Let the maples guide your days. Let crisp air steady your breath. Let yourself fall into the rhythm of a place where autumn doesn’t just arrive—it reshapes everything it touches.
In Sullivan County, fall is not just a season—it’s an atmosphere. Valleys glow in layers of scarlet, amber, and gold. River curves soften under morning mist. Farmstands spill over with pumpkins, apples, and jars of honey, each one a reminder of the land’s abundance. Roads wind through hamlets where neighbors still wave from porches, and barns stand framed by hills that seem to burn brighter with every passing day.
Here, beauty isn’t staged. It’s lived. Every turn offers a view worth slowing down for, every table tells a story of soil and season. Three days here are enough to remind you not of what you’ve left behind, but of what it feels like to truly arrive.
Day One: Seminary Hill and Callicoon
Morning: Wake with the Orchards
Wake up at Seminary Hill, a cider-focused inn overlooking Callicoon and the Delaware Valley. From your window, rows of apple trees stretch into hills set ablaze with fall color. The air smells faintly of fruit and woodsmoke. Take your coffee outside and wander through the orchard—cool air, crunch of leaves, and the scent of fruit that will soon be pressed into golden cider.
Afternoon: Main Street Strolls and Scenic Drives
Head down into Callicoon, where Main Street balances tradition and fresh ideas—hardware stores beside galleries, diners next to vintage shops, shelves lined with both old family recipes and new flavors. Take your time here; the town is best discovered on foot.
Then let the road take you: Follow Route 97, part of the Upper Delaware Scenic Byway, where the river ribbons silver below steep bluffs. Pull off at overlooks where the river braids silver through the valley. Stop at a roadside farmstand for late-season apples, pumpkins, or jars of maple syrup tapped from the very hills you’re driving through.
Evening: Dinner and River Light
Return to The Tasting Room at Seminary Hill, where dinner is built from the region’s harvest and paired with ciders pressed from the very trees outside your door. Step onto the terrace as the Delaware River catches the last of the light, steady and sure. Sleep comes easily here as leaves rustle outside your window.
Day Two: Livingston Manor and Farm Country
Morning: Coffee and Creek Trails
Drive the backroads to Livingston Manor, winding past barns and rolling fields alive with color. Stop at Main Street Farm Cafe for a strong roast and a warm bite, then head toward Willowemoc Creek. The water is famous for fly fishing, but in fall it’s the leaves that steal the show—scattering like confetti across the surface. A short walk along the banks is enough to feel how the season slows time itself.
Afternoon: Farms and Craft
Spend the afternoon moving between studios and farms. Visit a roadside stand for fresh cider donuts still warm in the bag. Step into a barn studio where potters glaze with colors drawn from fall itself. Lunch at The Arnold House, where a seasonal menu highlights what farms nearby are harvesting now. Plates change with the weather here: roasted root vegetables, trout pulled from local streams, greens picked that morning.
Take a scenic fall drive to Mongaup Falls Reservoir. The short loop trail leads to wide views—valleys burning with gold and rust—and the steady rush of water, like applause for the season. Bring a thermos of cider and linger—you’ll want the moment to last.
Evening: Supper and Song
Dine at Beaverkill Valley Inn, a place where trout is prepared with reverence for both fish and stream. The inn has been serving guests for generations, and the dining room feels timeless. If the evening allows, stay for live music—neighbors sharing songs, stories, and fiddles passed down. The sound is less performance than presence, and it carries long into the valley night.
Day Three: Bethel Woods and Backroads
Morning: Walking History at Bethel Woods
Spend your final day at Bethel Woods Center for the Arts. Stand in the field where Woodstock once shifted the world, then explore a museum that tells the story not as nostalgia, but as living history—proof that creativity can change the way people see one another.
Afternoon: Farms, Forests and Farewell
Take the long way back, letting the roads decide the pace. Pass through Monticello and stop at family-run farms and stands: wheels of cheese wrapped in wax paper, jars of honey catching the sunlight, pumpkins stacked like orange towers.
Circle past Mongaup Pond, where trails weave through birch and oak. The water reflects the sky, the woods glow in shades of gold and rust, and the stillness here feels like a gift. It’s the kind of quiet you carry with you long after you’ve gone.
Evening: A Last Taste of Sullivan
End your journey with dinner at The DeBruce. The tasting menu is a story told in courses—wild mushrooms foraged from nearby woods, greens grown in valley fields, fish from the streams that shaped the land. Raise a glass—maybe Bashakill wine, maybe one last cider from Seminary Hill—to three days that felt like more than a visit.
Carrying Autumn Home
Take with you maple syrup tapped from trees you walked under, pottery that still holds the warmth of local clay, and photos that only hint at the glow of Sullivan light. This isn’t a county that performs. It simply is—rooted, real, radiant. You’ll leave slower than you arrived, carrying autumn with you long after the last leaf falls.
