Exploring the Counties of the Catskills

Joseph Satto


The Catskills, located at the southern end of New York's Hudson Valley, might be the state's worst-kept secret. Mind you, that's not a bad thing, but upon your first visit, you'll realize it's a place you'll continue coming back to and very much want to keep to yourself.

Sure, there might be more posh outposts—the Hamptons along the eastern tip of Long Island come to mind—but few places call out to residents of the northeast more than the counties that make up the Catskills.

Long a retreat for New Yorkers looking to escape the buzz of the big city, the Catskills offer a lifestyle unlike anywhere else in the country.

From wealthy aristocrats to artistic hippies and all the vibrant personalities that fall in-between, in the Catskills, everyone can find a canvas to call their own.

First, a Little History

First inhabited in the 1600s by Dutch settlers, the area became an enclave for the artistically inclined—mainly artists and writers—in the 1800s. After a century of free-spirited ups and downs—the latter of which including a sanitarium that would turn off visitors for a number of years—the area came roaring back in none other than the roaring 1920s.

This period of the Catskills’ history, and its numerous embodiments, is what many recognize as the region's Golden Era. 

Immortalized in such films as 1987's Dirty Dancing, whose fictitious summer resort is based on the once hopping Grossinger's Catskill Resort Hotel and the area's wider Borscht Belt collective. This is where giant resort hotels entertained predominantly Jewish clientele anywhere from two weeks up to two months each summer.

Then came the mid- to late-sixties and a return to the area's artistic roots, albeit in a completely different genre. At the end of the decade, the town of Bethel in Sullivan County hosted the seminal Woodstock Music Festival.

In the 21st century, the Catskills have emerged as one of the northeast's most sought-after destinations. Whether it’s single-day excursions from New York City or far longer engagements from those further afield, the Catskills, like its history, calls to those from all walks of life.

Let's explore three of the counties that make the modern-day Catskill region such an attractive destination. Not merely a getaway haunt to travel to for a few weeks a year, but also to stay, make an investment, or lay down roots that will last a lifetime.

Ulster County

Population: 185,000
Distance from Kingston, NY to: New York City - 99 miles; Boston - 201 miles, Philadelphia -  178 miles

Ulster County is the beating heart of the Catskills. Sure, Sullivan County might grab the headlines—it draws hippies and vacationers alike—but the towns and hamlets that populate Ulster are what genuinely define the Catskills.

Ulster is arguably the one county in the Hudson Valley that can be all things to all people. Whether you're looking for an active lifestyle, a site for a second home, or want to plant roots and raise a family away from towers of concrete and steel, Ulster provides all of those pursuits and more.

For example, if you've ever wanted to live in a more idyllic version of Brooklyn than the one sitting across the East River from Manhattan—Kingston along the Hudson River is a perfect choice.

Centrally located Stone Ridge is a quaint little hamlet that puts you close to larger Ulster County burgs, the aforementioned Kingston, and New Paltz while keeping their busier pace at arm's length. Real estate in Stone Ridge features an equal number of quaint farmhouses and historic abodes, including on the main street, where homes date to the 18th and early 19th centuries.

Kerhonkson is a throwback to farming villages of the past. It provides a luxurious lifestyle that still keeps one connected to nature. 

Similarly, Accord is the perfect rural retreat for those set on a second home in the Catskills and who want a rewarding and straightforward lifestyle to go along with it. 

If you're more interested in getting into the thick of the Catskill Mountains themselves, the northern towns of Phoenicia and Woodstock are ideal landing spots. Each carries its own level of charm—Phoenicia is the definition of a secluded mountain village, and Woodstock is an upscale farming enclave.

Do you want outdoor adventures? Year-round? There are nearly 70 parks, preserves, and recreational areas in the country with thousands of acres of space to pursue your favorite pastime. 

Is biking or hiking your passion? There are over 350 miles of trails in Ulster County alone. Do you prefer hitting the links instead of the trails? There are ten courses to choose from. Enjoy boating, fishing, skiing, and rock climbing? Yes, all of that is available too.

And while there's plenty of art and culture to rival Sullivan, Ulster maintains strong roots to its farming heritage. There is a vast farm-to-table presence in the community, as evidenced by the many farms, orchards, farmer's markets, and a large do-it-yourself culinary scene. 

Northern Dutchess County and Southern Columbia County

Population: Dutchess - 297,488; Columbia - 65,000
Distance from Poughkeepsie, NY (in Dutchess) to: New York City - 82 miles; Boston - 184 miles; Philadelphia - 164 miles

Although not technically considered part of the original Catskill footprint, the northern stretch of Dutchess County and the southern portion of Columbia County serve as the region's de facto eastern edge.

Dutchess (along with Ulster County to the west) is one of New York State's 12 original counties. The southern portion of the county is more akin to an outlying metro—a large satellite city rather than the more rural well-known areas of the Catskills.

However, the further north along the Hudson River you travel, through FDR's family home of Hyde Park, the association with the Catskills becomes clear. Rolling farmland and gorgeous views within the historic Hudson Valley are commonplace.

Perhaps the most significant distinction between the county line area of Columbia and Dutchess and the heart of the Catskills further west is the relative seclusion offered "on the other side of the Hudson."

Although every part of the larger Catskill and Hudson Valley region has its touristy areas, in Columbia and Dutchess, the scene is less hurried and the overall pace of life is slower.

As for housing, there's plenty of luxury to be found along the Hudson River—hamlets like Barrytown and Annandale-on-Hudson in Dutchess are popular choices. However, for the ultimate in luxury living, venture into Columbia County to the area around Hudson or east to Copake Lake.

Each of these luxury enclaves offers historical homes, expansive estate-style lots, or both. Both southern Columbia and northern Dutchess Counties may not be the Catskill territories you're most familiar with, but you will fall in love with them all the same.

Sullivan County

Population: 75,000
Distance from Monticello, NY to: New York City - 95 miles; Boston - 242 miles; Philadelphia -  174 miles

Yes, this is where Woodstock happened back in 1969 in the small village of Bethel. And if you're a music fan, history buff, or just a straight-up hippy, Sullivan County should rank at the top of your must-visit list. 

Sullivan was also home to The Borscht Belt mainstays that were Grossinger's Catskill Resort in Liberty and The Concord in Kiamesha Lake.

But apart from its notable history, the area remains an enclave for artisans and those who want to immerse themselves within a highly creative atmosphere. Music, art, and an abundance of culture are present in every corner of the county.  

Practically every hamlet has at least one art gallery, one museum, and one performance venue within the region just north of Monticello, a particular favorite of the creative community. And we must not forget that whether you choose to live here or—for now—are just a visitor, your time in Sullivan isn't complete without a trek to Bethel and the site of Woodstock. The well-preserved grounds and associated museum help to teach just how deep Sullivan's free spirit runs. 

The housing in many of these same places are works of art in their own right and represent some of the best real estate in the country. From Liberty to Swan Lake to Lake Superior State Park over to Swinging Bridge Reservoir and up to Monticello, the collection of luxury residences is impressive.

Like much of the surrounding Catskill region, Sullivan is a huge draw for those who love venturing outdoors. 

With an ample amount of wilderness, the area is a sportsman paradise with plenty of hunting and fishing spots. Skiing and snowboarding take up much of the winter activity calendar, with seven locations sponsoring everything from downhill and cross-country skiing to snowmobiling and snowshoeing (even ice fishing).

Of course, once the snows melt, Sullivan features some spectacular venues to golf, hike, bike, and otherwise ensure there's never a dull moment in your summer agenda.

Interested in taking a break from big city life and finding your perfect retreat in Upstate New York? Contact the Fresh Air Realty team today and allow us to be your Catskills and Hudson Valley real estate guide. 


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