Winter's grip tightens on the Kashmir Valley during the forty-day Chillai Kalan, celebrated for its mesmerizing landscapes. Despite enchanting traders, scholars, and rulers for centuries, the harsh conditions of Chillai Kalan pose challenges, especially for the impoverished. Families prepare for winter with woollen clothing, traditional heating methods like Kangri, and sun-dried vegetables. Affluent individuals escape to warmer regions, while the less privileged endure hardships. Power outages and blocked highways compound issues, affecting students and exacerbating economic exploitation. Remote areas face dire consequences, with blocked roads leading to transportation challenges, impacting healthcare access. The narrative highlights the contrasting experiences of winter, echoing the resilience and struggles of the diverse population in the Kashmir Valley.