6. Kutsher’s Hotel and Country Club

Kutsher’s Hotel in Monticello, New York, was opened by Max and Louis Kutsher in 1907 as the Kutsher Brother’s Farmhouse, and later expanded into a hotel in the 1920s. The hotel’s real expansion began in the 1950s when it became one of the premiere destinations of the Borscht Belt complete with 400 resort rooms, a golf course, and views of Kiamesha Lake.

The ballroom of Kutsher’s played host to early performances by many comedic talents such as Jerry Seinfeld and Joan Rivers. In the 1950s and 60s, the hotel also hosted basketball tournaments, and NBA great Wilt Chamberlain once worked as a bellhop there. When the hotel fell on hard times in the early 2000s, Kutsher’s welcomed the All Tomorrow’s Parties music festivals. The hotel was sold and demolished in 2014.