Scarborough to Middlesbrough, 55.3 miles, 2,894ft of climbing, Five hours 34 minutes

I thought I knew when I woke up on Saturday morning in Scarborough what the challenge of the day’s cycling would be. The gradient profile for the second day of the main programme of the 2022 Herne Hill Whoosh bike ride showed that around 30 of us would be navigating along the beautiful North Yorkshire post through a landscape of steep ups and downs. But I reassured myself that the route was mainly on tarmacked roads and that I am confident hill climber on a bicycle.

The day’s first difficulty was rather different, however. As we rolled out of Scarborough on a bike route known as the Cinder Path, the surface quickly deteriorated into a mess of loose soil, stones and tree roots. It is a mixture that as a tall, imperfectly co-ordinated person riding a large, heavy touring bike persistently find especially hard to negotiate. Riders who had been doing the same pace as I until the surface deteriorated started to slip into the distance.

Things nevertheless started to change a little bit. Recognising that I could not change the poor riding surface, I vowed to come to terms with it. I focused hard on the track surface in front of me, trying to work out the best line through the ruts, stones and dust. As I began to trust my judgment and recognise I was unlikely to fall off, I found my self-confidence – and my speed – slowly picking up.

The process brought to mind the work of the Ebony Horse Club, one of the two charities for which the ride is raising money. The club seeks to build the self-confidence and wellbeing of young people in Brixton, south London, close to Whoosh’s home base in Herne Hill, through giving them riding lessons and other equestrian opportunities. If learning to ride rough tracks better could improve the wellbeing of even a privileged middle-aged man like me, I realised, the process of gaining the trust of horses and learning new skills could be truly transformative for young people such as those with whom Ebony works. Whoosh’s supporters have already pledged £1,180 to the club but my experience on Saturday was a powerful reminder of the good that further gifts could do.

Although my speed on the Cinder Track improved, I nevertheless found myself falling behind and on my own for several miles. I enjoyed picturesque views of Whitby – and a reviving fruit slice from the Whistlestop Café – on my own. It was not until I was climbing the first steep hill of the day – out of the seaside village of Sandsend – that I recognised some of my fellow riders in the distance. I climbed fast to catch up.

The remainder of the day was mainly a story of challenges confronted and overcome. The climb out of Sandsend, while difficult, proved much less formidable than the climb up Bolby Bank, possibly the most difficult I have ever completed. The descent into the seaside resort of Saltburn presented a different test, my brakes screaming as I battled with my own nerves on the vertiginous, twisting road. The last few miles into Middlesbrough were a continuous battle against an unforgiving, cold wind.

The day’s satisfactions were partly the astonishing views of spots such as Robin’s Hood Bay and other parts of the captivatingly scenic coastline.

However, the main sensation on arriving was not the euphoria that often accompanies the end of a day of hilly cycling that finishes with an exhilarating downhill.

It was instead the satisfaction of having confronted a challenge and, in the case of Bolby Bank, literally overcome it. It is in many ways a deeper, more adult emotion than the euphoria. It can be hard to grasp. Yet the other Whoosh riders and I are feeling it at the end of Saturday’s ride – and it is, it occurs to me, the kind of feeling that many of the members of Ebony Horse Club will also at times come to feel.

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