A Winter Wine & Cider Getaway in New York’s Sullivan Catskills

Seminary Hill Orchard & Cidery

If you only have time for one stop in the area, make it Seminary Hill. Between the cidery, the restaurant, and the nearby Boarding House, this is the kind of place you could build a whole weekend around.

It’s also the world’s first cidery built to Passive House standards, which basically means it’s designed to use way less energy. And natural and reclaimed materials are used throughout, like wood from the old Tappan Zee Bridge.

The experience feels closer to visiting a modern winery than a typical cider stop. Our tour, led by cidermaker Joshua Hinchman, took us through the orchards and production space, where we learned how they use dozens of apple varieties to create more complex, wine-style ciders. He explained that the “uglier” fruit makes better cider. And they even hold back bottles to see how they evolve over time.

After the tour, we headed upstairs to the tasting room, where huge windows overlook the orchard and the Delaware River Valley. Even on a winter day, it felt warm and inviting. We sampled six ciders with generous pours. I was surprised at how different each tasted, from dry and still to off-dry and sparkling to fortified, dessert-style ciders.

Seminary Hill Orchard & Cidery, 43 Wagner Ln, Callicoon, NY

Just off Main Street along the river, Callicoon Wine Merchant feels like the kind of place you stumble upon and end up staying all evening.

Owner and chef Robin Mailey left the NYC restaurant world for the Catskills, seeking a quieter life. And it shows in both the exceptional food and the relaxed, slightly après-ski vibe. In winter, you can hang with the locals at the bar, while summer brings a lively patio crowd.

Grabbing a seat at the bar, I quickly realized you can’t go wrong here. The wine list is refreshingly offbeat, with options like Txakoli and Grillo. But the food absolutely stole the show. The smoked trout salad, salt cod croquettes, and a tender pork dish with a savory, slightly sweet kick were all dishes I’d happily order again.

Callicoon Wine Merchant, 30 A Dorrer Dr, Callicoon, NY

Down the road in Livingston Manor, Sunshine Colony is a natural wine bar with a casual, welcoming feel. In warmer months, the back patio is a big draw, but in winter it turns into a snug little hideaway. There’s bar seating up front, plus a separate room with low tables and pillow-lined benches that make you want to settle in for a while.

The list focuses on natural wines, but they also have craft beer, cocktails, and a small snack menu if you want something to go with your drinks.

We ordered a Lambrusco for me and a Manhattan for my husband (because when in New York), then grabbed a seat in a cushioned nook. It was the perfect place for a pre-dinner drink after a day of exploring.

Sunshine Colony, 47 Main St, Livingston Manor, NY

Just down the street from Sunshine Colony in Livingston Manor, Upstream Wine & Spirits is a thoughtfully curated shop focused on sustainable, organic, and biodynamic bottles.

They occasionally host weekend tastings, but it’s just as good for browsing shelves full of interesting finds from smaller producers.

We stopped in to browse, and I ended up snagging a bottle from one of my favorite Santorini wineries, which immediately earned this place bonus points. It’s a great stop to grab something special to enjoy back at your hotel after dinner.

Upstream Wine & Spirits, 65 Main St, Livingston Manor, NY

Located in the same space where we did our cider tasting, The Tasting Room at Seminary Hill comes with views only rivaled by the food. Floor-to-ceiling windows look out over the orchard, the old seminary tower, and the Delaware River Valley.

They serve brunch and dinner on weekends along with their full cider menu. The drinks list also includes local New York wines like Benmarl from the Hudson Valley and Dr. Konstantin Frank from the Finger Lakes.

We ordered glasses of cider with our meal, and I went straight for my favorite from the tasting, Delaware Dry, which paired well across courses.

The fried chicken skins are a must. They’re ridiculously crispy and perfect with the buttermilk dipping sauce. My salmon with melted leeks practically melted in my mouth. And I stole a few bites of my husband’s duck breast with cranberry and endive, which was just as satisfying. Dessert was a cider posset, an orchard-inspired ending that I didn’t know I was missing in my life.

My husband and I both agreed this was one of the best dinners we’ve had in a while.

Seminary Hill Orchard & Cidery, 43 Wagner Ln, Callicoon, NY

Right on Main Street in Callicoon, Black Walnut feels like a chic spot you’d find in a city, not a small river town. It’s set inside the former Delaware Hotel and has a little bit of everything. There’s a boutique shop in front selling handmade home goods, an elegant cocktail lounge in the back, and the restaurant tucked off to the side with rich green walls, tin ceilings, and long velvet bench seating.

The owners relocated from NYC and teamed up with Executive Chef and Co-Owner Camille Rodriguez to bring creative cooking to a space with plenty of personality. The wine list reads mostly international, with a few New York bottles in the mix, making it a great pick for wine lovers.

Dinner here completely delivered. The East Coast oysters were bright and fresh, and the charred Brussels sprouts had that perfect salty-savory balance that makes you keep reaching for another bite. My rigatoni with beef and porcini ragu hit the spot on a cold night, and the roasted chicken came out juicy with perfectly crisp skin.

After dessert, the meal finished with a digestif of their very own black walnut liqueur, made from the trees on their property.

Black Walnut, 39 Lower Main St, Callicoon, NY

Things to Do Between Tastings

Between meals and tastings, there’s plenty to explore in the Sullivan Catskills, from music history to small-town shopping and wandering the river towns nearby.

Bethel Woods Center for the Arts

About 20 minutes from Callicoon, Bethel Woods Center for the Arts is both a major concert venue and the site of the original 1969 Woodstock Music & Art Fair.

The big outdoor shows happen in summer, but there’s also a smaller indoor performance hall with events year-round, so it’s worth checking the schedule even on a winter trip.

Fun fact: my dad was at Woodstock. I grew up hearing how he and his friends got stuck in traffic, stayed overnight with locals, and then caught a ride with a police officer who dropped them right at the front of the stage. It was pretty surreal to finally see the place I’d heard about in all those stories.

The museum is easy to spend a couple of hours in. It walks through the history, planning, and happenings at the festival and includes cool artifacts like instruments, outfits, and even a giant VW bus you can step inside. The 360-degree screening room was a highlight. Afterward, we drove down to the monument at the edge of the field where the festival took place.

Bethel Woods Center for the Arts, 200 Hurd Rd, Bethel, NY

One of the best winter activities in the Sullivan Catskills is simply wandering the nearby small towns. If you’re staying in Callicoon, there are several just a short drive away.

North Branch

Just 10 minutes away, North Branch is home to the beautifully restored North Branch Cider Mill, a former cidery turned general store. The moment I stepped inside, I was hit with the most amazing scent and immediately had to hunt down the candle responsible. It was hard not to go overboard, with shelves of tempting pantry goods and gifts. I somehow showed restraint, but still left with homemade pickles and chocolate chunk cookies.

Livingston Manor

About 25 minutes from Callicoon, Livingston Manor is often called the Brooklyn of the Catskills thanks to its mix of creative shops, bars, breweries, and restaurants. This is where we visited Sunshine Colony and Upstream Wine & Spirits, then popped into a few boutiques before warming up with a hot drink at one of the town’s cozy coffee shops. You can easily spend an afternoon just browsing and wandering.

Narrowsburg

Roughly 15 minutes away, Narrowsburg is another popular river town known for its restaurants, galleries, and shops. We didn’t have time to visit on this trip, but it’s often recommended as one of the best towns in the area if you’re looking to add another stop to your weekend.