The Roman Road. Much has been written and published about this, the best example being "Roman Ways in the Weald" by Ivan D Margary, first published in 1948. Margary continued the seminal work on the route, begun by local schoolmaster Stephen Vine in 1799. Margary has the road running northwards to London from Pyecombe via Stonepound crossroads/Ham area, down through what is now Little Copse, across the fields behind the Friars Oak Inn and on through to Burgess Hill. In respect of Friars Oak Fields, the straight line path across the first two fields running northwards from Shepherds Walk, is the most likely modern-day indicator of this section of the road.

The Friars Oak area has provided an abundance of Roman finds over the years. The recent construction of the golf course opposite the Friars Oak Inn yielded much evidence and was the subject of professional archaeological excavations. The development of the Shepherds Walk estate in the 1960s is said to have turned up evidence of significant Roman buildings but unfortunately this is not well documented, the evidence having been bulldozed before the importance of what was coming out of the ground was acknowledged.

The field at the rear of the Friars Oak Inn has been used for many things in the past. It was not uncommon for landlords to grow grain crops for their horses in fields near to their inns. King George IV frequently changed horses at Friars Oak when travelling between Brighton and London. The area near the inn was noted for bull and bear baiting, witnessed on one occasion by George IV himself. The small field to the south of the Friars Oak Inn is known as Bullpit Field in reference to these events.