The High Street in Headley lies on high ground between the valleys of the River Wey and the Arford stream, and was simply called The Street in past times. The focal point of the parish, here we have the parish church of All Saints, its rectory and tithe barn, the Holly Bush inn, and the commemorative chestnut tree planted at the triangular road junction.

Over the years, there have been several shops and tradesmen operating here, but, as with so many rural communities, these have now dwindled to a mere handful.

In this section, we make a circular tour from the High Street, down Long Cross Hill to Arford, and back again by way of the Village Green, side-stepping to include a couple of properties, Benifold and The Grange, each of which has its own interesting story to tell.