View of the Delaware River and Callicoon from Seminary Hill. Photo: Daniel Schwartz
EB’s Top 5 in Callicoon:
• Sunday Mornings at the Callicoon Farmers Market: Open seasonally from late spring through early winter, this bustling market is a highlight of any visit. Wander among local vendors, stock up on fresh produce, and savor locally made provisions.
• Cider Flights at Seminary Hill: After a tour and tasting at Seminary Hill Cidery, head to The Tasting Room to sample a flight of their crisp, house-made ciders. Bonus: every seat overlooks Seminary’s orchards, providing a picturesque backdrop to enjoy while sipping.
• Wine and Tapas at Callicoon Wine Merchant: Part wine shop, part tapas bar, Callicoon Wine Merchant remains an Escape Brooklyn favorite. Begin with a simple cheese plate (we love anything covered in honey), then explore more substantial bites — and be sure to ask your server for pairing recommendations.
• River Rafting on the Delaware: During the summer months, make the short drive to Narrowsburg for a day on the Delaware River. Landers River Trips offers launches for rafting, kayaking, canoeing, and tubing, making it a versatile outdoor adventure near Callicoon.
• Black Walnut’s Craft Cocktails: Black Walnut’s cocktails strike a balance between thoughtful craft and unpretentious hospitality. Pull up a stool at the bar for a chat with the bartender, or settle into one of the cozy couches. Our current favorite drink: the Rhubarb Rosita, a mix of mezcal, honey, and rhubarb bitters.
Set along the banks of the Delaware River in Sullivan County, Callicoon blends river-town roots with a creative, slow-living spirit. Once a railroad and farming hub, the town has quietly evolved into one of the Western Catskills’ most inviting pockets — with vintage shops, natural wine bars, and farmers markets tucked between rolling hills and forested trails.
Whether you’re kayaking the Delaware, flipping through records downtown, or ending the day with oysters and pét-nat under string lights, Callicoon offers a weekend rhythm that’s both unhurried and inspired. Read on for our guide to what to do, eat, and drink in this character-rich Catskills town.
What to Do in Callicoon, NY: River Trips, Vintage Finds + Cider Tastings
The Delaware River, as seen from the Callicoon Bridge in town. Photo: Escape Brooklyn
Callicoon’s small-town charm is grounded by its walkable main street and riverside location. Shops here feel thoughtfully placed and easy to linger in. At Spruce, shelves are lined with pantry staples, housewares, and local ceramics in a space that leans more gallery than general store. Up the hill, Callicoon Vintage mixes retro furniture, vinyl, and 1970s oddities, ideal for collectors and vintage enthusiasts. Nearby, the Callicoon Marketplace houses several standout small businesses under one roof – from The Callicoon Pantry’s fresh produce and elevated provisions to house-milled breads at Roger That Bakery, and gluten-free sweets from Country Road Bakery. Timewarp Records is a must for music fans, with vinyl, tapes, CDs, and equipment. About 15 minutes outside town, the North Branch Cider Mill is a dreamy country store stocked with homewares, sweaters, and provisions — plus a friendly goat or two for photos and conversation.
Those interested in local libations can book tours and tastings at Seminary Hill, where crisp orchard ciders and a warm, hillside tasting room offer both refreshment and views of the river valley. For a low-key evening indoors, the Callicoon Theater — in operation since 1948 — screens new releases and indie films in a historic single-screen space with vintage charm. Come Sunday, the town’s open-air Farmers’ Market takes center stage; it’s one of the Catskills’ largest and best, with fresh produce, baked goods, and a steady crowd of locals and weekenders.
In summer, Callicoon’s location near the Delaware River makes it a convenient home base for getting on the water. Landers River Trips operates out of nearby Narrowsburg, about 15 minutes away, with rentals and routes for rafting, kayaking, canoeing, and tubing. It’s an easy way to spend a warm day outside — with gentle stretches of river, wooded scenery, and spots to pull over for a swim or picnic.
Where to Eat + Drink: The Best Bars and Restaurants in Callicoon, NY
Seminary Hill – a boutique hotel, working cidery, and restaurant – sits just beyond the center of Callicoon, framed by orchard-covered hills. Photo: Escape Brooklyn
Callicoon’s dining options highlight quality ingredients and local roots. For breakfast and lunch, Callicoon Caffè offers a straightforward, no-frills spot where fresh coffee pairs with simple, well-made dishes. Down the street, Navor Koken blends cafe and craft, with rotating pop-ups alongside German and Scandinavian-inspired fare, plus a curated selection of florals and handmade ceramics by local artists.
As the day winds down, Callicoon Wine Merchant doubles as a natural wine bar and bottle shop, pairing a thoughtfully rotating menu of light bites with carefully sourced bottles. Nearby, The Farmhouse Project’s Black Walnut serves seasonal small plates and mains in a quietly polished space, anchored by a cocktail program that balances creativity with restraint.
Where to Stay in Callicoon, NY: Boutique Hotels and Short Term Rentals
Less than 10 minutes from Callicoon, The Henderson offers a refined yet relaxed retreat that’s fit for groups large and small. Photo: Escape Brooklyn
Callicoon sits between the Western Catskills and the Delaware River Valley, balancing a rural, small-town feel with a growing spirit of creativity and hospitality. The town’s unpretentious, grounded atmosphere invites visitors to slow down and connect with orchard-lined hills, historic architecture, and a thriving community. Lodging options reflect that balance, offering a range of thoughtfully restored historic homes and design-forward getaways that provide comfortable, authentic bases for exploring the region.
A few standouts:
- The Henderson, a renovated Victorian with a pond, stone hot tub, outdoor shower, soaking tubs, and curated interiors;
- Seminary Hill, a boutique hotel, working cidery, and restaurant that overlooks the Delaware River Valley.
