In 1829, it was reported in the Kendal press, that a new inn called the Shakespeare was to be built at the head of the yard that lead to the newly built theatre, and bankrolled by Mr Simpson of Watch Field (now known as Wattsfield) Simpson was well healed, having amassed a large personal fortune from the coach building trade, George III reputedly being one of his patrons.
He also bankrolled the theatre, built to designs by local architect John Richardson. The theatre and the inn opened in 1829, with theatre goers no doubt providing a steady stream of customers. However, under intense pressure from the local Quakers, Presbyterians and Temperance group, the theatre was forced to close only five years .later. It was converted to a billiard room and ball room from this point on.
A map of 1872 shows the Shakespeare and its attendant buildings extending all the way back to Garth Heads at the top of Allhallows Lane, no doubt providing stabling and letting rooms for patrons. In 1869, Jabez Harper purchased the inn for £2430 after previously renting it.
1892 borough Police records state that Jabez's wife, Ann, was the licensee. The inn used to have both a side and front entrance, though the front entrance has now been changed to access for a separate property in the basement. It had ten letting rooms and seating for thirty people, and, reputedly, stabling for 85 horses....though the late Brendan Jameson thought this may have been unlikely given the space behind the inn.
Between 1921 and 1936, various alterations were made to the inn. The bar was moved, the rear of the inn was converted to a lounge area and several buildings to the rear were converted to additional staff and customer bedrooms.
From the mid to late 1920s, the inn was owned by the Collin Croft Brewery Company. By 1937 the inn was in the joint ownership of Messrs. W. Younger Ltd. and Collin Croft Brewery Ltd. In 1950, the inn was owned by three companies, Messrs. W. Younger Ltd, Colin Croft Brewery Ltd and Abbey and Hollyrood Breweries based out of Edinburgh.
By 1957\58, plans state that only Colin Croft Brewery were in ownership. In 1961, Scottish and Newcastle took over. Another survivor that seems to be thriving.