John Jolley opened The Rutland Gallery on Uppingham's High Street East in December 2022, after selling the software company he had run in Leicester for more than twenty-five years to return to a lifelong interest in art. He trades as Oakham Galleries Ltd, having bought, collected and sold work for over forty years before taking premises in the town himself. The gallery occupies a building with sections dating to 1472, and shows contemporary painting and sculpture by artists who also exhibit in London and abroad, alongside an online platform called BuyART that connects collectors with artists directly. Jolley, who lives nearby in Manton, is often in the gallery to talk through pieces with visitors rather than leaving sales to gallery staff. Uppingham's concentration of galleries drew him to the town over other options in the county.
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