Let me first admit, I'm unequivocally biased, and was a teenage homer for Sleepy Hollow. Across four years, I fought hard for the #1 slot on my High School team and Sleepy was our home course. Back then, of course, it looked nothing like it does today.
As others have already noted, today's Sleepy Hollow is unquestionably and grossly underrated on a comparative basis to many, many other US classic courses. It has earned, and deserves, a much better ranking on EVERY list from all the magazines through to the beloved CG.
Not that rankings really matter, but it's that good that is deserves to replace many lesser courses ahead of it. I'd go as far as to dare say that it challenges, for the throne of Westchester's Best, the usual stalwart favorites to both it's South and North. That's a tough golf-rich neighborhood to stand out in.
Extensive tree removal, green restoration and expansion, newer maintenance practices and mowing lines, a clear unification to the principles of CBM design, Gil's expert skill and vision, and constant TLC has produced a world-class restoration.
The course avoids over-templating with just enough moderation and mix of variety. It's scale and rolling-topography works to a near-perfect blend of fun, as well as test. It doesn't confront the player with repetition of difficulty like other highly-regarded nearby courses, yet asks just enough strategic execution before yielding many chances to score. I've had to have every shot in my bag working to produce a good round. It's far from easy, but never far from fun.
Perched on hill overlooking the Hudson River, the wind is never far way and the routing exposes it to all four directions, depending on what portion of the course you're on. When the weather permits, fast and firm are the desired ground and green conditions du jour. The walk takes you to all four corners of the property and, although hilly, never feels onerous.
Forget that the club, it's regal clubhouse, it's short course, and it's congenial atmosphere are first-class and often described with adjectives like spectacular. The 18 hole course is the primary attraction and it just doesn't disappoint...period! My personal opinion is that there are few, if any, better parkland courses in the US.