The main village of Lealholm is situated at the bottom of Crunkly Ghyll (sometimes spelled "Crunkley" and "Gill"), a deep cutting where the river emerges into the flat bottom of a glacial U-shaped valley. This was crucial to its development as a settlement, becoming an important crossing point over the River Esk where the valley flattens out, becoming shallow at end of a sharp bend in the river before slowing to a deeper meandering course further downstream. The remains of the fording point are still visible next to the arched bridge used today, which dates back to the 17th century. Three roads lead from the centre of the village, one follows the river up the valley towards Danby; the second heads north past the hamlet of Lealholmside and across the moors towards Whitby; and the third leads south, towards Fryup and Rosedale.