It's hoped that hundreds will give up their home comforts for just one night to take part in The Big Tees Sleepout outside Middlesbrough College on Saturday March 16.
Organisers aim to raise £100,000 for a range of local homeless charities and food banks, while helping to significantly raise the profile of homelessness across the Teesside region.
Dozens have already signed up to take part in what promises to be Teesside's biggest ever sponsored sleepout.
Middlesbrough and Teesside Philanthropic Foundation, whose patrons include Middlesbrough FC, club sponsors Ramsdens and Steve Gibson's Bulkhaul, are organising the event with local businesswoman Joanna Wake.
Joanna decided to organise the event, having seen first-hand some of the challenges the homeless face when taking part in a sleepout in Redcar last year.
"The event I took part in opened my eyes so much about just how hard being homeless must be, " said Middlesbrough-born Joanna, who now lives in Stockton.
"You know you'll be cold and uncomfortable, of course, but the night was a journey as I realised with every passing hour the many different challenges you face when sleeping rough.
"If you're sleeping out, the luxury of a hot drink lasts literally seconds because you have a few sips and it's cold. Half an hour later, you need the toilet, which means you have to get cold again by getting out of your sleeping bag - if you're lucky enough to have one.
"Equally, how do you relax enough to sleep if everything you own - which isn't much - is with you in your sleeping bag? It must make you so wary.
"Fortunately, we'll have security on hand for the Big Tees Sleepout, along with the company with many fellow fundraisers, so it will be safe but I promise those who take part an experience they will not regret and will never forget.
"But the challenge is really about raising as much money as possible, " added Joanna, who owns Tees Valley Wedding and Raw Marketing Company, as well as running the Mary Portas pilot on Stockton High Street.
"I think those taking part will find that friends and family readily sponsor them because people like you to suffer in return for their support! Hopefully, it's the nearest any of us will ever come to being homeless."
If you are part of a homeless charity or run a project that you feel could be helped by the funds raised please get in touch.
Teesside entrepreneur and Boro Season Card holder Andy Preston, chairman of the Philanthropic Foundation, which helps community causes across Teesside, added: "I feel strongly that we all share a responsibility to do a little bit often to help those less fortunate and help to improve the social fabric of our community.
"The increase in poverty that is arising from our struggling economy is sure to result in more homelessness, so there is an increased need for the public and business community to dig deep and show their support for their fellow Teessiders - in this case helping to give them basic sustenance in the form of food and shelter."
To take part, participants are asked to sign up, raise as much money in sponsorship as possible and then turn up at Middlesbrough College on March 16. Those taking part are advised bring a sleeping bag and to wear layers of warm clothes including hats, scarves and gloves.
Hot and cold drinks will be provided, as well as toilet facilities. The sleepout will take place between 8pm and 8am on the night of March 16 and morning March 17.
To sign up for the Big Tees Sleepout, visit www.bigteessidesleepout.co.uk and start fundraising. Participants must be aged 16-plus on the day of the event and must register online in advance.