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Sugar Loaf, New York was founded in the 1740s as a waypoint along King's Highway, providing supplies and horses to travelers. It draws its name from its similarity to a peak in northern England. 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 mansion estate on Pine Hill Road, on Glenmere lake.
Sugar Loaf is a hamlet of roughly 6 miles length and 5 miles width. It extends from Chester's Durland Hill, near the Chester Library, west into the town of Warwick, into the hamlet of Bellvale. There is a post office at the northeast end of the village. The Village of Sugar Loaf lies within the Town of Chester, and hence shares its area code and exchange, 845, 469. The greater Hamlet extends into Warwick, as well 845, 986. The Hamlet of Sugar Loaf predates the later Town Of Chester, and it was originally administered under the Town Of Warwick. Proponents of the annexation of Sugar Loaf back to Warwick cite this precedent administration.