Catskills Small Town Travel

Discover picturesque small towns in the Catskills Region.

Heads up travelers: big cities are out, and small towns are in. In the age of micro-adventures, quick weekend getaways, and unforgettable Instagram moments, the hippest of voyagers are finding new inspiration in relatively unknown places. To discover your own unique small town adventure, look no further than the Catskill Mountains. Spanning four of New York's most beautiful counties, the region's wild lands are dotted with small, Americana towns perfect for your next vacation.

Catskills Small Towns

1. Windham

Our first Catskills small town is Windham. Established over 200 years ago in 1798, it's one of the oldest towns in the region! Often called the "gem of the Catskills," Windham's charming downtown will take your breath away – and take over your Insta feed.

Take a walk down the historic main street to shop boutique stores, or choose a more active day on the bike trails or golf course. When hunger strikes, find mouth-watering refreshments at locally-owned Catskills restaurants with world-class ratings. Despite being small, the town is well-versed in hospitality, offering a wide selection of bed and breakfasts, inns, and resorts for you to choose from.

2. Catskill

Along the banks of the Hudson River, Catskill is a Greene County town steeped in history. Home to the founder of the Hudson River School of Art, and widely considered the father of American art, Catskill is a cultural hotspot. From small downtown galleries to the Thomas Cole National Historic Site, you will find stunning works by up-and-coming artists as well as timeless legends.

Experience for yourself the view that has inspired artists for years atop the Hudson River Skywalk. A mile-long pedestrian bridge spanning the Hudson, the Skywalk provides stunning views of the river and surrounding valley.

3. New Paltz

If you're in the mood for somewhere hip, make your way to New Paltz, a small college town that abuts the rugged Shawangunk Ridge. From scenic hikes with spectacular views to renowned rock climbing at the 'Gunks and breathtaking lakes, New Paltz is a gateway to natural wonders.

It's also a place where art and culture flourish alongside bucolic farm fields and bountiful orchards. Spend a day exploring in Mohonk Preserve or Minnewaska State Park, then drop down into town for a locally-sourced meal and a fresh brew from a local brewery or cider house. If nature's not your game, no worries. New Paltz's Main Street has plenty of shops, coffee houses, restaurants, and performance venues to discover, too!

4. Woodstock

While the small town of Woodstock has become synonymous with the world-famous 1969 festival, it wasn't actually the site of the peace, love, and music we have all come to know. It is, however, the perfect place for a relaxing weekend. Home to Byrdcliffe Art Colony, the nation's oldest arts and crafts colony, the town has welcomed artists and musicians with open arms for over a century, and it continues to do so today.

Live music events are a staple in Woodstock, and surrounding the village green at the center of town you will find unique shops selling handmade crafts from local and visiting artisans. Whether you're looking for creative inspiration, or just a one-of-a-kind stay, Woodstock is a small town you don't want to miss.

5. Bethel

Now that you know the truth about Woodstock, it's time to give credit to the real home of the festival: Yasgur's farm in Bethel, NY. Located in Sullivan County, less than 50 miles south of the festival's namesake town, Bethel has been forever shaped by the events that took place in 1969.

Learn all about the Woodstock Music Festival and its lasting legacy at Bethel Woods Center for the Arts. You can walk the hallowed grounds where musical magic happened, visit the museum, and even catch a live performance on one of their outdoor or indoor stages.

The town of Bethel also has attractions to discover, including the Catskill Distilling Company. One of the first farm distilleries in New York, they brew eight different spirits from all natural, locally-grown ingredients. Stop by the Dancing Cat Saloon to sample to spirits and enjoy a bite to eat.

6. Roscoe

What do you get when you add a bit of wilderness, a dose of farmland, and a generous helping of culture? Roscoe! Not known for one thing, but great for many things, Roscoe provides a well-rounded Catskills experience.

Dine at the Rockland House for an unforgettable meal prepared by acclaimed chefs. Enjoy a pint at the Roscoe Beer Company's Store Front, complete with a self-serve tap wall, a full service tasting bar, and a beer garden. Sleep under the stars at one of several family-friendly campgrounds, or cozy up in style at the luxurious Laurel Lodge.

From Alpaca farms to fishing trips, and galleries to coffee shops, there is something for everyone to do and see in Roscoe.

7. Roxbury

"Quaint" is the word that comes to mind when thinking of Roxbury in Delaware County. Located on the western edge of the Catskills, what was once a small farm town is now a vibrant community and must-see destination.

Much of Roxbury's beauty lies in its history, boasting landmarks like Roxbury Barn, a 167-year-old mountain estate, and Woodchuck Lodge, built in the 1860s, owned by naturalist-essayist John Burroughs, and named a National Historic Landmark in 1962. However, modern times have transformed this small town as well, introducing the Roxbury Arts Group, Plattekill Mountain for skiing, and the somewhat wacky but definitely wonderful Roxbury Contemporary Catskill Lodging, a boutique motel experience offering wildly decorated theme rooms.

If nothing else, make the trip to Roxbury just to stay in the Archaeologist's Digs Cottage.

8. Margaretville

For a swankier small town stay in the Catskills, visit Margaretville. There, you will eat, drink, and sleep like a king or queen. Dine at Trattoria Locale, a family-owned Italian restaurant with daily and seasonal specials inspired by the local farmers' market. Or, stop into the Binnekill Tavern, a Margaretville landmark that recently received new life from new owners.

Choose from a wide variety of lodgings, including the lavish Hanah Mountain Resort and Country Club, rustic Whispering Pines Lodge, or picturesque Hubbell Hill Haven. For a truly soul-cleansing retreat, stay at the Blue Deer Center, which offers workshops and holistic retreats based upon ancestral traditions that aim to help you intimately experience the natural world.

Experience Small Town Travel

When it comes to travel, once you go small, you'll never go back. While big cities are fun from time to time, they are also hard work, and who needs that when they're on vacation? Opt for a small Catskills town and discover just as much fun and excitement while still having the time and space to relax.

Located just North of New York City, small towns in the Catskills are easy to reach, even if you don't have a car. And, with so many to explore, you can return to the region again and again, and a new experience is guaranteed every time.

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