Some trips you plan down to the last mile. Others… well, they sort of happen to you. The Catskills have a way of turning a quick afternoon drive into an all-day wandering, especially when you let the curves of Sullivan County’s roads make the decisions. It’s the kind of place where the scenery convinces you to keep going “just to see what’s around the next bend,” and where veering off course might mean meeting your new favorite ice cream cone in Callicoon.
This is your unofficial, totally non-linear guide to driving Sullivan County’s backroads. There will be rolling hills. There will be farm stands. There will be side roads you’ll swear weren’t on the map five minutes ago. And yes there will be ice cream.
The Art of Getting Lost on Purpose
The first thing to understand about a scenic drive here is that “scenic” isn’t a marketing word, it’s just how the place is built. Sullivan County is stitched together with two-lane roads that meander past old dairy barns, stretch along trout-filled creeks and rise into overlooks that spill views clear to the horizon.
You could follow Route 97’s Upper Delaware Scenic Byway along the Delaware River, but the magic often lives on the little roads that branch away from it. Think of them as tributaries, each one leading to its own small-town square, wildflower field or hand-painted “fresh eggs” sign nailed to a fence post.
Tip from locals: don’t worry about cell service. You’ll lose it in places and that’s fine. That’s how you find the old iron bridge you’ll want to photograph or the trailhead with a parking lot the size of a living room.
Route 52: From Liberty to Youngsville
Start your wander in Liberty, a town that wears its Catskills history with pride. Grab a coffee at New Munson Diner, yes, the chrome beauty once sat in Manhattan before making a new life here, and don’t leave without trying their corned beef hash and eggs, a hearty classic that hits like sunrise in comfort form. The salty, tender hash paired with perfectly cooked eggs is exactly what you need before the roads start rolling out in front of you. Head west on Route 52 and watch as storefronts give way to rolling farmland.
The road undulates through green valleys and pastures. In the summer, you’ll pass fields dotted with round hay bales that look like they’ve been casually tossed there by giants. Come fall, these hillsides are a quilt of red maples, gold birches and bronze oaks. Every few miles, you’ll spot a roadside farm stand, often on the honor system. A jar for cash, a handwritten sign and maybe a curious barn cat watching you pick your tomatoes.
Before Youngsville, look for side roads toward Jeffersonville. They’ll take you through narrow wooded stretches where sunlight flickers through the leaves, creating that strobe-like effect that makes you feel like you’re driving through a memory.
Ice Cream Break #1: Jeffersonville’s Creamy Core
Jeffersonville isn’t big, but it has a knack for drawing you in. The Jeffersonville Bake Shop is great for coffee and pastries, but when the weather’s warm, the real pull is Myers Century Farm.
A family-run dairy since 1837 that’s as rooted in the land as the maples you drove under, Myers Century Farm is the real deal. Their self-service farmstand, open 24/7! offers Ri’s Farm Made Dairy ice cream that’s creamy, wholesome and hormone-free, with flavors that change like the seasons. Mint ice cream sandwiches rolled in sprinkles, lavender-honey scoops, or straight-up vanilla that tastes like nostalgia on a cone, take your pick, pay at the honor box and wander back to the road licking.
Down to Callicoon: Where the River Meets the Road
From Jeffersonville, a gentle 15-minute drive west drops you into Callicoon, a Delaware River hamlet with cobblestone charm and a Saturday farmers’ market that’s half social event, half gourmet wonderland.
But here’s where the unplanned part of the day kicks in: tucked just off Main Street is Ollie Grey’s, home to what some swear is the best soft-serve in Sullivan County. Maybe it’s the creamy texture, maybe it’s the way the cone feels just right in your hand as you walk toward the river. Either way, this is where a “let’s just drive for a bit” afternoon turns into sitting by the water, shoes off, watching the sunlight scatter across the Delaware.
Route 97’s Secret Sidekicks
While Route 97 gets the glory for its sweeping river views, especially the Hawk’s Nest section near the Orange County line, its side roads are where you find the stories. Head south out of Callicoon and turn onto any number of backroads toward North Branch, Fremont Center or Hankins.
Expect to share the road with deer, cyclists and the occasional tractor. You’ll pass clapboard farmhouses with laundry snapping on the line, and roadside shrines of wildflowers growing in rusted milk cans. In summer, the air smells faintly of cut hay; in winter, it’s sharp and piney.
Ice Cream Break #2: Roscoe’s Fishing Fuel
Keep winding your way southeast until you hit Roscoe, “Trout Town, USA,” where the Beaverkill and Willowemoc meet in a glittering confluence. This stretch of road feels like it was designed by a fly-fisher’s daydream, dappled light through hemlocks, the sound of moving water never far from your open window and a pace that encourages you to take curves a little slower just so you can look around. Roscoe’s main street has the easy, lived-in feel of a place where everyone knows who caught the biggest fish this week.
When you reach town, veer into Nif-T’s Ice Cream, tucked right next to the Roscoe Diner. It’s the kind of place that feels proudly small-scale, soft and hard scoops, honest service, and indoor counter seating that can shift you from dusty traveler to neighbor in one lick. Their sundaes are piled high, the kind of generous that makes you want to sit awhile, maybe wander outside to a picnic table and catch the sun glinting on river water.
Livingston Manor: A Creative Pause
From Roscoe, Route 17 will get you to Livingston Manor in a flash, but the back way, Route 206 to Old Route 17, is better for the soul. This is where Sullivan County’s creative undercurrent bubbles up: small galleries, fly-fishing shops that double as community hubs, and Willow & Brown, a home goods store that makes you want to redecorate your entire house in reclaimed wood and enamelware.
Step inside Catskill Art Space, where whitewashed walls cradle bold canvases, and sunlight slants through tall windows like a spotlight for inspiration. Down the street, a former schoolhouse hums with quiet industry, potters at their wheels, jewelers at their benches, and painters capturing the shifting light of the mountains. Here, art isn’t an event you attend, it’s the air you breathe.
The Road Less Obvious: Swan Lake to Hurleyville
For a quieter stretch, point your car toward Swan Lake. The road skims along the water’s edge, where loons call in the early morning and mist rises like a curtain. From there, drift into Hurleyville, a hamlet that’s quietly reinvented itself as a hub for arts, food and inclusive community events.
Pause for lunch at Forage & Gather, where seasonal sandwiches build themselves from local meats, cheeses, hummus, and microgreens, tucked between freshly baked sourdough or a soft brioche bun, just ask to “build your own,” and they’ll piece it together with warm care. The café hums with small-town rhythm, sunlight on wooden shelves lined with specialty groceries and handmade local gifts.
Ice Cream Break #3: Rock Hill’s Classic Cone
On the way back toward Liberty, make a sweet detour to J’s Soft Serve in Monticello, a true roadside gem where the cones are as tall as the smiles behind the counter. The soft-serve here is impossibly creamy, whether you go classic vanilla, chocolate, or twist, and the sundaes come layered with hot fudge, whipped cream, and the perfect cherry on top.
There’s plenty of outdoor seating, so you can linger under the late-afternoon Catskills sky, letting the last miles of your drive unfold with a cone in hand and no rush to get anywhere.
When the Road Gives You More Than a Destination
Here’s the thing about driving Sullivan County’s backroads: they’re not just about where they lead, but how they make you feel on the way there. A slow climb up a shaded hill, windows down, the smell of rain on warm pavement, these are the little souvenirs you take home without realizing it.
You might start with a loose plan, say, “We’ll drive to Callicoon, maybe hit the market, get ice cream” but somewhere between the creak of an old covered bridge and the sight of a hawk circling over a hayfield, you’ll stop caring about the plan. That’s the point. The roads here are more about rhythm than route.
A Few Practical Tips for Your Wander
- Bring cash. Some of the best ice cream, produce stands and pie slices are cash-only.
- Don’t rush. Locals wave you through stop signs, but no one’s in a hurry.
- Mind the seasons. Summer is lush, fall is fiery, winter is hushed and beautiful, and spring smells like the world is brand new.
- Respect private property. That gorgeous red barn might make the perfect photo but remember, it’s someone’s home.
- Talk to people. Ask the person behind the counter where they get their ice cream. You might end up in a place not on any list.
The Road That’s Never the Same Twice
Out here, there’s no single “right” way to take a drive. Every turn holds the potential for something unexpected, a farm stand you’ve never noticed, a sunlit field that stops you in your tracks, or an ice cream cone that somehow tastes better because you didn’t plan on finding it.
In the Catskills, especially in Sullivan County, the best drives aren’t about plotting the route. They’re about following the mood of the day, letting the road surprise you with its own rhythm. One moment you’re coasting under a canopy of maples, the next you’re leaning on a picnic table, working through a vanilla-chocolate twist with extra sprinkles.
Come for the backroads. Stay for the stories you didn’t mean to find.
