Locals Guide: Hillsdale & Chatham

Chatham and Hillsdale are two of those places people move to thinking they’re just buying a house—and then suddenly they have a favorite farm stand, a Saturday farmers market routine, and strong opinions about where to get the best pastries.

Tucked into Columbia County near the Berkshires, this corner of the Hudson Valley feels a little quieter and softer-paced than some of the more heavily trafficked upstate towns, but still full of life. Rolling farmland, hiking trails, ski mountains, historic downtowns, excellent food, and a creative community all folded together.

One of the things we love most about this area is how easy it is to fill out an entire day here. Morning hike, coffee stop, bookstore wandering, long lunch, farmers market, maybe a concert in the nearby Berkshires by night.

Shout out to Upstate Curious agent and Columbia County local Jessica Scott for many of these recommendations (and the photo of Ooms in Chatham bove!).

Eat + Drink

Old Chatham Country Store & Cafe
Part café, part market, part wine bar. Beautifully restored and somehow both stylish and completely unfussy. The dinners are especially good.

Dan’s Diner
A tiny 1920s diner in Chatham with classic counter seating and exactly the kind of breakfast you want after a weekend upstate sleep-in.

Bimi's Canteen & Bar
Cozy, casual, reliably good. Great for brunch, cocktails, or post-house-tour grilled cheese.

Fiesta Cafe
A longtime local favorite for breakfast and lunch with excellent Mexican hot chocolate.

Chatham Brewing
Big outdoor setup, burgers, live music, and one of those places you’ll keep running into people you know.

Bartlett House
A bakery and café inside a gorgeous historic building in Ghent with beautiful pastries, coffee, and farm-driven food.

Hawthorne Valley Farm Store
A biodynamic farm store stocked with produce, bread, cheese, and products from dozens of local farms. Very “this is why people move upstate.”

Little Cat Lodge
Rustic alpine energy in the best way. Fireplaces, cocktails, cozy interiors, and elevated comfort food.

Roe Jan Brewing Co.
A Hillsdale brewery and restaurant with live music, pub food, and a very local crowd.

Twisted Sisters Coffee House
One of Hillsdale’s sweetest newer additions, tucked into the old Harness Shop. Great coffee, homemade baked goods, and cozy slightly-witchy vibes.

Klocke Estate
A stunning distillery and restaurant set among rolling orchards and vineyards in Claverack. Beautiful cocktails, thoughtful design, and sweeping Catskill views.

Outdoors + Culture

Harvey Mountain State Forest
Wooded trails, open meadows, and wild blueberry fields in summer.

Schor Conservation Area
An easy, peaceful hike with big Hudson Valley and Catskill views.

Ooms Conservation Area
Trails circling a pond with great birdwatching and wide open fields.

Roeliff Jansen Park
Walking trails, picnic areas, and the beloved Copake Hillsdale Farmers Market on most Saturdays. 

Art Omi
A sculpture and architecture park spread across rolling meadows in Ghent. One of the most uniquely Hudson Valley places we know.

The Crandell Theatre

A historic indie movie theater in Chatham that’s been a cultural anchor of the town for decades.

Catamount Mountain Resort
Skiing and snowboarding in winter, ziplining in summer, and one of the reasons Hillsdale feels like a true four-season town.

And one of the best parts of living here is how close you are to the Berkshires. In under 30 minutes, you can be wandering around Great Barrington, Lenox, or Stockbridge, catching a concert at Tanglewood Music Center, hiking to Bash Bish Falls, or booking a spa day at Miraval Berkshires (our personal fave!).