Although Masham sits on the banks of the River Ure, it doesn’t really feel like a Wensleydale town, for here the Ure is running from north to south through gently rolling hills on the edge of the Vale of Mowbray – the hills that separate Masham from the vale to the east reach their peak on Whitewell Hill at just over 470ft. More dramatic scenery can be found directly to the west of the town, where the valley of the River Burn runs up into the hills on the eastern side of Coverdale.

Masham is best known for Theakston’s Brewery and their most famous product – Theakston’s Old Peculier. After sixteen years in the hands of Scottish and Newcastle since 2003 the brewery has been owned by four of the Theakston brothers, the fifth generation of the family to be involved in the firm. The town also contains the Black Sheep Brewery, established by Paul Theaskston in 1992, after Scottish and Newcastle had taken over the family firm. Both breweries now have visitor centres.

Masham was an important market town, and the town is still somewhat dominated by the market place, located at its eastern edge. During the middle ages the local area, known as Mashamshire, was owned by the de Mowbray family, who were based a few miles further south at Kirkby Malzeard, but like most areas in the dales Masham was also surrounded by monastic lands, in this case owned by Fountains and Jervaulx abbeys. The first of a series of charters for markets was granted in 1250, many free from tolls. By the 18th century the annual sheep fair was one of the largest in the north of England, benefiting from the proximity of the sheep farming areas of Swaledale, Wensleydale and Nidderdale, all accessible along drove roads. The sheep fair is still held every September.

The church of St Mary’s sits at the south eastern corner of the market place, bordering open countryside to the south. The church has a Norman tower with a 15th century octagon bell chamber on top, and topped by a spire. The living of St Mary’s was given to the Archbishop of York during the twelfth century. Although York is only thirty miles to the south east, the Archbishop soon established the Peculier Court of Masham, which freed it from all claims from his officials, but also meant that he no longer had to deal with the parish, which was instead run by the chairman of the Peculier Court. This court also gave its name, and spelling, to Theakston’s most famous bear.

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