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 chaos of the big city, the Catskills offer a simple 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.

Ulster County

Ulster County is the beating heart of the Catskills. The towns and hamlets within this county are what genuinely define the Catskills / Hudson Valley and, is arguably the one county 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 in the country, Ulster has options for you.

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. 

For those looking for a more urban lifestyle but tucked in a natural setting, Kingston, located 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 a hippie-meets-upscale cultural enclave with a farming history.

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.

Sullivan County
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.

Northern Dutchess County and Southern Columbia County

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.

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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