Bob Woodcock, 67, of Buckingham Way, started off riding from Royston to Land’s End and up to John O’Groats in 2011 - and he’s done it every year since.
He raises money for a charity every year, and this year he has chosen Macmillan - and he hopes to raise £1,000 while on the journey.
Bob will be joined by his biking mascot, Boris the monkey, and his 17-year-old grandson Matthew.
He said: “On June 4 I’m going to be riding from Royston down to Land’s End and then to John O’Groats before coming back down.
“It’s around 2,000 miles and this year my grandson is going to be on the back of the motorbike.
“I started doing this in 2011 as it was something that I’d always wanted to do, but I thought that I’d try and raise some money while doing it and it’s just snowballed from there.
“I’ve done it for quite a few charities in the past and this time I’m doing it for Macmillan - I’m hoping to raise around £1,000 like previous times.
“This could be the last time I do the ride but you never know - watch this space.”
There are sponsorship forms in shops across Royston if you wish to donate to Bob’s challenge.