Kinderhook. One of the first towns in Columbia County, you’ll find the name on Dutch maps as early as 1614. In fact, Dutch was spoken here until the mid-nineteenth century. The village is refined, unspoiled, and quite impressive as you drive past historic landmarks like the c. 1820 Vanderpoel House; the Luykas Van Alen House, dating to 1737; or Lindenwald, home of our eighth president, Martin Van Buren. Once a haunt (pun intended) of Washington Irving – a pal of Van Buren’s – today’s Kinderhook is home to an abundance of intact, period properties. There’s a gentrified sense of dignity here that may be just your cup of Earl Grey tea. If so, you can frequent a couple of well-regarded cafes on Main Street, make Saturday’s Farmers Market at the village green your place for flowers, organic produce and meats, and music, and enjoy nearby Kinderhook Lake. Don’t miss the views of Kinderhook Creek’s powerful waterfalls in Valatie, an early village within the town. Got kids and thinking of relocating? The Ichabod Crane School District ranks high on the NYS Dept. of Education report card.
Germantown. If you’re in the market for small-town America, this burgh rates. Main Street’s quiet commercial zone is a low-rise pleasure of antique buildings, where part timers and locals mingle at Otto’s Market. Attesting to the revival here, Otto launched a general store (sort of down-home chic) across the street. A gallery has opened, and we hear that a cool NYC chef is planning a restaurant. Outside the village, there are the views; sunsets over the Catskills are staggering. Homes range from the modest to estates on the river, the mood is relaxed and unpretentious, and you’re minutes to Bard’s Fisher Center, Olana, and Clermont. This was where the aforementioned Palatines settled, and place names (a park, road, even a pizza joint) reflect it.
Chatham. Down to earth, family oriented and comfy, Chatham is a favorite of second-home seekers for good reason. The Ichabod Crane School District is a draw. There’s an array of shops on Main Street, a choice of casual dining options, and the popular local pub, Peint o’ Gwrw (you read correctly; the name is Welsh for “pint of ale”). The independently-owned Crandall Theater is a step back in time, and its Columbia Film Festival sells out every year. The village, an early industrial center, was an important railroad hub where the train still lumbers through. Approach from the south, and you’ll pass grand Victorians in all their painted glory. Once you leave the village, you’re into acres of farmland. Farther afield, Chatham Center, East Chatham, North Chatham, Old Chatham (one of the earliest settlements in the town) are tony hamlets, often with charming center squares. This is horse country, home to the Old Chatham Hunt Club. Alpaca country, too (Spruce Ridge Farm is a great family outing), and the Shaker Museum is a must, recalling Chatham’s past as a Quaker settlement.
Claverack. A strong sense of early Dutch history prevails in what was the Van Rensselaer land patent and one-time county seat. Palatine tenant farmers followed in the 18th century, moving from Livingston Manor in search of a kinder, more rewarding life under the benevolent Dutch. Farmhouses of the era still stand proudly, and Route 23, the main drag, is an intact district of 18th and early 19th century houses. Folks are especially preservation minded around here, and we can think of at least one Greek Revival mansion that’s been home to the same family for 200 years. More history: Aaron Burr and Alexander Hamilton tried cases in the local courthouse in 1788. Romantic views across green meadows, the famous Claverack Creek, plentiful orchards (pick your own if you like), farm stands (Holmquest is one of our favorites) make Claverack the place for buyers who want farm country, the occasional yoga class (try the Won Dharma Center) or golf game at the local country club – plus the “big city” attractions of Hudson, minutes away. The town of Claverack encompasses tiny Churchtown, Hollowville, Mellenville, and Philmont, an affordable village enjoying a bit of a renaissance. Note: the Steiner-oriented Hawthorne Valley School is a lure if you’ve got kids and are “going full time.”
Hillsdale. If proximity to the Berkshires is on your list, explore the possibilities in this close-knit community. Second-home owners tend toward creative types from NYC, who make the commute up the nearby Taconic. Antique-house buffs will delight in the town’s Federal, Greek Revival, Gothic Revival, Italianate and Second Empire Victorian houses, large and small. Within the hamlet, Cold Water Street has nineteen listed historical properties, some dating to 1825, once owned by prominent, early residents. Important 19th century barns and carriage houses grace larger properties, and dairy farms and cornfields still dot the landscape. Yes, it’s hilly (hence the name), and building sites in the steep, dense woodlands outside of the hamlet are devoted to newer homes, often quite substantial and modern in design. Shop at the hamlet’s small commercial area, grab a bite at the trendy Crossroads Food Shop, and if you’re into the “outdoorsy, ” enjoy skiing and snowboarding at Catamount, hiking and swimming at Taconic State Park to the south.