It was originally just a one-off: Owners Dena and John Finneran wanted to do something special for their guests one autumn, and the old mint-on-the-pillow courtesy was quaint and traditional but somewhat, well, measly. So Dena, a culinary artist, began baking and the yearly Caldwell House tradition was started.
“The pie on the pillow is very special to us. Our guests return each fall to enjoy the pies and the foliage,” she said.
Now in its fifth year, it’s easy to see why a welcome from a slice of fresh-baked pie would be alluring. Finneran bakes up varieties like classic apple, cherry, cream, or “chef’s choice,” really whatever else catches her fancy (for weekend wedding parties that book the entire house, this restriction can be waived). All pies are made in-house using fresh fruits and fillings sourced from local purveyors like Blooming Hill Farm, Soons Orchard, Roe’s Orchard, and Jones Farm.
Rooms also feature a king or queen bed, full bath (several have Jacuzzis), fireplace, and independent climate control. For your entertainment, they each come with WiFi, a smart television equipped with DirectTV, Netflix, and Hulu, and an iPad Mini that’s been preloaded with local information on dining and activities. Outside the comfort of your room, the inn sports six living and game rooms, stocked kitchenettes in both the main building and carriage house, and a formal dining room for daily three-course breakfasts.
Located in Salisbury Mills, Caldwell House is close to the U.S. Military Academy at West Point, the Storm King Arts Center, the Woodbury Common Premium Outlets, and several local wineries. “Pie on the Pillow” days begin the Tuesday after Labor Day (September 4 this year) and run through September 30. Reservations start at $195/night — scrumptious pie included.
25 Orrs Mills Road, Salisbury Mills
845.469.2954 for information
1.800.210.5565 for reservations