You’ve probably seen the glossy brochures of the Catskills. They show pristine lakes, high-end yoga retreats, and people in expensive flannels holding artisanal cider. Honestly, if that's all you think is out here, you're missing the point. Sullivan County isn't just a weekend escape for New Yorkers looking to "find themselves" in a forest; it’s a weird, beautiful, and sometimes gritty collection of hamlets where history feels incredibly close to the surface.
Sullivan County has always been a place of reinvention. From the "Borscht Belt" glory days of the 1950s to the legendary mud of 1969, this region has a habit of hosting the world and then retreating back into the woods.
People ask me all the time about the best things to do in Sullivan County NY, and they usually expect me to just say "go to Bethel Woods." Don’t get me wrong—you should absolutely go there—but there is so much more to this county than a single (albeit historic) field.
The Bethel Woods Factor: More Than Just Ghostly Hippies
Bethel Woods Center for the Arts is the obvious heavy hitter. It’s sitting right on the hallowed ground where the 1969 Woodstock festival went down. But here is the thing: most people just walk through the museum, see the tie-dye, and leave.
If you're visiting in 2026, you need to check the event calendar for the smaller, more intimate stuff. While the 15,000-seat amphitheater pulls in names like James Taylor (set for June 18, 2026) and Joe Bonamassa, the Event Gallery and Museum Theater are where the real magic happens.
For instance, this spring, they’re running a "Winter Wellness" series that’s actually pretty cool—think figure drawing with Jorge Colombo or "Rock Band Jams" for adults who never gave up on their garage band dreams. In March 2026, keep an eye out for "All You Need is George," a massive celebration of George Harrison.
Pro Tip: If you’re going for a big summer concert, don't just drive in and out. The Museum at Bethel Woods has an outdoor "Binds the Generations" exhibit that hits different when the sun starts setting over those rolling hills.
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Getting Your Feet Wet (Literally)
If you aren't a "museum person," you probably came here for the water. The Upper Delaware Scenic and Recreational River is the lifeblood of the western side of the county.
Narrowsburg and Callicoon are the gateways here. You’ve got options. You can rent a tube, kick back, and let the current do the work while you look for bald eagles. Or, you can take it seriously.
Roscoe, famously known as "Trout Town, USA," is where fly fishing isn't a hobby—it's a religion. The Beaver Kill and Willowemoc Creek meet here at Junction Pool. Legend has it the fish are so smart here they recognize specific brands of lures. If you're a novice, stop by Dette Flies. It’s the oldest family-owned fly shop in the country, and the folks there will actually talk to you without being condescending about your lack of technique.
Hiking the Neversink and Beyond
The Neversink River Unique Area is where you go when you want to disappear for a few hours. It’s 6,580 acres of gorge, waterfalls, and silence.
The hike to Mullet Brook Falls is a local favorite for a reason. You start at the Katrina Falls trailhead. It’s a bit of a trek—about 2.8 miles round trip—but you end up at a waterfall tucked behind a "tunnel" of rhododendrons. It feels like something out of a fantasy novel.
If you want views without the vertical struggle, the O&W Rail Trail is your best bet. It’s an old railway bed turned into a multi-use path. The Hurleyville segment is particularly great because it’s paved and ADA-compliant, making it accessible for everyone from serious cyclists to parents pushing strollers.
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The "Good Taste" Trail: Where to Eat and Drink
Sullivan County's food scene has exploded lately, but it hasn't lost its soul. We call it the "Good Taste Beverage Trail."
Livingston Manor is basically the craft beer capital of the county right now. Upward Brewing Company sits at the base of "Beer Mountain" (yes, you can hike it). Their Breadwinner IPA is a staple. Then you have Catskill Brewery, which is housed in a sustainable, gold-certified LEED building. Try the Devil’s Path IPA—it’s named after a notoriously difficult hiking trail, but the beer is much easier to swallow.
In Roscoe, the Roscoe Beer Co. is the place to be on a Saturday afternoon. It’s located in a former firehouse and feels like a community living room.
Food-wise, you’ve got to navigate the "Taste of Sullivan" participants.
- The Roscoe Diner: It’s an institution. You don’t go for gourmet; you go for the oversized menus and the feeling of 1970s nostalgia.
- 2 Queens Coffee (Narrowsburg): Small-batch roasters who take their beans very seriously.
- The North Branch Inn: If you want something upscale. They have a two-lane vintage bowling alley in the back that still uses manual pin-setters.
Small Towns with Big Personalities
Every town in Sullivan has a different "vibe."
Narrowsburg is the "cool kid." It’s perched right on the Delaware River and is packed with galleries and boutiques like One Grand Books, where they organize books by the recommendations of famous people.
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Callicoon is a bit more laid back. The Callicoon Theater is a single-screen cinema from 1948 that still feels like a time capsule. They play one movie at a time, usually something worth seeing. On Sundays, the Callicoon Farmers’ Market is non-negotiable. It’s where you’ll find the best local cheeses and sourdough.
Liberty and Monticello are the busier hubs. If you're looking for modern entertainment, Resorts World Catskills in Monticello is a massive casino and resort. It’s a stark contrast to the quiet woods, but if you want high-stakes poker and a luxury spa, it’s there. Right next door is The Kartrite, which is New York’s largest indoor waterpark. It’s 84 degrees in there year-round, which is a lifesaver in February.
What Most People Get Wrong
The biggest mistake? Treating Sullivan County like a theme park.
This isn't a curated experience where everything is open 24/7. Many of the best spots—especially the farm-to-table restaurants in towns like Jeffersonville or Cochecton—might only be open Thursday through Sunday.
Also, cell service is... optimistic. You will lose GPS. You will end up on a dirt road that looks like a driveway. That is part of the charm.
Actionable Next Steps for Your Trip
- Download Offline Maps: Seriously. Before you leave Monticello or Liberty, make sure your Google Maps is downloaded for the whole county.
- Check the "Catskills Beverage Trail" App: Most of the breweries and distilleries (like Do Good Spirits in Roscoe) offer a "passport" that gets you discounts.
- Book Dinner Early: If you’re eyeing a spot like The Cabin in Jeffersonville or Sorella Pizza by Kauneonga Lake, call ahead. In 2026, the local food scene is busier than ever, and "squeezing you in" isn't really a thing on Saturday nights.
- Pack for "Catskill Layers": It can be 75 degrees in the sun and 50 degrees as soon as you step into the shade of the hemlocks.
Sullivan County is a place where you can spend $500 on a tasting menu or $0 sitting by a river watching the water move. Both are equally valid ways to spend your time here. The key is to stop trying to see "everything" and just pick a town, find a trail, and see where you end up.