Around 300 people will be sleeping rough this winter, according to new Riverina figures collected by Homelessness Australia.
The not-for-profit says a lack of social housing is to blame, estimating a shortfall of around 2900 in the Riverina alone.
Wagga healthcare worker Jodie Godfrey has worked with many homeless people in the past, and she said had heard some truly "horrendous" stories.
"I had a mother who had a child with a chronic illness, and she lived in her car here in Wagga for six weeks," Ms Godfrey said.
"As a mum I couldn't fathom doing that with my children. Nowadays we have so many women who are out there who are homeless with children, couch surfing, sleeping in their cars, wherever they can find to stay safe for the night."
Ms Godfrey will be raising money and awareness for homelessness at this year's Vinnies Community Sleepouts, which will be held over the internet this year due to the coronavirus pandemic.
In other news:
Funds raised from the event will go towards supporting the Wagga Micah Hub, which has helped around 1,200 people access food, financial aid and local services in the past year.
Everyday Caresouth worker Mark Atkinson will also be jumping onto the cause, joining in via Zoom in a show of solidarity with Wagga's homeless.
Mr Atkinson took part in last year's sleepout, and he said he learnt a lot during his night of sleeping rough.
"It makes you realise how tough some people are doing it and how fortunate we are to go back to our nice warm houses and beds and doonas every night," Mr Atkinson.
"People think homelessness is just in the cities, but it's here in our backyards, it's right around the corner from our houses."
The event will kick off on the night of October 23, when Wagga residents will settle down in their cars, backyards, and couches and join the state-wide livestream.
Homelessness Australia's Jenny Smith said the homelessness was a major problem for regional Australia, despite a common belief it was a metropolitan issue.
"People often think homelessness is an issue mainly in cities and CBDs, but the maps show that to be a myth," said Ms Smith.
"The lack of housing that people can afford is not only the biggest cause of homelessness, but it also prevents people escaping from homelessness."