Introduction
When I first visited Callicoon, New York, I honestly didn’t know what to expect. Nestled along the banks of the Delaware River, with the Catskills rising all around, it seemed like a quiet little out-of-the-way town. But what I discovered over a weekend was a charming blend of nature, history, local flavour and small-town culture. Whether you’re after fresh air on the river, quirky shopping, local eats, or just a relaxing escape, Callicoon offers more than meets the eye. Here are 12 of the best & fun things to do in Callicoon, NY, drawn from my personal visits, discoveries, and unexpected delights.
12 Best & Fun Things To Do In Callicoon, NY (2026)
1. Hit the Water: Kayaking, Tubing & Canoeing on the Delaware
One of the biggest “aha” moments for me was realising how easy it is to get on the water. Callicoon sits right on the banks of the Delaware River, and the local tourism site spells it out: “kayaking, canoeing, rafting, tubing, swimming and fishing” are all available. I went with a float trip in summer—and the river trip, marked by leafy banks and shimmering currents, gave the whole place a relaxed, carefree feel.
Tip: Bring a change of clothes (you will get wet), some waterproof sandals and check access points along Route 52 and 17B where you can launch.
See Also: 12 Best Fun Things To Do & Places To Visit In Wisconsin
2. Sunday at the Farmers’ Market
There’s something really grounding about a good farmers’ market—and the Callicoon Farmers’ Market ticks that box. Held year-round on Sundays, it features local farms, baked goods, maple syrup, artisan crafts and that friendly community vibe. During my visit I grabbed fresh produce, chatted with a honey-producer and just soaked in the sunny morning buzz.
Tip: Go early—11 am opening means prime picks and good parking early in the day.
3. Wander Main Street & Explore the Local Shops
One afternoon I strolled through the heart of town and found a cluster of charming shops—vintage furniture, quirky home goods, artisan wares and cafés. As one guide puts it: “shops here feel thoughtfully placed and easy to linger in.” I was drawn to a store of curated ceramics and another of retro vinyl records.
Tip: Budget some time for “window-shopping” because you’ll find treasures in unexpected corners.
4. Catch a Show or Film at the Historic Callicoon Theater
For a low-key evening treat, I visited the Callicoon Theater, a single-screen vintage movie house from 1948 that still screens films and hosts events. The nostalgic ambiance made the night feel special—think polished wood, old-school décor and a communal, comfortable vibe.
Tip: Check ahead for film schedules or special music nights—they sometimes host live performances too.
5. Sip Local Taps & Ciders: Seminary Hill Cidery + Callicoon Brewing
As evening rolled in, I headed to a tasting room perched above town — the Seminary Hill Orchard & Cidery — where I sampled small-batch ciders with a view. Nearby, the local brewery scene (Callicoon Brewing Company) and wine bars add further options for winds-down. It was a great contrast to daytime activity—a relaxed sip with scenery.
Tip: Book a tasting or head in before sunset to enjoy golden light on the valley from the deck.
6. Follow the Historic Trail: Erie Railroad Depot & the Callicoon Bridge
I love a bit of history mixed with scenic views. Callicoon provides that with the old railroad station being repurposed (the Callicoon Depot) and the Callicoon Bridge crossing the Delaware offering a photo-worthy moment. The bridge gives you a literal “cross-the-state-line” span (NY ↔ PA) and sweeping views of the river valley.
Tip: Head to the river bank near Bridge Street in the late afternoon for good light and reflection shots.
7. Hike & Bike the Country Roads and Trails
For fresh air I found a lesser-known but deeply rewarding part—exploring the back roads, small trails and waterways around Callicoon. The tourism site notes: “magnificent sunrises, sunsets and Catskill fall foliage while walking, biking, hiking or driving on our beautiful back roads.” I rented a bike locally, followed a winding road through woods and fields, and capped it with a river-side walk.
Tip: If you visit in fall, bring a camera—leaf-change in the valley is stunning around late September.
8. Dine Locally: Cozy Cafés, Tapas & Farm-to-Table Finds
During my trip I made a point to check out local food spots—and I was delighted. From a charming café to a tapas-wine bar and hearty local fare, Callicoon has more depth than I’d assumed. A recent profile highlights the drink & food scene as “one of the best in Sullivan.” One morning I had a leisurely latte and pastry; another evening I savoured a glass of cider with locally-sourced cheese.
Tip: Dinner reservations recommended on weekends; check hours in the off-season as some places scale back.
9. Antique Hunting & Vintage Finds
If you’re into quirky finds or vintage treasures, this little town will surprise you. One guide highlights stores full of retro furniture, vinyl, 70s oddities and even artisan goods. I spent an hour in one boutique digging through old records and another browsing handmade home-wares.
Tip: Bring space in your vehicle—those finds can be tempting to bring home!
10. Participate in a Seasonal Festival or Event
One of the loveliest surprises was discovering the community events. For example, the “Dickens on the Delaware” holiday celebration brings Victorian-style festivities, and there’s also the annual tractor parade (lots of community fun). I happened to visit on a weekend when there was a craft fair in town and it added a lot of energy to what might otherwise have been a “quiet” afternoon.
Tip: Check the town’s events calendar in advance to time your visit with something fun.
11. Wildlife Watching & Fishing Along the River
I found a quieter side of Callicoon by simply being still. The region promotes eagle watching, fishing, and observing wildlife along the Upper Delaware valley. I sat by a river-bank and watched birds glide overhead, enjoyed the rippling water and felt a sense of calm away from the more touristy spots.
Tip: Bring binoculars if you have them; dawn or early morning often gives you the best light and fewer people.
12. Stay in & Enjoy a Unique Inn or Cottage Escape
Finally, after a busy day I appreciated having a comfortable place to stay. There are boutique inns and cozy accommodations that lean into the laid-back, nature-adventure spirit of the region. One mention of the Inn at Tyler Hill has a local-area overview of Callicoon’s dining and nature spots. Staying overnight meant I could stretch my schedule past just the daytime hits into evening wandering, river views and waking to quiet mornings.
Tip: Book ahead for weekends, especially in peak foliage season (late Sept to early Oct).
Final Thoughts
My time in Callicoon, New York, turned out to be richer and more memorable than I’d expected. I went in thinking it would be “a quiet town by a river” and I left with a sense of place: somewhere that blends natural beauty, local culture, interesting food, and that beloved small-town energy. From floating down the Delaware to browsing vintage shops, sipping cider with a view, or simply watching eagles above the trees, there’s a lot to savour.
If I were to pick a couple of my favorite moments: one was watching the sun dip behind the hillside while sipping a cider at Seminary Hill; another was the slow bike ride on a tree-lined road, free from noise and traffic. But I also loved the bustling Sunday market and a spontaneous movie night at the old theater.
If you’re planning a visit, consider a long weekend rather than just a day trip—there’s enough variety here to fill two or three days without feeling rushed. Allow time for unplanned stops (that vintage shop might call you back), for slow riverside sunsets, and for just being present.
And one more piece of advice: keep it flexible. Some of the best memories come from unexpected detours—whether a local festival, a riverside bench, or a shop you might otherwise have walked past. Callicoon rewards curiosity.