The Best of Callicoon, NY
Callicoon, New York, is where countryside charm meets creative flair. Perched on the banks of the Delaware River, this Catskills town buzzes with indie shops, delicious eats, and a warm community feel that keeps visitors coming back. We’re spotlighting 32 standout spots that showcase everything we love about this little river town. Whether you’re planning a weekend away or a leisurely day trip, Callicoon is calling. Time to plan your escape.
1. Callicoon Theater
📍Location: 30 Upper Main St, Callicoon, NY
Callicoon Theater is the oldest continually operating movie theater in the Catskills, and somehow it still feels like a hidden gem. With indie flicks, vintage seats, and a glowing marquee, it’s pure small-town movie magic. Grab some popcorn and lean into the charm.
2. Pollinator Spirits
📍Location: 20 Dorrer Dr, Callicoon, NY
Tucked in a hillside barn, Pollinator Spirits distills small-batch gin, vodka, and more using locally sourced botanicals. It’s warm, earthy, and a little bit wild. Stop by the tasting room to sip something unexpected and beautifully balanced.
3. Upward Brewing Co.
📍Location: 15 Lower Main St, Callicoon, NY
Upward Brewing Co. combines stellar craft beers with panoramic mountain views. The taproom has a cool, laid-back energy and the trails out back are perfect for a pre- or post-pint hike. Don’t miss the “Elevation” IPA…it lives up to the name.
4. One Grand Books
📍Location: 43 Wagner Ln, Callicoon, NY
One Grand Books is a cozy literary outpost with a unique twist—every title is handpicked by tastemakers, artists, and writers. The shop is small but mighty, and full of great surprises. If you love books with a backstory, this is your place.
5. Callicoon Wine Merchant
📍Location: 49 Wagner Ln, Callicoon, NY
Callicoon Wine Merchant keeps things low-intervention and high quality with a sharp selection of natural and organic wines. The space doubles as a wine bar, so you can sip before you commit. Staff picks are always spot-on.
6. Seminary Hill
📍Location: 49 Seminary Rd, Callicoon, NY
Seminary Hill is a hilltop cidery with sweeping views and seriously good cider. From dry to aromatic, each pour reflects the orchard it came from. Stick around for a tasting flight on the deck—you won’t want to leave.
7. Nest Catskills
📍Location: 10 Upper Main St, Callicoon, NY
Nest Catskills is part design shop, part home inspiration wonderland. From linens to lighting, everything here feels curated and calm. Come in for a candle, leave dreaming about a whole new living room.
8. The DeBruce
📍Location: 982 Debruce Rd, Livingston Manor, NY
Dining at The DeBruce feels like being let in on a delicious secret. With a hyper-local tasting menu and sweeping valley views, it’s a culinary experience wrapped in Catskills beauty. Book ahead—it’s special occasion territory for a reason.
9. Old Souls NY
📍Location: 44 Upper Main St, Callicoon, NY
Old Souls NY is a rustic-meets-modern general store with a little bit of everything: fly fishing gear, heritage clothing, outdoor essentials, and hard-to-find local goods. It’s a great place to stock up before hitting the trails—or just browse with a coffee in hand.
10. Sunshine Colony
📍Location: 35 Lower Main St, Callicoon, NY
Sunshine Colony is a cocktail bar with cozy indoor vibes and a sun-drenched patio out back. The drinks are creative without being fussy, and the snacks hit just right. It’s the kind of place where one round turns into two.
11. Buck Brook Alpacas
📍Location: 1030 Old Rte 17, Livingston Manor, NY
Buck Brook Alpacas is a wholesome detour where you can meet, feed, and even walk with a herd of curious, fluffy alpacas. Great for kids, better for your camera roll, and guaranteed to make you smile. Don’t forget to check out the farm shop on your way out.
12. Catskills Curated
📍Location: 23 Dorrer Dr, Callicoon, NY
Catskills Curated lives up to its name with artisan-made goods, from hand-poured candles to farm-sourced snacks and pottery. It’s the kind of place where gifting yourself is totally justified. Everything feels thoughtful, useful, and a little luxurious.
13. Homestedt
📍Location: 31 Lower Main St, Callicoon, NY
Homestedt blends Scandinavian design with upstate sensibility. You’ll find wool blankets, handmade soaps, and beautifully understated homewares.
14. J Ville Bake Shop
📍Location: 30 Lower Main St, Callicoon, NY
J Ville Bake Shop brings serious pastry game to the heart of town. From buttery croissants to gooey cinnamon rolls, everything is baked with love and a little extra flair. Come early or risk missing your favorite.
15. Catskill Fly Fishing Museum
📍Location: 1031 Old Rte 17, Livingston Manor, NY
The Catskill Fly Fishing Museum is a hidden gem for anyone drawn to rivers and rods. Explore vintage gear, learn about fly-tying history, and get inspired by the Catskills’ legacy as a fishing haven. It’s unexpectedly fascinating—even if you’ve never held a reel.
Whether you came for the small-town charm, riverside views, or unexpected gems tucked along Main Street, Callicoon has a way of leaving a lasting impression. It’s the kind of place that invites you to slow down, stay a little longer, and start planning your next visit before you’ve even left. Book your Red Cottage Callicoon getaway today.
