traders in years gone by, began in 2012 as part of the town's food festival.
Barnaby Cox, 18, who has won the race twice, has put his success down to "technique and power".
Organiser Charlie Turnbull said the event was a tribute to a millennia of cheese making in the Blackmore Vale, with "slightly mad" participants racing with the locally-made cheeses which are 35cm (14") in diameter.
"Each one takes up to 500 pints of milk - that's a lot of effort from a lot of cows. But they are not very convenient to carry up a hill."
The street was made famous when it was used in a Hovis bread television advertisement filmed by Ridley Scott in 1973.
It depicted a boy struggling to get up the street on his bicycle to deliver bread to the sounds of Antonin Dvorak's New World Symphony.
A cheese-carrying race up a famous Dorset street is due to take place later.