Founded by Dutch settlers in 1680, Orangetown is the oldest and southernmost municipality in Rockland, which is somewhat ironic since it’s the farthest from the border with Orange County, located on its complete other side. It was here that Major John Andre, co-conspirator of Benedict Arnold in their treasonous misdeeds, was held in custody at today’s ‘76 House, the old stone tavern in the hamlet of Tappan that touts itself as “the oldest restaurant in America.” Many of Orangetown’s 50,000 inhabitants reside in the villages Grandview-on-Hudson, Piermont, South Nyack, and Nyack, along with a series of defined, unincorporated communities that include Sparkill, Palisades, Blauvelt, and Pearl River. The latter offers train service, on the Metro-North/NJ Transit Pascack Valley Line, and the Palisades Parkway bisects town, making getting around a breeze. You’ll also find countless recreational venues, including Tallman Mountain and Blauvelt State Parks, Piermont Marsh, and several golf courses.