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Designed by Huntsville-based golf course architect, John Robinson, construction at Whistle Bear began in September 1999 and finished late summer 2000 when the final grow in of grass on the fairways was ready for play on the back-nine holes. The front-nine opened in July 2001. The championship-length links style course has been built over 178 acres of the 232-acre property, that Emilio Cabral and two partners, Carlos DaSilva and Arnold Van Winden purchased in May 1999.

The land was originally owned by one of Cambridge's founding fathers, William Dickson, who sold this parcel to Joseph Bowman, who built Blair's first sawmill in 1821. It was Bowman, who built the original log home, between 1829 and 1832, that is used as the main clubhouse today.

The course derives its name from Thomas Vair, a 19th-century blacksmith who set up shop in the area. Legend has it that Vair would whistle while walking along the country road. Over time, the road that runs along the second and third holes became known as Whistle Bear Road. A check through Cambridge archive records revealed 18 previous owners of the site. Emilio Cabral decided to name all 18 holes after the previous landowners.

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