In eastern Columbia County on the border of Massachusetts lies the town of Hillsdale, a rural community at the base of the Taghkanic Mountains. Resident Irwin Feld describes being drawn to the region 24 years ago by its inherent beauty and location: New York City was still accessible, and destinations such as Hudson and Great Barrington were nearby. Now full-time residents, Feld (who owns Irwin Feld Design in the hamlet) and his wife find the community to be “one of the friendliest places you can imagine; people are polite, courteous, and trusting. We have each other’s backs here.”
Hillsdale was initially inhabited by the Mahican tribe of the Lenni-Lenape Native Americans, before being taken over by Dutch patroons with the van Rensselaer patent in the late 1600s. The community was then known for its farmland, and would eventually be an important stop during the Revolutionary War when Gen. Henry Knox was transferring cannons from Ticonderoga to Cambridge.
Family Life
Children living in Hillsdale attend schools in the Taconic Hills district; both the elementary and junior/senior high are located in Craryville in the neighboring town of Copake. In the 2022-2023 academic year, the district had a K-12 enrollment of 1,020 students.
The Roeliff Jansen Community Library also serves as an educational hub, hosting programs designed for a variety of ages. Adults can find Zen while practicing Qigong and Tai Chi; online art workshops are provided for teens; and the littles can enjoy regular interactive lectures about animals.
On the Town
You’ll find an ever-growing business district in Hillsdale’s hamlet at the intersection of Routes 22 and 23 in the southern portion of the town (the area was listed on the National Register of Historic Places in 2010). According to Feld, many artists have found a home in Hillsdale, so it’s no surprise that shops are creative and design-forward—for instance, Berkshire Pottery, C. Herrington Home + Design, Foxy & Winston custom stationery and prints, Passiflora Home, Tiny Hearts flower farm, and Irwin Feld Design. Other spots worth a stop include the Hillsdale General Store, HGS Home Chef for kitchen accessories, and Rodgers Book Barn.
After working up an appetite, grab a bite at Cook and Larder, a café selling prepared foods and baked goods; Four Brothers Pizza Inn; the circa 1797 Hillsdale House, which serves comfort food and brick oven pizzas; the season-driven restaurant at the Little Cat Lodge; Sweet Pea’s for diner classics; and Roe Jan Brewing Company for pub fare and craft beer.
Get Out There
Hillsdale residents don’t need to go far to enjoy outdoor activities in all seasons. The Harlem Valley Rail Trail is accessible downtown—it currently stretches all the way south to Wassaic, with branches running up to Chatham in development. There’s also the Roeliff Jansen Park along the stream of the same name, which hosts several events including the weekly farmers’ market that runs through October. In the warmer months, Catamount Mountain Resort runs a zipline tour and an aerial park course, and come winter, the slopes will be open for skiing and snowboarding.
Neighborhood Stats
Area
47.7 sq. mi.
Population
1,862
Median value of owner-occupied homes
$373,000
To find a real estate agent in Hillsdale or any Hudson Valley town check out near-me.hvmag.com/realtors.
Related: Highland Is a Sweet Spot for Hudson Valley Residents and Visitors
