Hillsdale has access to skiing and the Berkshires
With the Berkshire Mountains as a backdrop, the rural town of Hillsdale attracts longtime locals and seasonal residents who want to live among nature. You have easy access to skiing at Catamount Mountain Resort and all the attractions of the Berkshires, with Great Barrington less than 20 minutes away. It’s generally less busy than the nearby towns of Copake or Chatham, and the land is a little flatter than in next-door Austerlitz, so you get sweeping views. There’s a small town center with a few essentials, but in general, buyers choose Hillsdale for a feeling of being tucked away from it all.
Options for a year-round house or vacation home
You can find a wide variety of price ranges here, from rustic ranch-styles in the $300,000s to luxury properties at $3.5 million. The median home price, around $800,000, is slightly above average for Columbia County. There’s a mix of year-round residents and those who drive in on the weekends from larger cities. “Hillsdale's been a very popular town for second homes up here,” says Joseph Briggs with William Pitt Sotheby’s Realty, who has sold in the area. According to him, buyers drawn to the Berkshires region often choose Hillsdale instead because they can get a bit more value for their money across the New York border. However, New York property taxes tend to be more expensive.
What to expect from rural living
While next-door Austerlitz is more mountainous, Hillsdale is a little bit flatter. “You get some great views because the land is a little bit more open,” Briggs says. It’s a rural area, so most homes use wells and private septic systems. Cell coverage can be spotty, but there’s pretty comprehensive fiber internet coverage, making this area ideal for remote workers. Some residents invest in satellite services like Starlink just in case wired internet goes down during winter storms. During snowstorms, town and state roads are treated quickly. "If you are on a private road, there are plenty of private services available," Briggs says.
Skiing at Catamount Mountain Resort and other recreation
The biggest outdoor attraction in the area is Catamount Mountain Resort, a year-round destination with skiing and snowboarding in the winter, as well as zip lines, hiking and ropes courses in the warmer months. The park’s zip line is one of the longest in the country. “It's crazy. You start on the zip line in Massachusetts, and you end up in New York,” Briggs says. He adds that Catamount tends to be more popular with beginners, while hardcore skiers head farther north into Vermont. You can also drive a few miles south for kayaking on Copake Lake, camping in Taconic State Park or hiking along the Harlem Valley Rail Trail. “There are just lots of areas to do outdoor activities throughout the year,” Briggs says.
Some small-town amenities and restaurants in Hillsdale
The hamlet of Hillsdale is quite small, but it does have some essentials. In addition to the Freshtown grocery store and a post office, you can also find:
- Copake Hillsdale Farmers Market: Seasonal market in a covered barn with the freshest produce from surrounding farms
- Roeliff Jansen Community Library: Community gathering point with books, programs and events
- Sweet Pea's Country Diner: Homestyle diner with fresh-made sandwiches, soups and slices of pie
- Roe Jan Brewing Co: Cozy brewpub with craft beers, outdoor beer garden and regular live music
- Hillsdale House: Historic tavern with a cozy atmosphere and brick-oven pizza
Best public and private schools in the area
On the northwest edge of town, Hawthorne Valley Waldorf School is one of the highest-rated private schools in the area. This kindergarten through 12th-grade school offers an experience-based curriculum integrated with a 900-acre biodynamic farm. For public schools, Hillsdale is part of the Taconic Hills Central School District, which has a single main campus. The massive school was built in 1999, which is relatively modern for this area, and includes an outdoor amphitheater, aquatic center and three gyms.
Drivable to Albany, Hudson and New York City
To reach any city amenities, you’ll have to hop in the car. Here’s what to expect in terms of drive times:
- Great Barrington, less than 20 minutes away, has the closest hospital and large grocery stores
- Hudson is about 25 minutes away, with an Amtrak train that runs to New York City
- Albany is about an hour away and is home to the Albany International Airport
- New York City is a two- to three-hour drive, depending on traffic
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Written By
Catherine Lashley
