The fitness trainer is cycling 2222km around the South Island to mark the anniversary and raise funds for CanTeen, the organisation which assists young cancer sufferers and their families.
Mr Chesterfield (29), of Auckland, began his ride in Picton on January 5, and has cycled down the east coast.
He arrived in Dunedin yesterday on his way to Bluff before heading back up to Picton via the West Coast.
His friend Natalie Morgan was 13 when she was diagnosed with cancer and 19 when she died.
Mr Chesterfield said she was "a beautiful girl" who gave so much hope to other people and showed amazing strength and compassion towards everyone she met.
"Now that [thinking of her death is] not as painful as it was in the past, I feel it's time to bring everyone who knew her together and celebrate the time we had together."
Mr Chesterfield has managed to raise about $3000 for CanTeen.
Donations can be made by logging on to www.fundraiseonline.co.nz/SteveChesterfield/
He departs for Balclutha today.
