Livingston Manor is a one-Main-Street town that somehow fits a James Beard-recognized restaurant, a world-class art space, two breweries, and the most storied trout water in America into a few square miles of forest. It's two hours from the George Washington Bridge and feels a century further away. Here's how we'd spend a weekend.
Start on the water
The Willowemoc runs right past the village, and the Beaverkill is just over the hill — together they're the birthplace of American dry-fly fishing. Stop into Dette Flies on Main Street, the oldest family-run fly shop in the world, for gear, flies, and guided trips, and visit the Catskill Fly Fishing Center & Museum to understand why anglers make pilgrimages here. Even if you never pick up a rod, the rivers are where this town's soul lives.
Read the full fly-fishing guide →
Eat and drink well
For a town this size, the food is absurd. Wood-fired pizza at The Kaatskeller, four-generation biscuits at The Walk In, Korean cooking at Threshold, sandwiches from Main Street Farm, and — for a big night — The DeBruce, a 2024 James Beard Award semifinalist overlooking the Willowemoc valley. Two breweries flank the town: Catskill Brewery and Upward Brewing, whose 120-acre property comes with its own hiking trail.
See the full eat & drink guide →
Get into the woods
The O&W Rail Trail runs along the valley (it literally borders our backyard), Covered Bridge Park shelters a 19th-century covered bridge over the Willowemoc, and the Willowemoc Wild Forest holds 40+ miles of marked trails. Within a half hour you can climb the Balsam Lake Mountain or Red Hill fire towers for 360° views over the Catskills.
Around town
Catskill Art Space anchors Main Street with 4,500 square feet of galleries — including works by Sol LeWitt and James Turrell — and admission is free. Browse One Grand Books (every title picked by a notable person as a "desert island" book), outdoor goods at Old Souls, design-minded homewares at Homestedt, Corners, and Nest, then get a soft-serve at Evelyn's Ice Cream Bar. Ten minutes down the road, Roscoe — "Trout Town USA" — adds vintage shops, an indie bookstore, and Do Good Spirits distillery.
Time it right
The Trout Parade takes over Main Street every June — the 20th annual edition lands Saturday, June 13, 2026, themed "Cirque du Trout," with floats, live music, and a vendor fair benefiting local food pantries. Summer Sundays bring the Roscoe Farmers Market (May–October). Fall foliage peaks in early-to-mid October; winter means wood stoves, sledding, and having the trails to yourself.
Black Bear Cottage is a renovated 1902 home on three wooded acres, two miles from Main Street — hot tub, fire pit, chef's kitchen, sleeps 8. Rated 5.0 on Airbnb.
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