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Things to Do in the Catskill Region Skip to content

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Small-Town Gems in New York’s Catskills

A summer getaway in Sullivan County offers much more than Woodstock history

Monument of the 1969 Woodstock Music Festival

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Bethel Woods Center for the Arts is the original location of Woodstock.

Woodstock has loomed large in my imagination since I was a kid and my dad introduced me to Creedence Clearwater Revival, the Band, the Who, and Crosby, Stills and Nash — all bands that appeared 50 years ago this summer at the three-day counterculture celebration of peace, love and music that came to define the 1960s.

It would be years before I learned that Woodstock didn’t take place in the town that shared its name, but 60 miles west in Sullivan County — an area once famous for the borscht belt resorts and bungalow colonies that catered to Jewish New Yorkers.

The western Catskill region has awaited a renaissance since the resorts’ decline in the 1980s, with several false starts over the years. But these days the revival truly is underway. Travelers have begun to rediscover Sullivan County’s abundant natural beauty. Trout fishing, which attracted visitors in the 19th century, still thrives, while area farms burst with provisions that stock local markets and farm-to-table restaurants. And with this year’s 50th anniversary of the famed Aquarian Exposition, the region is ripe for exploration.

Planning a visit? Here are a few of my favorite Sullivan County gems to get you on your way.

Downtown Callicoon as seen from Pennsylvania across the Delaware River.

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Downtown Callicoon features many restaurants as well as Nine River Road.

Callicoon

Once a thriving depot on the Erie Railway, the historic town is again gaining steam as one of the western Catskills’ most buzzworthy hubs; it’s a good base for your visit to the county.

Consider lodging at Nine River Road, a cozy farmhouse B&B on the Delaware River. The inn, where guests arrive to a plate of cookies and a handwritten note accompanying their room keys, is a short walk from Callicoon’s charming downtown and an easy jaunt along Route 97, also known as the Upper Delaware Scenic Byway, to other spots around the area. Another option, about five miles from Callicoon in the one-horse hamlet of North Branch: the North Branch Inn, a chic, vintage hotel with 14 rooms spread over three buildings.

New shop owners and restaurateurs have begun hanging their shingles throughout Callicoon. You can catch a flick at Callicoon Theater — a retro, single-screen movie house — or sample craft beers at the Callicoon Brewing Company.

If you’re hungry, a few minutes’ drive south of Callicoon is the Cochecton Fire Station. Owned by longtime friends and craft cocktail aficionados Josiah Early and Ezekial Miller, and housed in — you guessed it — a historic fire station, offers a menu featuring delicious fare such as macaroni and cheese, skirt steak, and cedar plank trout, all prepared in a wood-burning oven.

Fly fisherman stands knee deep in river casting his line

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Fly fishing is a popular activity in Livingston Manor.

Livingston Manor

A big sign proclaiming “Small Town — Big Backyard” welcomes visitors to quaint Livingston Manor, a 10-minute drive from Callicoon. The tagline is accurate: Hundreds of miles of trails wind through lush forests, circle pristine ponds and follow riffling, world-class trout streams just minutes from Main Street. Get the 411 at Morgan Outdoors, where proprietor and Sullivan County trail guru Lisa Lyons takes stock of your footwear and interests before sending you out on an adventure.

She has a special affinity for the region’s historic fire towers. At one time, fire lookouts kept watch over the Catskill Forest from 23 different observation posts. Of the five remaining towers, the one atop Red Hill is the most accessible. Making the trek on a clear day ensures unparalleled Catskill Mountain vistas in all directions.

Given that Livingston Manor fancies itself the “birthplace of American fly-fishing” and nearby Roscoe holds court as “Trout Town, USA,” the Catskill Fly Fishing Center and Museum merits a stop. Explore the museum’s carefully curated exhibits, which narrate the region’s fly-fishing heritage, local legends and lore.

Back in town is Dette Flies, Sullivan’s most iconic fly shop, which opened a new location in 2018 to commemorate 90 years of business. In addition to high-quality fishing gear, Dette’s offers lessons and guided excursions for anglers of every level.

Stay for lunch at Main Street Farm for soups, salads and sandwiches made with hyperlocal ingredients. Find veggies, cheeses and smoked trout from area producers in the adjacent marketplace, along with books, housewares and other goodies.

Narrowsburg NY at sunrise shot along the shores of the Delaware River in late November.

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Narrowsburg

Chic little Narrowsburg (20 minutes south of Callicoon) has long been a favored destination for New York City escapees on summer weekends. Named for its position overlooking the narrowest, deepest point of the Delaware River, the hamlet has only 340 residents but swells with innovative spirit. Along Main Street, visitors find quirky boutiques — Madam Fortuna peddles especially eccentric ephemera — an upscale wine shop and The Heron, one of Sullivan County’s best-loved farm-to-fork restaurants. Wander the galleries at the Delaware Valley Arts Alliance, which curates year-round exhibits of local and visiting artists.

The river is another draw, offering multiple ways to get on the water beyond casting a line. Since 1955, the folks at Lander’s River Trips have championed the pristine beauty of the Delaware, the longest free-flowing river in the eastern United States. For the ultimate experience, you can’t beat floating downstream in a raft on a summer day. Pack a cooler — Narrowsburg Proper, a “not so general general store” on Main Street, is a great place to gather picnic provisions. Add a bottle of wine from Narrowsburg Wine and Spirits or a growler of beer from a local brewery and you’re good to go.

If you’d rather a sit-down meal, tuck into inventive Neopolitan-style pizzas, lovely salads and delicious charcuterie at Launderette, a repurposed laundromat with a deck overlooking the Delaware River.

Bethel Woods Center for the Arts, concert hall, museum commemorating Woodstock Music Festival, Bethel, New York

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Bethel

Considering the big anniversary this year, you’ll want to detour about 12 miles south of Callicoon to Bethel. That’s where, in the winter of 1969, four young men decided to create a recording studio in the rural town of Woodstock. To raise money, they planned a large music festival for that August, yet it would be late July before they secured a location for the three-day event. That location was a 37-acre alfalfa field on the Bethel dairy farm of Max Yasgur.

That field became the site of the most famous music festival of all time. Today, along with hundreds of surrounding acres, it makes up the campus of the Bethel Woods Center for the Arts. Standing at the Woodstock monument, gazing out over the sloping bowl where nearly 450,000 people came together for three days of peace, mud and incomparable musical performances, is a semitranscendent experience whether you attended or simply wish you had.

Bethel Woods also houses a museum celebrating both the Woodstock Festival and 1960s America and an open-air performance pavilion, where several original Woodstock artists have appeared over the years. In honor of the 50th anniversary of Woodstock, a new exhibit, “We Are Golden,” features festival relics and examines youthful ambitions for positive societal change then and now.

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