Emotional reflection, as well as exertion and joy, on SSAFA’s Ride to Monte Cassino

22 October 2026

Eighteen determined cyclists have completed an unforgettable 195-mile ride through Italy raising some £36,797 for SSAFA, the Armed Forces charity conquering 3,079 metres of elevation and creating memories that will last long after the final pedal stroke.

SSAFA’s Ride to Monte Cassino brought together demanding climbs, sweeping scenery, and the warmth of local communities. Coinciding with the Feast of Saint Francis of Assisi, the riders found themselves caught up in a lively town celebration. With the streets filled with festivities, they climbed off their bikes and embraced the atmosphere before continuing their journey.

Cassino provided, understandably, one of the ride’s defining moments. 

The Battle of Monte Cassino was a series of four brutal Allied assaults from January to May 1944. The goal was to break the German Gustav Line and capture Rome. The campaign resulted in an Allied victory after heavy fighting and the bombing - and destruction - of the historic hilltop Benedictine abbey.

After a gruelling ascent, the group reached the summit to applause, congratulations, and spontaneous donations for SSAFA from passers-by. The descent brought another memorable encounter when a herd of cows moved into the path of the cyclists, briefly bringing the riders to a standstill.

There were moments of intense emotional reflection, as well as joy and physical exertion.

Below the now-rebuilt abbey is a Commonwealth War Graves Commission cemetery where some 4,300 Commonwealth troops are at rest. The cemetery also contains Cassino War Memorial, which commemorates the 4,000 Commonwealth soldiers with no known grave.

The party took time to visit the cemetery, with some placing crosses on the graves of their fallen relatives, or doing so on behalf friends and work colleagues.

Throughout the ride, small acts of hospitality lifted spirits: freshly made focaccia at rest stops, much-needed coffee and pastries, and a café owner who appeared with a tray of sliced panettone to celebrate the group’s journey.

“I thought the support and camaraderie climbing up to the Abbey at Cassino was the high point – no pun intended,” quipped one cyclist.

Another rider chose “everyone bonding together, sharing our stories, and looking out for one another” as their most memorable moment.

Hannah Siddle, SSAFA’s Challenge Events Manager, accompanied the cyclists. She said: “That spirit of shared endeavour carried the riders across every mile. The physical challenge was considerable, but it was the encouragement, friendship, and shared purpose within the group that made the experience so powerful.”

The feelings of all who took part were summed up with: “It was a challenging ride, but an absolutely fantastic experience. I couldn't have asked for a better group of people to share it with, the organisation was superb, and doing it all for such a great cause made every mile worthwhile.”