5. Wing’s Castle

Photo courtesy Dutchess Tourism

Did you know there is a fairy tale castle in Dutchess County? Right next door to the Millbrook Winery, a popular location for weddings and events, is Wing’s Castle, built by artists Peter and Toni Wing. Peter grew up on the dairy farm that became the Millbrook Winery, and him and his wife began building Wing Castle in the 1970s. The process, the couple say, is still unfinished but there is much to see here nonetheless. The castle is constructed of different sized stones and brick – in fact 80% of the castle is made of recycled materials – with turrets to spare. The interior is in a Tudor style with exposed wood beams and arched vault hallways, decorated with medieval furniture and accoutrements. The moat of the castle serves as the swimming pool and even goes beneath the building itself!

The castle operates as a bed and breakfast, and the rooms have enticing names like The Tower, the Dungeon, and The Annex Suite. There’s also a separate Tudor-style cottage available.