259 Woodstock Road Millbrook, NY 12545

Think of it as Bridgehampton’s rugged, low-key cousin, with a winery and horse population to match. Defined by a timeless, understated elegance that’s kept it fashionable throughout history, Millbrook might just be the Hudson Valley’s best-kept secret — a place that’s hardly of the moment yet always on trend. Socialites and privacy seekers alike are drawn to this bucolic corner of Dutchess County, known for its secluded large-acreage estates, vibrant village, and world-class equestrian scene. In town, you’ll find a quality stretch of design shops, clothiers, and farm-to-table eateries, tended by neighborly folks who know their regulars by name. Cruise the winding back roads past ancient barns and rolling meadows and you’ll stumble upon Innisfree Garden — called one of the country’s 10 best — and Orvis Sandanona, the nation’s preeminent sporting grounds. Situated just 86 miles from Midtown Manhattan, with Metro North nearby in Dover Plains, this secluded yet convenient hunt country is an idyllic escape.