MILLBROOK, STANFORD, AMENIA, SMITHFIELD VALLEY (EASTERN)
The rolling Millbrook countryside, dotted with horse farms, certainly attracts those seeking an equestrian lifestyle, yet this pastoral landscape grants variety. Excellent public and private schools and shopping and dining in the village make Millbrook convenient for families. The outdoor life is rich in this environmentally conscious region: the sporting lifestyle thrives at area tennis, golf, hunting and fishing clubs, and at the shooting clay course at Orvis Sandanona. Buttercup Sanctuary in Stanford provides a peaceful hiking and birding destination, and historic Bangall hamlet boasts sustainable Red Devon Restaurant & Market. Amenia, situated in the picturesque Harlem Valley, is close to the Wassaic train station and Rail Trail, and appeals to those who enjoy a more rustic, small town life. And bucolic Smithfield Valley, with corn field- and horse farm-lined scenic roads, is home to the Smithfield Guernsey cow herd at Coon Brothers Farm.
CLOVE VALLEY, UNION VALE, VERBANK (SOUTHERN)
Southern Dutchess County presents an ideal family community, with its expansive Tymor Park – at 500 acres, it’s the largest municipal park in New York State – offering a year-round menu of outdoor activities from fishing and camping to swimming and ice skating. For those who like to take to the links, there’s the Union Vale Golf Course, one of the area’s finest. The Clove Valley is home to the Clove Valley Rod & Gun Club for hunting aficionados. Housing ranges from the affordable to luxury, in a relatively undeveloped corner of Dutchess County.
CLINTON CORNERS, MILAN, RED HOOK, RHINEBECK (WESTERN)
For many, the Village of Rhinebeck possesses a city vibe in a small town with its proximity to Manhattan via Amtrak in the neighboring hamlet of Rhinecliff. More densely populated than outlying areas, the historic town -- home to the Beekman Arms, America’s oldest operating inn -- has a wide range of restaurants, shops and attractions. The abundant year-round farmers market and alternative Upstate Films theater draw many visitors. The cultural life is rich with nearby Fisher Center for the Performing Arts at Bard College, and the iconic historical mansions of Hyde Park along the Hudson River. On the outskirts of town, you’ll find Red Hook, Milan and Clinton Corners, home to Clinton Vineyards and a host of prominent horse and cattle farms such as Willowbrook and Uphill.
PINE PLAINS, MILLERTON, COLUMBIA COUNTY (NORTHERN)
Rural Pine Plains offers lovers of the outdoors a rich array of activities: birding at Thompson Pond Preserve; fishing and canoeing at Stissing Lake; hiking on Stissing Mountain; polo at the Mashomack Club; and the annual Stissing Sprint triathlon. Dating to 1782 Stissing House restaurant anchors the town along with additional restaurants, cafes, a traditional supermarket and small town pharmacy. Nearby Millerton, “one of America’s coolest little towns”, charms with its indie boutiques, restaurants, world-famous Harney Tea, and Millerton Movie House. It’s a stone’s throw from the more sedate Connecticut, with picturesque towns of Lakeville and Sharon. Just across the border, in relatively undeveloped Columbia County, are rural dairy towns Ancram, also home to the quaint Ancram Opera House, and Gallatin. Its Roeliff Jansen Kill provides terrific kayaking and fishing.