The Ultimate Sullivan County Bucket List
Sullivan County isn’t just a place you visit — it’s a place you experience. From lazy river floats and misty waterfalls to antique-filled main streets and candlelit dinners, this corner of the Catskills invites you to slow down, explore deeply, and savor the magic of small moments.
Whether you’re planning a weekend escape or a longer stay, here’s the ultimate Sullivan County bucket list to inspire your next getaway.
🌊 Float Down the Delaware River
Few experiences feel more quintessentially Sullivan County than floating down the Delaware River on a warm summer day. Rent a tube, kayak, or canoe, let the current guide you, and soak in the peaceful scenery. It’s equal parts adventure and relaxation — and a must-do for first-time visitors.
🏘 Explore the Charming Small Towns
Each town in Sullivan County has its own personality and hidden gems. Spend a day wandering:
Livingston Manor for shops, cafes, and fly-fishing culture
Narrowsburg for river views, boutiques, and art galleries
Callicoon for a classic main street and laid-back vibes
Roscoe, Trout Town USA, for outdoor culture and cozy eateries
Take your time — the magic is in wandering.
🕰 Spend a Day Antiquing
Antique lovers, rejoice. Sullivan County is full of vintage shops, barn sales, and hidden treasures waiting to be found. Make a day of it by hopping between stores, chatting with shop owners, and uncovering one-of-a-kind pieces with history and character.
🥕 Visit Local Farmers Markets
There’s nothing like strolling a farmers market with a coffee in hand. From fresh produce and baked goods to local honey, flowers, and handmade crafts, these markets are a beautiful way to support local farmers and makers — and experience the region like a local.
🍎 Go Apple Picking in the Fall
When autumn arrives, apple picking becomes a bucket-list essential. Crisp air, rolling hills, and rows of apple trees make for the perfect fall day. Many orchards also offer cider, donuts, and seasonal treats — making it a full sensory experience.
🍺 Sip Your Way Through Cideries & Breweries
Sullivan County is home to a growing craft beverage scene. Spend an afternoon visiting local cideries and breweries, sampling small-batch flavors, and enjoying scenic outdoor seating. It’s the perfect mix of indulgence and Catskills charm.
🥾 Hit the Hiking Trails
From gentle nature walks to rewarding summit views, there’s a trail for every level. Explore forest paths, mountain overlooks, and quiet preserves that showcase the natural beauty of the region. Don’t forget your camera — the views are worth it.
💦 Chase Waterfalls
Waterfall hunting is a year-round adventure here. After a rain or during spring thaw, the falls are especially dramatic. A short hike often leads to breathtaking scenery, making it one of the most rewarding ways to explore Sullivan County’s wild side.
🎶 See a Show at Bethel Woods
No Sullivan County bucket list is complete without a visit to Bethel Woods Center for the Arts. Whether you’re attending a concert, exploring the museum, or simply soaking in the historic grounds of the original 1969 Woodstock festival, it’s an unforgettable experience.
🍽 Treat Yourself to a Fancy Dinner
After a day of adventuring, dress up just a little and enjoy a refined dining experience. Sullivan County offers incredible farm-to-table restaurants and intimate dining spots where the food is thoughtful, seasonal, and meant to be savored.
🔥 Bonus Bucket List Moments
If you have extra time, don’t miss:
Stargazing by a fire pit
A cozy cabin night with wine and board games
Winter snowshoeing or cross-country skiing
A quiet morning coffee overlooking the mountains
A scenic drive through back roads and river valleys
✨ Stay Somewhere That Feels Like Part of the Experience
Where you stay matters just as much as what you do. At Casskell Stays, our curated homes place you right in the heart of Sullivan County’s best experiences — whether you’re seeking adventure, relaxation, or a little of both.
Start checking off your Sullivan County bucket list one unforgettable stay at a time.
