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Despite its name (perhaps acquired when the 'Big Road' through Pyle was opened in the 15th century), Heol Fach during the medieval period was part of the main highway through the coastal plain of Glamorgan. Analysis of medieval documents shows that this road descended from Stormy Down along what is now 'Heol Y Sheet' on Broadlands Estate, as far as Cornelly Cross and then headed towards the town of Kenfig. It was probably from this earlier period that it acquired the name of 'Cartway' which is often given as an alternative in 17th century documents. At the 'Croes Y Ddadl' road junction, Heol Fach connected with the ancient trackway leading down from Cefn Cribbwr to the coast. The road to Pont Velin Newydd (certainly in being in the 13th century) and presumably a road leading direct to the town of Kenfig.

Water Street which was part of the Roman coastal road, via Julia Maritima was called 'Heol-y-Troedwyr' (Road of the foot soldiers).

The Julia Maritima from Gloucester to Carmarthen passed Stormy Down, Cornelly, Maudlam and Kenfig to the south of the main road as far as Cwrt-y-Defaid.

The base of this cross stands, almost completely buried by sand in the dunes a little north east of the crossroads formed by the junction of Heol Fach with the road from Marlas to Maudlam. Presumably it marks the original site of this crossroads which has been 'pushed' inland away from it by the advancing sand. The name seems to imply that it was originally a place used by local people as a meeting point at which differences and disputes between them could be settled. If Croes Y Ddadl is accepted as Cross of dispute then perhaps the dissensions that arose here were with merchants attempting to bypass the Borough markets by utilizing the Pont Velin Newydd crossing. In 1843 it was the location chosen for a large public meeting held to voice local unrest at the manner in which the local toll-gates were being operated by the Turnpike Trust.