Hudson Valley Fall Getaways and Vacations 2011: The Roxbury Motel, Roxbury, NY

Best fall vacations in the Hudson Valley: The Roxbury Motel, Roxbury, NY (Delaware County) in the Catskills in Upstate NY


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“And now for something completely different.”

Television junkies will recall this catchphrase from Monty Python’s Flying Circus, the British comedy show that aired in the late 1960s-early 1970s. The sentence provides an apropos description of the Roxbury Motel, a western Catskills hostelry whose lavish guest rooms are inspired by cartoons, movies, and TV shows popular during the same time period. Because without a doubt, the Roxbury is — most decidedly — different.

Located in the northeastern corner of Delaware County, the village of Roxbury is about an hour-and-a-half drive from downtown Poughkeepsie. Travelers follow Route 28 across Ulster County, winding through the towns of Mt. Tremper, Phoenicia, and Shandaken. (During the fall, the drive itself is an event, with thousands of mountainside trees presenting a kaleidoscope of autumn color.) A quiet town, Roxbury was the birthplace of two famous men: 19th-century naturalist and writer John Burroughs, and railroad magnate Jay Gould, both of whom still have a presence there (see sidebar).

Lime-green guest room doors welcome you to the 27-room hotel, and hint at the fact that this is not your run-of-the-mill motor inn. The main site includes a circa-1860s house; a 1960s-era motel addition; and a 2007 expansion built by the current owners, Greg Henderson and Joseph Massa, who bought the place in 2003. A separate addition — “built from the ground up” and completed just last year, says Henderson — is directly across the street.

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