The Olde Boar's head could date back to 1587, Inside the building on a fireplace this date is inscribed. It is also believed there are other date’s inscribed in other areas of the Inn. Inside the cellar there is a 1632 date inscribed. Today you can see clearly that the Inn has seen some modifications over the many years it has stood in the same spot since it was erected. During its long history some of these dates may suggest many different phases of building work. The Inn was at first an old row of cottages before it became a coaching inn, situated on the former Chester to York highway.

During the early 19^th century the session’s house was added to the Old Boar's Head, this became the local court for the village. This is where all the convictions were made and in some cases some people were sent to the gallows. Samuel Bamford’s publication the early years 1849-1859 mentions the Olde Boar's Head, he makes reference to the room called ‘The Thrashing Bay’. According to Bamford this room was used to hold hand to hand fighting contests. It is believed that Bamfords Father in his younger days took part in such a fight, apparently it lasted over 2 hours. The fight did come to an end but his adversary a large powerful man lay helpless on the floor, he had to be carried home by his companions.

The only time the Olde Boar's Head came into serious demise was in 1919 when the local council allocated £18.000 for a memorial to soldiers of Middleton who had lost their lives during the Great War. This memorial was also to be used as the new town hall, the building was to be erected on Long Street. This required the demolition of the Olde Boar's Head! Thankfully the plans never left the drawing board and the Inn survived. Today the Inn is popular for its warm atmosphere, great beer (J.W.Lees) and fine food.