Because of its location on Wappinger Creek, it should come as no surprise that settlers first came to Pleasant Valley to harness the power of water. Milling—cotton, grain, and wood—was big business in here during the 18th and 19th centuries. The building that serves as the Mill Site Museum on Main Street is a reminder of the town’s industrial origins.
Today people are drawn to this Dutchess County town of about 10,000 residents—which is just north of Poughkeepsie and west of Millbrook—to enjoy rural living without sacrificing urban convenience. Easily accessible from the Taconic State Parkway (and just 20 minutes from the Poughkeepsie Metro North station), the town, which is comprised of three hamlets—Pleasant Valley, Salt Point, and Washington Hollow—is a peaceful place to live, raise a family, and enjoy a wide range of outdoor activities.
In addition to bucolic charm, Pleasant Valley boasts a walkable Main Street lined with mom-and-pop shops and casual restaurants. The Pleasant Valley Department store is a family-owned business that has occupied the same building since the 1940s. It’s a great place to purchase name-brand outdoor gear before you explore the 590-acre James Baird State Park, just a 10-minute drive away. The Corner Store Valley is chock-full of great spots to eat as well. The Village Pancake Factory is a local favorite that serves all-day breakfast (there’s a two-page pancake menu!) as well as sandwiches and more; Four Brothers Pizza Inn, a Valley chain that residents rave about, specializes in Mediterranean fare from spanakopita and Greek salad to pizza and spaghetti carbonara; Publick House 23 is the place to grab a drink with 18 taps and a full bar in addition to elevated tavern cuisine (the BEC burger is truly unique); The Grille Wagon food truck on Route 44 specializes in classic barbecue with a twist, like the Hillbilly Burrito piled with mac and cheese, beans, and brisket; and Utterly Delicious is a must-stop for homemade ice cream.
Gifts & More carries women’s clothing and farmhouse décor; and the PV Bike Shop has been helping locals hit the road since 1974. Pleasant
Luckily for locals and day trippers alike, Pleasant Valley offers plenty of opportunities to enjoy the outdoors. When the weather cooperates, Wappinger Creek is a prime spot for canoeing and kayaking. Cady Recreation Park, Memorial Park, and Bower Park are all within walking distance of Main Street; the first two have direct creek access, while Bower has a half-mile “Railroad Trail” that mimics the old Poughkeepsie and Eastern line which operated from the 1870s to the 1930s. Also worth a visit, the 917-acre Taconic Hereford Multiple Use Area (about 4 miles from town) which welcomes hikers, cyclists, campers, and soon, snowmobilers.