Nestled in the foothills of the Catskill Mountains, along the banks of the wild and scenic Delaware River, Callicoon is a community steeped in history and rich in sightseeing opportunities.
Although the hamlet dates back to the 1600’s, very few buildings are older than 1888, a date forever etched in Callicoon history because of a devastating fire that nearly wiped out the entire Main Street.
Begin your walking tour at the Railroad Station. This bungalow- style station was built in 1899, to replace the existing station at the west side of the intersection, which was destroyed by fire. North of the station, along upper Main Street is the Western Hotel with its mansard roof and its Harmonie Hall, a 19th century home to Chautauqua lectures, melodramas, concerts and roller skating. The hotel is also the site of the storied murder of Laura Darling by her bartender husband. Next door to the north stands the less elaborate mansard roofed “Zimmerman Building”. Several doors down is the Callicoon Theater, Sullivan County’s last single screen movie house. Built in 1948, the structure and façade remains much as it was when built more than a half century ago. Crossing the railroad tracks, you will note to your left the “Delaware Hose Co. Firehouse”, now Klimchok Real Estate. It was built for one of the three original volunteer companies that served the town; and the town building later served as Callicoon’s first library, prior to being converted for commercial purposes.
On the south side of Audley Dorrer Drive, stands “Starck’s Saloon”, now the Callicoon Laundromat, known earlier in the century for its “ladies entrance”, serving those patrons too modest to use the front door. Facing Audley Dorrer Drive, Callicoon Coal, twin silos had been used to store coal once delivered to the Upper level directly from the Erie Railroad cars. Turn around and retrace your steps along Main Street. At the north corner of Audley Dorrer Drive, you will find “Matthews on Main” restaurant, the oldest architecturally intact building on Main Street, formerly Percival Plumbing, with its distinctive second story balustrade. Next is the “Layton Building” now Freda Real Estate , one of the few buildings to have survived the fire of 1888. The next building, “Dr. Linda Borrelli, was the site of Lucy Mitchell’s, marking the spot where the fire of 1888 was finally halted. The following building, formerly Metzger’s Shoemakers was destroyed by the fire of 1888 with Mrs. Metzger being rescued from her sick bed and carried across to the Western Hotel. Here she and other Main Street residents were quartered until their homes and businesses could be rebuilt.
The next building was the “Orth Building”, the scene of a 19th century murder, when a bartender used an axe to do in an obstreperous patron. The bartender, incidentally, went unpunished when all the evidence mysteriously blew away during a snowy delivery trip to the Monticello Courthouse.
The building which was most recently The Callicoon Depot restaurant has at various times housed Starck’s Bazaar, a bowling alley and the town’s first movie house, where Edwin Hermann played his own piano compositions during silent movie showings.
“Dyker’s Store”, now Big Willie's Restaurant , served the community’s grocery needs until it became Bennett’s Drug Store. It is believed that the fire of 1888 may have started accidentally in
“The Eickhoff Building” now the Walking Bear Gifts and IOU Thrift Store. “The Delaware House”, now housing Mike Preis Insurance, Baum Law Offices and La Shed Du Fred, complete with ballroom and saloon was considered one of the area’s finest hotels; here Judge Ward held court in the saloon, fining those who disturbed the peace at a rate of “$5 and drinks for the house”.
“The Knapp Brothers Bank”, now home to The 1906 Restaurant, was built in 1906 for a private bank, which failed in 1909, taking with it the savings of many in the community.
The Callicoon Flea Market, formerly “Dr. Kemp’s Pharmacy” and the “A&P Supermarket” survived the fire of 1888, marking the northern end of the fire’s progress. The Callicoon National Bank, now the Delaware Free Library, a neoclassical building constructed in 1913 to house the bank which is the ancestor of The Bank of America now located across the street.
*Buildings listed on the National Register of Historic Places:
The Delaware Free Library built in 1913 is a distinctive, vernacular masonry building with Neo-Classically inspired architectural elements.
Saint James Church and Rectory is an unusual local example of Mission-style church architecture, and an unaltered Queen Anne Style church–related residence.
Callicoon Methodist Church built in 1871 is the oldest church in the Callicoon area. The church itself is typical of vernacular Protestant meeting houses of the post Civil war era in rural New York, and is distinguished by its simple rectangular massing, a projecting bell tower at the west façade, and modest architectural details which conform to the religious fashions of the period.
Delaware Valley Job Corps, formerly Saint Joseph’s Seraphic Seminary is the most visually prominent historic architectural site in the Upper Delaware corridor. The listing includes: the massive U-shaped, slated roofed masonry main building with central bell tower (built ca 1910); the large timber framed barn and three smaller outbuildings (ca 1906); the Romanesque bluestone Holy Cross Chapel (1927); the simplified neo-classical style brick gymnasium (1930); and the surrounding historic landscape and “college pond”.
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