The 73-year-old started his walking adventure in 1991 "just for exercise".
"I started walking around the block where I lived. It was getting a bit boring after four or five times so then I thought 'I'll walk all the streets of Dunedin.' I bought a Wises map and started crossing them off," he said.
He worked his way from Mosgiel to Port Chalmers and when he finished, he decided to do it all again.
The shortest period of time it has taken him to complete the streets was one year, and he tried to walk 4km every day.
Mr Henry's latest walk started in November 2009, but this time he was doing it for something else: Ronald McDonald House.
Because of the nature of the challenge, he decided to expand his boundary to include Middlemarch, Karitane, Waikouaiti, Waitati, Henley, Warrington and Brighton.
The 1400km, 1,022,000-step, 581-day journey came to an end yesterday, when Mr Henry was greeted at Plato with a red carpet and cheers from his support group, including wife Annemarie Jorissen.
He raised about $4500 for the charity, which he described as "a really good cause" that did "a wonderful job".
His fundraising meant even more to the organisation after one of its houses "got pretty knocked around" in the Christchurch earthquakes.
The charity was special to him, as he suffers from asthma and emphysema and only has 40% lung capacity.
A stint in a hospital on the Gold Coast made him realise what it must be like for families to be separated when a child needs medical treatment.
Mr Henry has experienced a lot during his 10 walks, from friendly stock animals who "love a rub under the chin" to finding plenty of discarded money.
Though some of the streets in Dunedin are steep, including Ruru Tce in St Leonards which "goes on a long way", some of them were "just magic", such as McIntosh Rd in Brighton, which follows Otokia Creek.
Having recently moved to Wingatui, his next goal is to walk all the streets on the Taieri Plain.
"It's flat," he said.
