Livingston Manor eats far above its weight class. A few blocks of Main Street and the roads just outside town hold everything from four-generation biscuit recipes to a James Beard-recognized dining room. Hours shift with the seasons up here — most places post current hours on Instagram, so check before you drive over.
On and around Main Street
The Kaatskeller
Wood-fired pizza with indoor tables and a garden out back. The Margherita and the New Haven-style white pie are the moves. This is the default "first night in town" dinner, and it's five minutes from the cottage.
Main Street Farm
Half market, half café — sandwiches and soups built from local farm ingredients, plus groceries, coffee, and pantry stock for your stay. Our go-to for provisioning the cottage kitchen.
The Walk In
The town's beloved breakfast spot, famous for flaky buttermilk biscuits from a four-generation-old recipe. Get the hot honey butter biscuit and thank us later.
Threshold
Korean cooking with locally sourced produce and real vegan and vegetarian options — the kind of restaurant you're surprised and delighted to find in a town of a thousand people.
Van Smokey
Meat-forward restaurant and bar that doubles as the town's fun engine — smoked meats, burgers, cocktails, weekend karaoke, and outdoor movie nights.
Stumble Out
Seafood and elevated cocktails in a colorful room; regulars swear by the key lime pie. Sidewalk spritzes in summer.
Sunshine Colony & Upstream
Two spots for wine people: Sunshine Colony pours by the glass with wood-fired dinners in partnership with local cooks, and Upstream stocks natural wine to drink in or take back to the fire pit.
Worth the drive
The DeBruce
The special-occasion pick: a 12-room inn on 600 acres overlooking the Willowemoc valley, with a tasting-menu dining room that earned a James Beard Award semifinalist nod in 2024. Book well ahead.
Arnold House Tavern
A proper tavern atop Shandelee Mountain — jukebox, pool table, fireplace. Ten minutes of winding road from town, and worth every turn.
Breweries & spirits
Catskill Brewery
The town brewery, minutes from the cottage, with a taproom pouring six days a week and a food truck usually parked outside.
Upward Brewing Company
A brewery with its own mountain: 120 acres, a spring-fed pond, and the "Beer Mountain" trail — a short forest climb to a 1,870-foot overlook that turns a pint into an outing.
Do Good Spirits
Veteran-owned distillery in nearby Roscoe with award-winning vodka, gin, and bourbon; tastings support the Third Option Foundation.
Evelyn's Ice Cream Bar
Homemade soft serve with natural flavors — the correct way to end a summer evening on Main Street.
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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