The Callicoon Downtown Historic District is significant under criteria A and C at a local level for its history and architecture. It epitomizes the ascendancy, decline and revitalization of rural hamlets in the Delaware Valley in New York. The region was only sparsely settled by the end of the 18th century, when small communities began to coalesce around mill sites and Delaware River landings frequented by rafters transporting timber to urban centers downstream. Callicoon enjoyed a favorable location on the Delaware at the mouth of the Callicoon Creek, which supported a number of saw and grist mills. This situation was vastly improved when the New York & Erie Railroad was routed along the Delaware River with a depot opened in Callicoon in 1848. Rows of commercial establishments were built on both sides of the tracks and along two branches of Main Street (north and south) that paralleled the tracks. The hamlet prospered as a local service center, river landing and railroad stop during the period when the population and economy of the Delaware Valley and adjoining Catskills were reaching their peak. The railroad also brought summer tourists from the city by the hundreds. In 1888 most of the buildings on Lower Main Street were destroyed by a fire, and they were immediately rebuilt in a uniform scale and design that created one of the most distinctive commercial streetscapes in the region. The tightly spaced two- and threestory wood-frame edifices were distinguished by similar parapet fronts with bracketed cornices and paneled friezes, and street-level storefronts tucked under two-story porches. Untouched by the fire, many of the buildings on Upper Main Street pre-date the disaster, although they have evolved over time; these include the Western Hotel, which was expanded under a large mansard roof and later embellished with a Colonial Revival -Mount Vernon - porch in the manner of a motor lodge. Two bank buildings erected in the early 20th century, a mid-19th-century school house enlarged in 1908, a movie theater with an Art Deco front built in 1948 and a third bank designed in a Greek Revival-inspired mode in 1966 are distinctive features that represent the continued evolution of Main Street. On the hillside above Upper Main Street are a number of early buildings, including a Methodist Episcopal Church (1871) and parsonage (1889), a parish school and convent associated with Roman Catholic Church (not extant), a compound containing the home, offices and hospital of a local physician, and the homes of two founding families. Like other commercial centers in the Delaware Valley and Catskills, changing economic, social and transportation factors in summer tourism after the Second World War led to a rapid decline of business in Callicoon. Properties were in limited use or abandoned. When the National Park Service designated the Upper Delaware a Scenic and Recreational River in 1978, important actions were taken to revitalize local economies through renewed tourism that have had a positive effect on the Callicoon Downtown Historic District. Two individual properties containing three buildings within the district were listed on the National Register in 1993 as part of a multiple property nomination for the Historic & Architectural Resources of the Upper Delaware Valley, New York & Pennsylvania: The Callicoon Methodist Church & Parsonage and the Callicoon National Bank. This nomination documents the history of Callicoon's entire downtown in the local context.
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