The Bennett School for Girls was originally built in the early 1890s as a resort, and then transformed into a finishing school for young women shortly after 1900. In the 1950s, the school expanded from a two year college to offer four year degrees, along with many additions to the campus, but eventually failed to keep up the pace. The college closed in 1977, and time has not been kind to the wood porches and floors. The town has expressed interest in reusing at least the main building, called Halcyon Hall, but there is an issue with who actually owns the property; so the old college on the hill may stay for a while longer.

11-08-2005 Update: The town of Millbrook has altered the zoning law to allow residential homes to be built on the property, as reported by the Poughkeepsie Journal.