Hampshire cyclist and RAF veteran Simon O’Brien is preparing to take his fundraising to Italy this October as he tackles SSAFA’s Ride to Monte Cassino.
Simon, or OB as he is known, will join fellow riders from 1-5 October for a three-day cycling challenge from Naples to the historic Monte Cassino Abbey, raising funds for SSAFA, the Armed Forces charity.
OB spent over 40 years in uniform, 4 years in the British Army and 36 years in the RAF as aircrew on Chinook, Puma and other military helicopters, serving as an Air Loadmaster and leaving as a Squadron Leader. In 2021 alone, he’s raised more than £12,500 for SSAFA through a range of cycling challenges and fundraising activities.
OB first started cycling casually with colleagues in 2019, initially struggling to keep up with more experienced riders. Covid proved to be the catalyst for taking cycling more seriously and it soon became a major part of his life.
OB said:
“Early on during my rides it was clear that cycling was more than exercise. It provided me with space to think and decompress, to reflect and recalibrate.”
Since then, OB has tackled sportives, race circuits, rides around RAF airfields and long-distance cycling challenges, including riding from Vancouver to Whistler.
But there is another reason he keeps getting back in the saddle.
OB has received support from SSAFA himself, something he spoke about when his fundraising was first featured by the charity in 2022. At the time, he said he knew “only too well” how much he valued the help he had received.
OB said:
“I don’t think I’ll ever be able to repay the support SSAFA gave me when I needed it. But knowing every mile I ride gives a little bit back, that’s what gets me through it.”
Beginning in Naples, riders will spend three days cycling towards and around Monte Cassino, through landscapes shaped by one of the most significant campaigns of the Second World War. Expert military historians will accompany the challenge, bringing to life the events, people and sacrifices connected to the campaign.
He said:
“I’ve ridden from Vancouver to Whistler before and that was an incredible experience, but I’m expecting this to top it. I’m looking forward to riding in Italy, meeting the other riders and being part of that camaraderie again.”
OB has already raised around £950 through his cycling in 2026, with Ride to Monte Cassino providing another opportunity to add to that total.
To support OB and his Ride to Monte Cassino challenge, visit.
SSAFA volunteers have been helping the Armed Forces community – regulars and reserves, serving or retired, and their families since 1885. To volunteer or fundraise for SSAFA, or to seek support, visit the SSAFA website and click “find your local branch”.
