On a sunny day in May, I found myself dressed in Tweed, standing on the side of the road waiting to be collected by a partner in crime (also tweed-clad) on a classic motorbike with a sidecar. Ten minutes later, we roared into what is usually the sleepy courtyard of the Milk Churn Cafe (yes, home of Sussex Charmer cheese) at The Brickworks near Rudgwick, which was now filled with the splendid sight of 240 plus classic motorbikes and their riders, wearing a spectacular mixture of Tweeds and, in more thana few cases, a fez! Welcome to the Ride of the Ruperts!
What a ride!
The Ride of the Ruperts describes itself as one of the most prestigious motorcycle rides in Sussex. It’s not wrong. Its origins lie in the Distinguished Gentleman’s Ride, a niche but global fundraising event which brings together “classically designed motorcycles, and dapper gentlefolk”!
Ride of the Ruperts itself was formed by a small group who loved the idea of the Distinguished Gentleman’s ride but wanted to make it a bit more accessible, and the event has grown from there! They’ve also now expanded to include an “Oh the Rupettes Ride” (a celebration of women on two wheels, men are welcome if they’ve been invited by a woman) and held in Kent, but we’ll forgive them that, and various other events throughout the year, all raising much-needed money for worthy causes.
From this year onwards, they’re raising money for the Whizz-Kidz charity, which supports disabled children by providing vital equipment such as wheelchairs, as well as providing the support and life skills the children need to reach their full potential. Entry to the ride is charged by bike and you’re encouraged to come superbly dressed, whether you’re driving or pillion. The aim? Dress to impress and have fun. And they do!
The route
Starting from just outside Rudgwick, the 70-mile route heads through the lanes towards Hickstead, the first stopping point. From there, it’s on through the likes of Lewes and Ditchling down to the coast at Seaford for stopping point two before full throttle on to the finish with a private party at an end venue in East Sussex not far from Bexhill, where lunch, liquid refreshment, and live music are available to participants.
The midlife crisis
The roar of 240 motorbikes as they wind their way around the sleepy villages of Sussex en masse is not something I’ll forget easily. But neither is a day spent racing around Sussex in a vintage motorbike sidecar.
Taking to the road in an unusual fashion was all part of my midlife crisis and the event took place one week before my 50th birthday. I was lucky enough to hitch a ride in the sidecar of an original 1950s Danish Nimbus owned by Bo Neilson. It got quite a lot of attention as one of the oldest of the bikes on the ride, and I was glad that, after the thunderstorms of the day before, it turned out to be a glorious day (if a bit nippy in Seaford).
Other bikes included more or less everything from Harley Davidsons, Triumphs and Nortons, but I don’t think I can imagine a better way to fly over the South Downs than in my open-top sidecar, with the wind in my hair and the sun on my face!
We pulled out of The Milk Churn courtyard just after 10 am and purred our way into our final destination some four hours later. The atmosphere was amazing with support from locals along the route and a really friendly and eclectic group of fellow motorcyclists, so much so that at one point I found myself clasped in the arms of a stranger (we were trying to keep warm on the seafront – honest).
Many had a story to tell about surviving prostate cancer or mental health issues. All seemed to have a passion for the road. Driving as a pack uphill and down dale was nothing short of inspirational.
The man behind the roar
The driving force behind the Ride of the Ruperts is Stefano Morrelli, and he really is a force of nature. Having lost friends both to prostate cancer and suicide, he took to fundraising. Lockdown didn’t dampen his efforts. While the rest of us curled up in a ball at the beginning of December 2020, he challenged us all to get out and get active by running, walking, or crawling 10km to raise money for Whizz-Kidz. And raise money it did, raising a whopping £4,500!
As you’d expect, Stefano is a big motorbike fan and a regular rider on the Distinguished Gentleman’s Ride. By starting his own local ride, Stefano was able to open the ride up to more riders and in the inaugural ride in 2018, the ride raised £5,588. In 2025, they raised £56,000, so they are definitely doing something right!
You can find out more about the rides, how to enter and what else they are organising at https://rideoftheruperts.co.uk/. More importantly, you can donate to support their cause at https://www.whizz-kidz.org.uk/, although do make sure you reference your donation Ride of the Ruperts!
And finally, would I do it all again if I had the chance? Yes, without a moment’s hesitation! This mid-life crisis business is a great excuse for having a lot of fun and I was smiling from ear to ear for the duration! Anyone need a pillion?
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