Castillo de Íscar dominates a hilltop in southeastern Valladolid between Olmedo and Cuéllar, with fortress mentions dating back to 939 when Arab chronicles recorded military campaigns in the region. Alfonso VI initiated repopulation in 1086, establishing a fortified settlement. The castle's oldest structures date to the 13th century, featuring defensive walls and a tower of homage. Between 1478-1493, extensive fortifications added a substantial defensive spur with flanking towers and a protective moat around the plateau. After years of abandonment, the municipality acquired and restored the castle beginning in 1991, transforming it into a vibrant cultural venue. Today it hosts regular cultural and gastronomic programming, with an artisanal microbrewery operating in its courtyard.