Colleen Shilstone was 16 years old when the photo was taken and was by all accounts a genuine force of nature. A middle child, her elder brother Brian was her senior by a year and her younger brother Bruce was 5 years her junior. Both brothers were at the Prep and Bruce still chuckles when describing her - “self-willed”, “optimistic”, “brave, some might say foolishly so”, “determined to do things her own way” and there was “no task or challenge too difficult for her''.

When war broke out in 1939, like all London’s schoolchildren, the three Shilstones were evacuated from London for safety. Brian, then in the Sixth Form at Dulwich College, was moved to Tonbridge; and Bruce, then at the Prep, left with the rest of Alleyn Park to Cranbrook. At weekends, Brian would happily cycle the 18 miles from Tonbridge to visit Bruce and the two brothers would cheerfully ride around the camp with Bruce on his handle-bars. Colleen was at Streatham High School for Girls at the time and she was taken a little further away to stay with a couple in Brighton who were much stricter than her own parents. There were no such bike rides for her. Neither Mr nor Mrs Shilstone were wholly surprised when she rebelled, ran away, and returned home to Streatham in London after deciding that she would almost certainly “enjoy the bombs more”.

In 1940, the then headmaster of the Prep, John Leakey moved Bruce and the other Prep boys from Cranbrook to Betws-y-Coed in Wales. That move signposted the end of Brian’s weekly bike visits but Colleen, ever competitive with her elder brother, seems to have seen a golden chance not just to one-up him but to do so in style. After all, if Brian could cycle 18 miles to visit their younger brother, why could she not cycle 240 miles from their London home in Streatham to visit her Bruce in Wales? Without waiting for permission, she joined the Youth Hostels Association so that she would have somewhere to stay on the way up and she made sure her sturdy old-fashioned ladies’ bike was fit for the journey. Mrs Shilstone said afterward that when Colleen set her mind to something “nobody was ever really able to stop her. All I could do was to pack her lunch and make sure she had her YHA card.” And with that, off pedaled Colleen. 

In Wales, the Prep had taken on a very different feel. Boys were free to go on adventures on Mount Garmon, to jump into the river and go swimming unsupervised - it wasn’t wild, but it wasn’t far off and it was a world away from wartime London. While there is no doubting her sense of adventure, as Bruce remembers, “at the time, of course, all the focus was entirely on the Germans. There was no real fear of each other - nobody felt anyone you met was a threat as everyone was more worried about those we were at war with.” There were a few wary souls, though. The young English soldier in the photo saw Colleen tagged along to make sure she was safe from what he called “the heathen Welsh people”. 

In the end it took Colleen three days to reach Betws. She booked into a bed and breakfast in Llanrwst, dropped her stuff and cycled straight over to see her brother. Bruce remembers being “both totally surprised and not surprised at all” when she arrived at the Royal Oak, the hotel that the Prep had taken residence in. The weekend that followed sounds like something out of a childhood dream.  “It was the height of summer and I’m not sure the teachers even noticed I was gone,” says Bruce. “We spent the weekend visiting the Cadw castles and enjoying the sunshine. I sat on the back of Coleen’s bike - my legs dangled away as there was nowhere to put my feet - and we had her dutiful soldier riding his motorbike behind us as an escort. The next day we said our goodbyes and Colleen just turned around and cycled home.”

It was a remarkable time and Colleen really was a remarkable young woman. In October, a group of Dulwich Prep London Alumni will be following Colleen’s route home, cycling from Betws-y-Coed to Alleyn Park to raise money for the Great Ormond Street Hospital as well as those who would benefit from a bursary.

Their arrival back at Dulwich Prep London will kick off a whole week of cycling-related activities where families and friends take part in fundraisers, learn how to fix punctures, and experience the Herne Hill Velodrome Bonanza.

Find out more about our Alumni cyclists here and follow the 2021 journey from Betws to Betws with regular updates on our school Instagram account.