The first ride took place with 400 riders in 1995
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As many as 10,000 motorcyclists are expected to take part in the annual Mega Ride in Devon on Sunday.
They all gathered in Lee Mill in Plymouth before driving along the A38 into the city and onto the Hoe on the 40-mile route.
The event raises money for charity and Devon and Cornwall Police say it is a good opportunity to raise awareness about motorbike safety.
Insp Robin Derges is leading the ride on the force's Harley Davidson.
He said speed cameras and patrol officers will be in the area but there is normally very little trouble.
The first ride took place with 400 riders in 1995.
The organiser of the event, Helen McCrave, said: "It's for local charities and it's an amazing feeling being on the Mega Ride with all the other bikers.
"And up on the Hoe there will be all manner of stands with something for everyone."