There facility has two eighteen hole courses, the Pulpit and the Paintbrush, which are located six kilometers apart. The aim of the Devil's Pulpit Golf Association, founded on February 14, 1989, was to establish a private club in the Caledon Hills with two golf courses comfortable enough for the average player while posing an unrelenting challenge to the low handicapper. This dream was realized with the opening of the Devil's Pulpit Course on July 1, 1990, and, two years later, the Devil's Paintbrush. Majority shareholders Chris Haney and Scott Abbott, co-inventors of the popular board game Trivial Pursuit, operate the Devil's Pulpit Golf Association as a non-profit organization and they are actively involved in the day-to-day management of the club. The Devil's Pulpit Course, situated on Highway 10, is named for an Indian legend at the nearby Forks of the Credit River, while the Devil's Paintbrush, three miles east, is named for an indigenous wildflower which blooms both spring and fall. The courses are built on the gentle southern slope of the development-protected Niagara Escarpment. The modern Pulpit Course was built on 315 acres. The design is narrow and features tree-lined fairways with hidden bunkers. The target greens also have sand bunkers protecting them. The signature hole is #1, a 478-yard, par 5, named the "Tower Hole" because from this hole you can see the C.H. Tower, which is the tallest free-standing building in North America. From an elevated tee you have two dogleg fairways to choose from and you can possibly get to the green in two. By contrast, the Paintbrush has a Scottish-Irish feeling from the 164 acres of rolling hills, double greens, stone walls and flowing fescue. This course is more of a links-style design with its wide open fairways and greens that are small. The signature hole is #8, a 574-yard, par 5, which offers a view of an old foundation of a farm house that sits in the middle of the fairway. "Golf Digest" named the Pulpit Course the "Best New Course in Canada" in 1992, and the Paintbrush Course received the same award in 1993. The 6,180-yard men's tee on the Devil's Pulpit Course also has a ladies' course rating of 74.8 and a slope of 138. The 6,001-yard men's tee on the Devil's Paintbrush Course also has a ladies' course rating of 73.1 and a slope of 135.

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