Mr Cross died on September 12 last year, eight weeks after being diagnosed with cancer. He was 36.
He owned rural contracting firm Cross Agriculture and had a love of Case tractors and classic cars, especially Chrysler Valiants.
His fiancee Georgia Redshaw was organising the cruise to leave the South Otago Town & Country Club in Balclutha from 9am on Saturday, September 16.
After the cruise, a prizegiving, auction and a live band would feature at the club.
The cruise was a registered charity, The Moss Cross Memorial Inc, to raise funds to help support families in Clutha when times were tough, Miss Redshaw said.
"Our support will be by referral and in the coming months we will be asking for you to let us know of a family or families experiencing health turmoil."
Her motivation for the charity cruise was how the community rallied to help remove financial strain when she was helping her fiance battle cancer.
"At the time Joseph said ‘when I get better, I want to help someone else out that same way’ but because he didn’t get better I wanted to do something and came up with the car cruise."
The cruise would be an annual event, as a way for their daughter Breeana, 2, to remember her father, she said.
Cruise preregistrations cost $40 per vehicle and $50 on the day.
Register by emailing mosscrossmemorial@gmail.com.