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A race meeting was held at the racecourse at Chestervale on Wednesday, August 11, 1909. So far no references to other race meetings at Chestervale have been noted.
Robert Sidgwick, the owner of Chestervale, put on the race meeting in 1909. Sidgwick, a right-hand batsman, was from Yorkshire in England and had played cricket for Yorkshire in the 1882 season. He presumably came to Jamaica in the 1880s and possibly acquired Chestervale when it was auctioned in 1885. He played cricket for Jamaica in one match in 1895 against the R S Lucas touring team from England. He involved himself in local activities connected with agriculture and the Church of England.
During the early 1900s he was actively promoting Chestervale as a hotel, and the race meeting in 1909 was probably a part of that promotional activity. The racing experiment was apparently not repeated although the meeting was described as a success.
Sidgwick apparently died in 1934, but little is heard of Chestervale again until it became a Youth Camp in the 1950s.