Cllr Bill Lewis joins fund-raisers from across the borough for Hope4's sponsored sleepout on Friday 31 January.
The sleepout challenges volunteers to experience a night of sleeping rough, with only a tent, cardboard boxes or a sleeping bag to protect participants from the elements.
The event aims to raise awareness of rough sleeping and money for Hope4, a charity which supports the homeless by offering a wide range of services in the town.
The charity's Hope Centre, in Newbold Road, provides clothing, showers, hot food and laundry facilities, while staff support clients by helping to secure accommodation and apply for benefits.
Hope4 also runs a winter shelter from December to the end of March, offering the homeless a hot meal and a bed for the night, seven days a week.
And working with the Trussell Trust, Hope4 runs Rugby Foodbank, which provides families and individuals with three-day emergency food boxes on referral.
Hope4 relies on donations and fund-raising events to run its services, and last year's sponsored sleepout raised nearly £10,000 for the charity's coffers.
Cllr Lewis said: "Sleeping rough for one night in the middle of winter promises to be a real challenge, but rough sleeping's a harsh reality hundreds of people across the country face every day.
"The reasons people end up on the streets can be complex and wide ranging, and Hope4 takes a holistic approach to helping the homeless, offering immediate support such as hot meals and shelter while working with clients to find long-term solutions.
"The charity relies on donations and fund-raising to carry out this vital work, and I hope the people of Rugby can support the sponsored sleepout and make a donation."
Georgina Newton, of Hope4, said: "The generous support of the people of Rugby has made Hope4's work possible and, once again, we're grateful to our brave participants in the sleepout and their families and supporters who, through their donations, enable us to provide support to those who need it.
"We're looking forward to having the Mayor with us and hope his night is not too cold or uncomfortable."
To make a donation to the Hope4 sponsored sleepout and find out more about the charity's work, visit www.hope4.org.uk