Despite Bishop Lyttelton's suggestion that the great road from Bromsgrove to Dudley once bypassed Halesowen, we must conclude that the existing road pattern is ancient. Before the Norman Conquest, the lord of the manor of Halesowen owned a saltpan in Droitwich and a house in Worcester. The natural connecting route would be a road along the the ridge on which all the medieval farmsteads of Hunnington are situated. This route is referred to in a deed of 1493 when Agnes, widow of Richard Underhill, gave to her son Thomas "a croft of land situate under Romsley Hill with all its appurtenances between the land of Robert Reynolds on the one part and the road leading from Halesowen to Bromsgrove on the other part".
Improvements in roads in the 18th century made it more practical for villages like Hunnington and Romsley to take a fuller part in the trade of the Black Country. The old road which ran from Bromsgrove, through Halesowen to Dudley was turnpiked in 1727. A committee of trustees made up of local gentry and tradesmen was empowered to charge tolls and apply the proceeds to the improvement of the road surface. The gradients of Gorsty Hill, Furnace Hill and Romsley Hill were reduced by diversions authorised by a further Act of Parliament in 1773. The main road through Romsley and Hunnington continued to be repaired by the turnpike trustees until the last Act of Parliament for the Bromsgrove to Dudley road expired in 1876.