Pilgrims Progress

Pilgrims Progress is a Grade II listed building located on Hailes Street in Winchcombe. It consists of two houses that have been combined into one. The right side features a 19th-century front made of squared limestone rubble, which was previously rendered, and has a steeply pitched Welsh slate roof. The left side dates back to the 16th century and is constructed with a box timber frame on a stone plinth, featuring a stone gable and a Welsh slate roof that is at a much lower level than the right side, along with a brick gable stack.

The right half of the building is two storeys high with two windows, which include 2-light casements above 3-light casements. These windows have one horizontal glazing bar and flat elliptical arches, supported by flat wooden lintels. There is a 20th-century door located at the extreme right. The left half is 1.5 storeys tall with one window, featuring a gabled dormer with a 2-light casement above three 20th-century casements set into framing panels. The back wall shows some timber framing.

Inside, the building retains much of its timber framing, along with a solid newel stair, a chamfered and stopped main beam, and an open fire with a window into the former throughway. Upstairs, there is a 4-centred chamfered and stopped opening. This building was formerly known as Nos 27 and 29 Hailes Street.