Drive far enough north on the Taconic State Parkway and eventually the suburban network of Westchester towns dissolves into orchards and timberland as you make your way into Columbia County. The town of Chatham, NY, at Exit 99, is one of the county’s standout communities and a popular weekend destination.
About two hours north of New York City and bordering the Berkshires to the east, Chatham was a notable trade hub in the 19th and early 20th centuries with Chatham Union Station serving as a thriving railroad junction where four major lines intersected (connecting New York City, Boston, Albany, and Vermont).
Today, Chatham’s Main Street offers everything a day-tripper could ask for: coffee houses, farm-to-table restaurants, a brewery, a fromagerie, highly shoppable boutiques, a tattoo parlor, a holistic wellness center, and the renowned Crandell Theatre (named to the National and State Registers of Historic Places in 2017), home to the annual FilmColumbia film festival.
While the neighboring town of Hudson may steal more headlines for its hipster-chic vibe, Chatham lures visitors and residents with its low-key friendliness. The balance between its deep rural roots and cultural appeal is a big part of the draw: On a Saturday morning, it’s entirely normal to start your day picking up sourdough and local produce at a nearby farm stand, spend the afternoon walking the Albany-Hudson Electric Trail, and finish the evening taking in contemporary dance or open-air theater at PS21—a modern performance venue set directly against a 100-acre orchard. (Art Omi, a 120-acre sculpture and architecture park in neighboring Ghent, NY, is just a short drive from Chatham and another cultural must-do.)
Architecturally, the town is quite diverse, with Federal-style homesteads, restored Greek Revivals, mid-century country retreats, and broad acreage estates all on offer. Buyer demand in this corner of Columbia County is strong, as evidenced by a recent sale at 167 New Concord Road—a custom 6,500-square-foot residence set across 73 private acres with a swimming pool, pond, and panoramic views—which represented the highest single-family sale year-to-date in the Town of Chatham for 2026*.
Brought to market by Joseph Briggs of William Pitt Sotheby’s International Realty, the property drew competitive interest, eventually closing for $2.95 million—$45,000 above the asking price.
Chatham and its neighboring Columbia County towns have long attracted artists, writers, and creative leaders fleeing Manhattan. Notable figures connected to the town include actor David Schramm (Wings), Golden Age actress Marguerite Chapman, and founder of the Coleman Company outdoor gear empire William Coffin Coleman.
Coleman’s legacy can be put to good use during a visit to Chatham at the nearby Ooms Conservation Area, a 180-acre preserve offering three miles of mowed trails through grasslands, wetlands, and pastoral views stretching to the Catskill Mountains. Another close-by spot for outdoorsy types is High Falls Conservation Area, home to Columbia County’s highest waterfall, cascading 150 feet down into a dramatic gorge.
Checking off the walkable Main Street, close-knit community, culturally rich, architecturally significant, and outdoorsy-friendly boxes, it’s not surprising that Chatham’s star is on the rise.
*Source: HVCRMLS, Sold Properties, 1/1/26–8/31/26, Single Family Residential, Town of Chatham, NY.
