The Lofty Adventures of Dolly Shepherd at Pickering

Pickering Castle, a fine subject for waffling about in a blog post. Built originally of wood on a motte, naturally, because William the Conqueror was far too busy harrying the North to bother with stone at first. Only later did the Normans decide to fortify it properly, as one does, adding a curtain wall, towers, ditches, and all the usual medieval trimmings. Not content with being merely a defensive structure, the castle also served as a hunting lodge, a royal retreat, and even a stud farm. A truly versatile piece of real estate. And for those with a taste for drama, Richard II was imprisoned here around 1339, following his unceremonious removal from the throne. Poor fellow did not even get to stay—he was soon shuffled off to Pontefract.

But, of course, all of this pales in comparison to the far more thrilling saga of Pickering’s ‘Dog Show and Gala’. It was in 1911 that the place truly shone, when the event featured Miss Dolly Shepherd, a woman with a peculiar fondness for dangling from a hot air balloon. Armed with four horses, a waggon, and her trusty balloon, she toured the country, building bonfires to inflate the contraption, only to then float off into the sky, clinging to a trapeze as though it were the most natural thing in the world. At Pickering, however, things nearly went awry. Her balloon, released with all due pomp, decided to flirt with a tall tree. Miss Shepherd, dangling beneath, was rather rudely dragged through the branches but, as fate would have it, emerged unscathed. She waved gallantly as she drifted westward, as though colliding with trees was all part of the performance, before finally deploying her parachute and making a graceful descent.¹Yorkshire Post and Leeds Intelligencer – 27 July 1911

Born in 1886, Miss Shepherd, one must admit, was not short on pluck. She quickly established herself as a leading lady of the skies, performing feats of aerial derring-do that would make most sensible people queasy. Her reputation soared—literally, in fact—as she executed numerous balloon flights and became something of a legend in parachuting circles. On one particularly memorable occasion, she saved a fellow parachutist whose own parachute had inconveniently failed to open. Cool-headed as ever, Miss Shepherd navigated her own chute to rescue the hapless woman, guiding them both safely to the ground. Heroic, certainly, though one wonders why anyone thought leaping from balloons was ever a good idea to begin with.

In any case, Miss Shepherd’s intrepid spirit and fondness for risking life and limb helped blaze a trail for future female aviators. Though whether they thanked her for it is anyone’s guess.

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  Yorkshire Post and Leeds Intelligencer – 27 July 1911