You have thirteen people. A weekend in mind. And a search bar that keeps showing you three-bedroom apartments in Brooklyn and converted barns two and a half hours into the Catskills. The person organizing a group trip for ten to sixteen people near New York City faces a market that was not designed for them….
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There is a five-mile stretch of Route 9 in Westchester County where four centuries of American history are compressed into a single afternoon drive. Washington Irving wrote the nation’s first internationally famous fiction here. John D. Rockefeller built a hilltop estate with views that reach the Palisades. Jay Gould’s Gothic Revival mansion still commands 67 acres above the river. And every October, 125,000 people descend on the corridor to see 7,000 hand-carved pumpkins illuminate an 18th-century manor.
Search for where to stay in Sleepy Hollow or Tarrytown and you will find Courtyard by Marriott, Comfort Inn, Hampton Inn, and a Wyndham conference hotel. This guide introduces the alternative.
You get the call — or the letter, or the text with the photo of the acceptance packet — and everything that follows happens in a blur of pride and logistics. Your son or daughter is going to West Point. The United States Military Academy. Four years that will reshape their life. And yours. Then…