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Scuttlebrook Wake was named after the Cattle brook which flowed through the Leasebourne end of the High Street until it was covered in 1831. Chipping Campden's Scuttlebrook Wake has been held annually on the day following the Dover's Hill Games for at least two centuries. In the Evesham Journal in 1886 it was reported "last week it entered into the minds of several inhabitants of this town to revive an old Wake which many years ago was annually celebrated in the Leasebourne, but which has not taken place for 17 years. The programme included climbing a greasy pole, a donkey race, a married woman's race, a smoking contest, jumping in sacks, plus men's and boy's race. Some of the items ,which in the present day have the charm of novelty, created much amusement, and among these was a ' gorging contest', 2s.6d. and 1s.to the first and second who shall consume half a quartern loaf of bread and a quart of ale in the quickest and cleanest manner."
The World's Fair newspaper described the scene in 1962; the 'fair was built-up in the main street of the town and it was an interesting sight to see in the evening the coloured lights of the amusements and in the background the old grey stoned church and buildings looking down on the merry-makers.' In 1938, the Wake was extended to create the modern format, which includes the crowning of the Scuttlebrook Queen, a fancy dress parade, Morris, Maypole and Country dancing.
The Scuttlebrook Wake always follows on the day after the Robert Dover's Olimpick Games. There is a procession of the Scuttlebrook May Queen from Littleworth to the square, pulled on her cart by the Chipping Campden Morris Men, accompanied by her four attendants and a page boy. She is followed by decorated floats and a fancy dress parade and all shops and houses along the route are encouraged to enter a window competition. The queen is crowned in the square and then she presents prizes to the followers with the best fancy dress. After this the square is filled with entertainment from Maypole Dancing, Country Dancing and Morris Dancing. For the rest of the day it is the fun of the fair with Leasebourne full of traditional fair rides and stalls.