Willenhall teenager Joseph Guy, known as Joe, died aged 16 after a collision with a van off the A449 Stafford Road near Wolverhampton in May 2017.
Since then members of Wolverhampton Wheelers Cycling Club have organised an annual ride in his memory in aid of the Midlands Midlands Air Ambulance Charity.
On Sunday well wishers joined Joe's family in an emotional minute's silence before setting off on either a 30-mile or a 50-mile courses to and from Aldersley Stadium, in Aldersley Road.
President of Wolverhampton Wheelers Cycling Club and family friend Hugh Porter said: "It was a very day. It was good to see so many come out. Around 250 riders turned up for the seventh Ride for Joe event. Before they set off there was a really nice buzz around the stadium village.
"Before we flagged off the riders we held a minute's hand clap. His is dad Steve was there and his brother Craig who led the ride. There was a really good atmosphere. They riders rolled out clusters of about 20.
"Over the years they have raised about £28,000 for the air ambulance service. I'm delighted to be involved with it. The support this event gets just shows what a strong cycling community we have in the region. Many came from other clubs including people from Stourbridge and it's just wonderful."
Mr Porter, a former world cycling champion, recalled when he first Joe at a community cycling event when he was a young boy.
"Joe and his dad overtook me and as they passed, Joe kept saying to me 'you can do it, you were a world champion' and his words of encouragement stayed with me. When he passed away I struck up a friendship with his family," he added.
The 16-year-old, of Portobello, Willenhall, was hoping to become a professional time trial rider and was on a training ride with a friend when he was struck by a lorry, in Four Ashes, Wolverhampton. Despite the best efforts of the ambulance critical care team he died at the scene.
Ride organiser John Ireson said: “When Joe died, it touched a lot of people, particularly within the cycling community as it is such a close-knit community.
“We said after the first event that we wanted to make sure that this was going to leave a legacy and we all knew Joe really well, particularly for me as chairman and coach.”
A virtual ride was held in 2020 due to the coronavirus pandemic before returning to a full in person event two years ago.