Mark Anthony Minton was joined by two friends to take on the challenge which took place around Fordhouses, Wolverhampton.
The group – consisting of Mark, Steve Ray and Phil Garret – have managed to raise more than £1,000 so far, with the event live-streamed on Facebook.
Mark and Steve both dressed as nurses for the challenge, which took around an hour and 20 minutes to complete, while Phil was a second cameraman – with the costumed pair using a GoPro.
Mr Minton, aged 47, said: "It really hits home when you hear from locals some of their heart-breaking personal stories of this terrible virus.
"Everywhere we walked people couldn't say enough about the NHS – and how they'd helped and tried with every breath to help save the lives of their loved ones.
"I came up with a charity walk called 999 NHS walk.
"I decided that at these unprecedented times the only thing that we look forward to is taking out the bin and as we all know the bin goes out more than we do.
"We were dressed as nurses which we thought would be appropriate as we were raising money for the NHS – we wanted raise spirits and have a laugh with the generous local people.
"We both wanted to air our legs and feel liberated due to not get out of the house much due to the lockdown I wore a pair of black stockings.
"I can really see the appeal as it was bitter cold on Sunday and walking into a wind with a full wheelie bin."
Money was raised through Facebook – with people leaving their homes to applaud the men who took on the challenge.
To donate, visit https://www.facebook.com/mark.minton.7