This club has three nine hole courses that are played in three eighteen hole combinations. The design of the course was altered in 1956 to accommodate construction of the Garden State Parkway. The fairways are narrow, and the greens are in excellent condition. There are water hazards that come into play on eight of the twenty-seven holes, plus many sand bunkers are spread throughout the courses. Many of the fairways are doglegs, veering both to the right and left.

The club hosted the Senior PGA Tour's Cadillac/NFL Classic from 1994-2002. These courses were originally designed by A. W. Tillinghast and redesigned in the 1950s by Robert Trent Jones. The Upper Montclair Country Club is known to have the preeminent caddie program in the state of New Jersey.

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