How To Spend 48 Hours In Sullivan County

The Catskills Mountains revitalization continues with new hotels, restaurants, and drinking establishments blossoming across several counties. However, the best way to tackle this large, meandering region is in chunks. The 48-hour weekend works well, especially since most establishments are open for limited hours Thursday-Sunday anyway. (Welcome to life upstate!) For the first installment of 48-hours in the Catskills, I cover Sullivan County in the Western Catskills.

The key villages to visit include Livingston Manor, Roscoe, Callicoon, and Narrowsburg. On a map, the route between towns forms a lasso with Callicoon and Narrowsburg holding the figurative end of the rope. A 12-minute drive separates Livingston Manor from Roscoe, and a 25–30-minute drive separates both towns from Callicoon which sits south and west along the east side of the Delaware River. Narrowsburg, a charming hamlet founded in 1853, hugs the river another ten minutes south of Callicoon. Within this region, there’s lots to do both outside and in, even in winter.

Friday Afternoon Check-in, Dinner at the Hotel

Which hotel? Here are some options

One can’t go wrong booking a property in the fabulous Foster Supply Hospitality group’s local portfolio.  The 14 rooms at The Debruce run small but the hotel’s stylish common areas, as well as the first-rate, multi-course seasonal dining experience boasting one of the region’s best wine lists, make up for cozy digs. Eat, drink, and roll upstairs to bed.

The newer sister property, Kenoza Hall, also runs an elegant restaurant in a former 1880s summer boarding house. The 55-acre property features 22 guest rooms, many with Kenoza Lake views and large soaking tubs, plus snowshoeing outside the door for winter visits.

Just outside Livingston Manor, rural Arnold House has a fun vintage vibe. Have dinner in the old school tavern picking tunes out on the jukebox or hang in the greenhouse, admiring plants while sipping hot cider.

Callicoon Hills, the latest regional entrant, sits equidistant between Livingston Manor and Callicoon, making it a perfect base for tackling all four towns in a weekend. That said, after a dinner of New England shrimp rolls and friend chicken sandwiches paired with excellent cocktails at the Conover Club, one may be inclined to eat there twice in a weekend (we did!). Small rooms sans television, encourage guests to get outside to hike or lounge by the pool by day, and mingle at night. Fortunately, the hipster-friendly experience lacks the snootiness that often accompanies such projects in the Hudson Valley. Everyone is welcome at Callicoon Hills, making this a favorite pick for lodging. (No surprise, their motto is The Friendly Resort for Nice People.)

Saturday Morning

Head into Livingston Manor for two breakfasts. Sorry, but this is absolutely necessary. The first stop is Neon Croissant, co-owned by Lily Price and Erin Ellis, for the signature flaky pastry. While pricey, these extra buttery delicacies tie for best croissant in the Catskills (with Kingston Bread + Bar in Kingston.)

Next, head across the street for the best biscuit in the Catskills (no ties here), created by the same owners. The Walk In specializes in massive, fluffy mounds of buttermilk based on a fourth-generation recipe from Lily Price’s southern great grandmother. The breakfast sandwiches should be shared, especially when piled high with eggs, cheddar, and sausage.  

Walk off a few calories with a stroll down Main Street. Shops to explore include Nest for global home furnishings curated by Danish-Brazilian designer Anna Bern, Dear for women’s clothes and accessories, Concrete + Water for independent designers plus colorful textiles and dinner plates. Find vintage housewares and furniture at Taylor + Ace. Main Street Farm specializes in local produce, provisions like beer and cider, plus regionally inspired sandwiches to-go for hikes or picnics. Grab a bottle of biodynamic natural wine from Upstream Wine + Spirits or return in the afternoon/evening for a glass at related wine bar, Sunshine Colony.

Saturday Afternoon

Depart Livingston Manor for Callicoon. On the way out, take a short detour to Upward Brewing, located off Main Street just out of town. One of upstate New York’s most design-forward breweries that also has a fantastic hazy IPA-heavy beer list, the black steel exterior juxtaposes against warm wood tones of the interior. Mid-century modern décor and a large fireplace framed in glazed tiles encourage lingering. While the food is good, save your stomach for Callicoon.

Arrive at Catskill Provisions for a tasting with lunch. Owners Claire M Marin and her partner Cathy Leidersdorff focus on farm-to-glass spirits with New York ingredients. Local organic honey and rye, for example, form the base of their award-winning rye whiskey. Try it in a flight or in a jalapeno margarita; order the pulled pork sandwich with corn bread to soak everything up.

Stroll the streets of Callicoon. Bisected by train tracks, this small town maintains the country throwback vibe of its founding era in 1842. If you catch one shop, make it Spruce Home Goods for everything from glassware, bedding, to cheese and prepared foods.

Saturday Evening

To check out Roscoe, book dinner at The Junction. Creative tipples and comfort food using regional ingredients like trout, speak to owners’ Misty Hackworth and Aaron Blakely experience in Brooklyn hospitality. The sportsman’s dive bar vibe blended with vintage décor feels both retro and modern. During summer, daily frozen drink specials feature fruit from nearby farms.

Another option near Roscoe is Northern Farmhouse Pasta. Either pick up pasta to take home, made from 100% New York grown wheat, or book a dinner reservation. Sample classic Italian dishes like tagliatelle bolognese, order the local spin on piccata using trout, or slurp up bowls of ramen, a chef favorite because noodles.

In the opposite direction, Cochecton restaurant Henning’s Local has earned rave reviews for its surprising middle-of-nowhere culinary prowess. Norwegian chef Henning Nordanger offers his take on American comfort food, featuring, of course, trout multiple ways (look out for Beaverkill trout sashimi) as well as local beef, lamb, and chicken.

The newest weekend hot spot in Sullivan County, or at least what counts as such a thing in the Catskills, is the Cochecton Pump House. Food trucks provide sustenance to revelers who descend for live music and local beers served inside the red brick shell of an abandoned 1879 oil pump station.  

Sunday Morning

Depending on the season, spend Sunday morning outdoors. Try fly-fishing the county’s famous trout-rich streams and rivers. Dette Flies in Livingston Manor has helped neophytes and professionals with gear and suggestions since 1928.

Hikers will appreciate the deciduous fall foliage of Walnut Mountain Park and Willowemoc Wild Forest. Photogs bring gear to Bouchoux Trailhead for the famous (locally, anyway) Jensen’s Ledges. A short but steep hike yields thrilling panoramic views of the Upper Delaware River Valley.

Kayakers and water babies eager to enjoy the river can book scenic floats down the Delaware through Lander’s River Trips.

Sunday Afternoon

Tiny Narrowsburg is crammed with shops and restaurants, but only requires an hour or two to canvas. Try the Heron for lunch, one of the village’s first restaurants with gastronomic ambition. (Always check the status of any restaurant in town before committing. Many are short-staffed and have closed, reduced hours, or doing take-out only.)

Alternatively, visit Launderette for crunchy wood-fired sourdough pizzas with river views. Don’t miss the luscious honey-based ice creams by B Line. Flavors range from original to cardamom pistachio and Mayan chocolate.