Sisyphus Challenge 2026: Members meet the challenge of the hill
A relaxed and thoroughly enjoyable weekend brought Guild members together for this year’s Sisyphus Challenge (reports James Male), the event over 8th-11th May combining great roads, good company and a wonderfully varied selection of machinery.
Conceived by Guild committee member John Griffiths, the evolution of the Guild’s traditional touring event was based around the popular Hagerty Hillclimb at Shelsley Walsh, the Guild partnering with the multinational insurance group to deliver a fun event. (Ed’s note: the challenge’s rather appropriate name comes from Greek mythology – Sisyphus considered himself smarter than the gods so was condemned to forever push a boulder up a hill, only to see it roll down again…).
The Challenge began at the aptly named Classic Motor Hub, which proved the perfect rendezvous point for lunch and a briefing ahead of the weekend. Our arrival was quickly overshadowed by a helicopter landing just behind us, its passenger there to test drive a stunning Ferrari 250 SWB sitting proudly on the forecourt. Sadly, neither would be joining us for the remainder of the weekend, but the tone was well and truly established.
From there, the group made its way to Brockencote Hall Hotel for dinner and an overnight stay ahead of Saturday’s hillclimb action. My little Abarth 595, usually confined to London’s 20mph zones, relished the opportunity to stretch its legs across the British countryside – is there anything better on a sunny afternoon?
Saturday again brought glorious weather and a visit to the legendary Shelsley Walsh Speed Hill Climb, organised by Hagerty. The event struck a lovely balance: large enough to provide a fascinating array of cars, yet compact enough to retain a friendly and accessible atmosphere.
One of the highlights was the excellent access to the paddock and viewing areas, allowing spectators to follow cars almost the entire way up the famous hill. The entry list provided an entertaining mix too, from historic rally cars and heavily-prepared specials to Mazda MX-5s and bog-standard Mini Coopers enthusiastically attacking the course. Tickets to tackle the hill itself were also accessible, with several members taking up the challenge.
Combined with the superb weather and relaxed nature of the event, it made for an excellent day of fun, unpretentious motorsport at its purest.
The group later returned to Brockencote Hall for another excellent evening, this time enjoying the hotel’s fine-dining restaurant. Unfortunately, I had to head back to London on Sunday morning, missing the group driving day and final dinner, but the weekend certainly left me wanting more ahead of next year’s event.
A running joke throughout the weekend was that the Sisyphus Challenge could do with an injection of youth. As the youngest attendee, I feel duty-bound to issue a rallying cry to some of the Guild’s less-seasoned members. It proved a fantastic way to meet fellow members, expand my network and enjoy some wonderful driving roads and motorsport, and with multiple cost options available – I hope to see even more faces there next year.
We are sure all involved in the event will join us in thanking organiser John Griffiths, seen here doing some organising… Same again next year, John?
All photos by Jeff Bloxham
