Sugar Loaf is a mixed-use hamlet in Orange County, New York, United States. It is located in the Town of Chester.
Sugar Loaf, New York, was founded in the late 1740s as a waypoint along Kings Highway, providing supplies and horses to travelers.The hamlet may possibly draw its name from its similarity to a peak in northern England.Note that the name of the mountain in Orange County, New York, (as well as the hamlet itself) is somewhat distinguished by the use of two words instead of one.By the early 19th century, Sugar Loaf was a saloon community. Hambletonian 10, the sire of all American standardbred horses, was born in Sugar Loaf in 1848. America's first murder-for-hire occurred on "Calamity Corners" at the intersection of Pine Hill and Hambletonian Roads.Throughout the remainder of the 19th century, and for most of the 20th century, Sugar Loaf remained a quiet, pastoral hamlet with renown for bawdy Apple-Jack saloons and later, during Prohibition, speakeasies for the enjoyment of countless jazz-age revelers en route to the Glenmere mansionestate on Pine Hill Road, on Glenmere lake.