Before his death from cancer on 14 May, 2014, the 19-year-old from Staffordshire helped raise about £4m for the Teenage Cancer Trust.
He became well known after posting a picture online of himself giving a thumbs-up from his hospital bed.
His mother Jane said it was great to see events still happening in his name.
Organisers said several hundred motorbikes and classic cars took part.
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Participants weaved a 27-mile (43km) rural route through villages between Lichfield and Burntwood.
Mrs Sutton, who rode on the lead bike, said £5.6m had been raised so far for the trust in Stephen's memory.
"The amount is going up all the time and I know that is helping other teenagers with cancer," she said.
Stephen, who died from bowel cancer, took part in the first Ride Out event in 2013.
The trust said £2.7m of the funds raised had been spent refurbishing cancer units at hospitals across the country.
A motorbike ride on the third anniversary of the death of Stephen Sutton has raised £5,500 for the charity he supported.