120 miles from NYC, Seminary Hill is many things: an orchard, with more than more than 60 varieties and 1,500 trees on 12 acres; an eco-friendly cidery meeting PassivHaus standards; a tasting room and restaurant where ciders are paired with fresh, local food; and an enchanting boutique hotel, with 17 units across eight apartments.

Proudly local and sustainable, Seminary Hill’s cidery and tasting room is perched atop one of the highest hills in Callicoon, NY. Its picturesque views overlook the former St. Joseph’s seminary, the Delaware River, and nearby Pennsylvania — the combination of which makes for a most spectacular setting to grab a drink or bite while watching the sunset. The ciders are delicious and complex; all lean toward the drier (read: crisper and better) side of the spectrum.

Should you get carried away drinking in all the fun, just down the hill from the orchard and closer to town, Seminary Hill’s Boarding House is the perfect spot to call home for the weekend. Seventeen rooms are housed across eight apartments in two buildings one a former hospital from the 1930’s, and the other a doctor’s office from the 1870’s. The buildings were renovated under the direction of local design studio Homestedt, whose Shaker-inspired vision for the Boarding House means simple yet chic, totally cozy rooms each with private bathrooms, many with restored vintage claw foot tubs, and all with complimentary luxury bath amenities. Like the boarding houses of old, there are some shared spaces for guests, including the lobby/living room stocked with books and cozy couches, and a kitchen where guests are welcome to cook themselves a meal, or enjoy the breakfast buffet. Should you fall in love with the vibe and you will design studio Homestedt’s nearby shop is filled with many of the housewares, sheets, and toiletries you’ll find at Seminary Hill Boarding House.

Ready to plan a trip? Read on for our recommendations, including what to do in Callicoon, NY — from where to shop, hike, and get outside – plus the best places to eat or grab a drink.

What to Do: Shopping and Exploring the Delaware River town of Callicoon, NY

The historic Callicoon Theater, which is listed on National Historic Registry, hosts one screen, 350 seats, a decked out surround sound system and a fully upgraded digital projection system for a quality viewing experience. Photo: Jerry Cohen.

As of late, it could be argued that this Delaware River town is the liveliest of them all. With the cidery, a distillery, a gem of a movie theater, excellent shopping, the region’s most esteemed farmers’ market (on Sundays), plus its own natural wine shop and bar there’s plenty to do.

Along Main Street, Callicoon’s main thoroughfare (split into Upper and Lower Main Street) visitors will find a great selection of places to shop and enjoy. Visit the many antique shops in town, including the aptly named Antique Center for an eclectic inventory of furniture, lighting, art and other home accessories. At Ragtime Clothing Exchange, you’ll find a collection of vintage clothes and other curiosities. Audiophiles can flip through records at Time Warp, then make their way over to Callicoon Marketplace, a community space that hosts both permanent businesses and rotating pop-ups year round. Litt Home and Book deserves a mention, as well as Spruce Home Goods, which boasts a fantastic selection of gourmet foods including cheeses, breads and local eggs but also premium goods for the home, including table wares, bedding, home fragrance and more.

Whether you’re making a weekend of it, or just stopping through town, check out Seminary Hill on Saturdays for a tour that ends with a guided tasting of their inventive ciders. Tours start at 11 am and cost $48 per person ($20 for those 13-20 years of age, free for kids 12 and under).

No rainy (or sunny) day is boring in Callicoon with the option of seeing a movie at Callicoon Theater, who’s big on charm, nostalgia, and of course, movies. The theater, which is listed on National Historic Registry, hosts 350 seats, a decked out surround sound system and a fully upgraded digital projection system for a quality viewing experience. (Of note: they also use real butter on their popcorn!) A single screen means that movies come and go quickly – check their calendar to scope what’s playing.

Get Outside: Float the Delaware River & Hit the Trails on the Best Hikes Near Callicoon, NY

A misty summer sunrise over the Delaware River in New York. Take the scenery in by boat, tube, or hike to a nearby overlook.

Callicoon first got its name from Dutch colonizers who settled in the region during the 17th Century, calling it “Kollikoonkill” which translates to “Wild Turkey Creek.” Beyond wild turkeys, the town is also known for its eagle watching and other vast array of wildlife.

Nestled in the foothills of the Catskill Mountains, Callicoon sits along the banks of the mighty Delaware River, and there’s no shortage of opportunities to take advantage of this region’s natural splendor. Visit Soaring Eagle River Trips, Lander’s River Trips or Kittatinny Canoes to book a seasonal outdoor adventure, spending the day canoeing, kayaking or tubing along the Delaware. We love Soaring Eagle’s trip launching from Long Eddy, taking about 2.5 hours to get downriver.

For those wanting to stretch their legs, the most popular trail in the region is the 3 mile Tusten Mountain Trail, which climbs through the forest to an overlook of the Delaware River. Jensen Ledges offers a similar experience: a 3 mile trail, whose trailhead begins a bit further from Callicoon — but gives way to much more dramatic views, including a scenic waterfall at the top. Last, for a more casual afternoon jaunt, River Road right in Callicoon is a convenient spot for a stroll to drink in the scenery of the Delaware River, year-round.

Eating & Drinking: the Best Restaurants, Bars and More in Callicoon, NY

Seminary Hill’s Tasting Room has phenomenal views of the Delaware River Valley; it’s the perfect spot for a sunset drink or meal.

Guests fortunate enough to be staying at the Boarding House at Seminary Hill are provided a continental breakfast on weekends, including fruit, freshly baked breads and pastries, yogurt, granola, hard boiled eggs, juice, milk, and fresh coffee. When you’re ready to venture out, we got you.

If you’re feeling indulgent, head down to our new favorite spot in town – Grizzly Bagels – whose mouth-watering offerings sell out quickly on weekends, and for good reason. At the risk of upsetting people, we’re going to go ahead and put this on record: they’re better than city bagels. Try the delightful cheddar jalapeño bagels for a savory treat.

For lunch or dinner, grab a bite (or many) at the Seminary Hill Tasting Room, whose thoughtfully curated menu of mains and snacks are inspired by the local region. It’s open for dinner Thursday-Sunday, and lunch on weekends. Also notable: on Thursday, the Tasting Room offers a BBQ menu, serving family-style dinners of southern dishes including fried chicken, pulled pork and traditional sides.

Just outside town, we also love Cochecton Fire Station for lunch or dinner, housed in a former fire station. Their food menu, inspired by the wood-burning oven that sits at the heart of the establishment, embraces classic American fare think mac and cheese, hasselback potatoes, artichoke dip and s’mores; flavors enhanced by open flames. Pair your plates with one of their delicious cocktails standouts include the Queen’s Park Swizzle, Hook & Ladder Punch and Barren Mary (their unique take on the Bloody). Hikers take note: it’s on the way to the Tusten Mountain Trail from Callicoon.

Back in Callicoon, a few local spots are sure to hit the spot. The Creek House Grill promises solid fare redolent of an Irish pub. During the warmer months, Ollie Grey’s is a take-out spot perfect for summer days & nights spent outside, serving ice cream, tacos, falafels and more. Overlooking Upper Main Street, Catskill Provisions is a farm gastro-distillery, tasting room and restaurant, offering up fun craft cocktails and bistro fare.

Last, our favorite nighttime spot in town is Callicoon Wine Merchant, where guests enjoy an impressive selection of natural wines and tapas. Their outdoor space can be enjoyed during warmer months, or in winter, pull up a seat at the cozy bar inside; it’s the perfect place to hang for any occasion, be it date night, or a casual hang with friends.