Day 1: New York City to Livingston Manor to Cochecton (154 miles)
Leave the Manhattan skyline behind on the two-hour drive north on the Palisades Parkway. Hop on NY-17 to enter the Catksills Region, which begins in the scenic former lumber town of Barryville. (Most visitors approach via touristy Woodstock.) Merge onto NY-97 and follow the steep-banked Delaware River that separates New York from Pennsylvania, keeping an eye out for bald eagles riding the thermals. After 30 minutes, you’ll arrive in the tidy town of Narrowsburg, where creative New York City transplants have set up shop on Main Street. Narrowsburg Roasters (25 Main St.; 845/252-6688; breakfast for two $12) was opened by former West Village set designer Will Geisler in 2006. Geisler makes a killer latte, and his biscotti and maple shortbread are addictive. Next door, browse the well-edited collection of housewares—from handwoven Brazilian bedspreads to cowhide chairs, at Nest. Across the street you’ll find Enochian Inc. (55 Main St.; 845/252-3828), a modern custom dress shop, which expanded last year with a men’s line of leather jackets and alpaca sweaters.
Drive northeast for 20 minutes along woodsy NY-52 to the Golden Guernsey (31 Mitchell Pond Rd. E., Cochecton; 845/932-7994; doubles from $125). The former barn is painted bright marigold, decorated with Midcentury furniture, and run by ex-Brooklynite and graphic designer Amy Miller. For supper, follow NY-52 for 45 minutes north and turn off on Shandelee Road toward the fly-fishing town of Livingston Manor, where tackle and taxidermy shops stand alongside galleries and an organic-food market. The Lazy Beagle Pub & Grill (2 Pearl St., Livingston Manor; 845/439-3405; dinner for two $50), a gastro-tavern popular with urban weekenders, serves shepherd’s pie and Beaverkill Brook trout, while seasonal produce like Swiss chard and beets come from the chef’s garden. Back at the Golden Guernsey, finish the evening with a sampling of decadent house-made ice creams such as coffee-bacon and vanilla-rosemary.
Day 2: Cochecton to Roxbury (82 miles)
Fuel up with the inn’s hearty breakfast frittatas and omelettes made with eggs from Miller’s own free-range chickens, but don’t linger too long: an early start on NY-52 may reward you with sightings of black bears and glimpses of morning mist over the hills. Turn onto NY-55, which passes through mountainous Ulster County and by the Neversink and Rondout reservoirs, two of six protected basins that provide New York City with drinking water. Two dozen villages were deserted and then flooded between 1910 and 1928 to create them, and you can still see stone foundations and old orchards protruding from the water’s glassy surface.
At Rondout, continue 13 miles on County Road 42 to West Shokan and coast 15 minutes east on Route 28 to Shokan. Pair some Swedish pastry with coffee from micro-roaster Monkey Joe at the Scandinavian Grace Kafe (2866 Rte. 28, Shokan; 845/657-2759; snacks for two $10). The café’s adjacent showroom is filled with Danish teak desks, Hans Wegner Wishbone chairs, and Swedish-designed (but locally made) cabinetry. Double back on Route 28 and take a tour of Kate’s Lazy Meadow (doubles from $195), a kitschy motel owned by B-52’s singer Kate Pierson. On the grounds, you’ll find 10 wood cabin suites and seven Airstream trailers with psychedelic-colored walls, vintage cabinets, and, outside, hammocks. The Hanover Farm Stand (5200 Rte. 28; 845/688-5667) across the street sells blueberry pie and wedges of local Tonjes Farm cheese around the clock. Save room in your lunch sack for a visit to Grandmère Yvonne’s Kitchen (6285 Rte. 28, Phoenicia; 845/688-7340), six miles north on Route 28. Run by 82-year-old Yvonne Taule, a French former model, the charming roadside cabin stocks crusty potpies and wild-boar pâtés. Pretty picnicking sites abound, the best of which is Ashley Falls, 20 minutes north on Route 214. Take your provisions up the easy, quarter-mile hiking trail, spread a blanket, and tune in to the sound of cascading water.
Next, zigzag up Route 23A for 45 minutes and check in to the whimsical Roxbury Motel (doubles from $99). The converted motor lodge added two spas and nine rooms with interiors inspired by 1960’s TV classics like I Dream of Jeannie and Bewitched. If the bold color scheme overwhelms, roll down Route 28 to restore your sense of rusticity at the Peekamoose Restaurant & Tap Room (dinner for two $60), a refurbished farmhouse helmed by chef Devin Mills, who’s worked in the kitchens of Manhattan’s Gramercy Tavern and Le Bernardin. Wood-grilled steaks and 35 beers on tap draw a lively crowd.
Day 3: Roxbury to Walton (52 miles)
Rise and shine in bucolic Delaware County, which was settled in the 19th century by Scottish dairy farmers; Guernsey and Jersey cows still dot the hilly landscape. Cassie’s Café (Main St., Roxbury; 607/326-7020; breakfast for two $12) is just around the corner from the Roxbury Motel and serves one of the best breakfasts in town. After getting your fill of strawberry-topped Belgian waffles or orange-cranberry muffins, head 25 minutes south on Route 30. If it’s Saturday, look for the old round barn that houses the Pakatakan Farmers’ Market (Rte. 30, Halcottsville; 845/586-3326) and stock up on cider-washed raw cheeses and fruit spreads such as strawberry rhubarb. Continue south along Route 28, which opens onto hemlock-capped hills dotted by crumbling red barns, and stretch your legs in the village of Andes. Nini Ordoubadi’s modern shop and tea bar, Tay Home (131 Main St., Andes; 845/676-4997; tea for two $6), sells her hand-blended, fragrant oolong, green, black, and herbal teas. Grab a tin of her best-selling Better Than Sex blend—a rich mix of rooibos tea, Belgian dark chocolate, and peppermint. Next, stroll over to Kabinett & Kammer (7 Main St., Andes; 845/676-4242). The curiosity shop is skillfully crammed with quack-medicine collectibles, vintage school maps, and antique natural-history prints. To add a dose of country chic to your wardrobe, look no further than Clementine Vintage Clothing (72 Main St., Andes; 845/676-3888). The secondhand clothing store run by onetime Ralph Lauren exec Misha Mayers stocks everything from trenchcoats to checked hunting shirts.
Onward to Delhi (pronounced DELL-high), 13 miles north, then switch to Route 10 toward Hamden, where the road heads west away from the thickly forested mountains into rolling farmland. Stop in Hamden for a jar of thick Firefly Farms maple syrup and a hunk of sun-dried-tomato-studded meatloaf at the Lucky Dog Farmstore & Café (35796 Rte. 10, Hamden; 607/746-8383; lunch for two $15). Then settle into one of the four spacious, safari-style farm tents at Stony Creek Farmstead (1738 Freer Hollow Rd., Walton; 716/226-6323; tents from $219), equipped with purring wood stoves and kitchens you can fill with bone-in beef rib steaks from the farm’s honesty shop. If you’re so inclined, resident farmers Kate and Dan Marsiglio will put you to work picking vegetables, gathering eggs from heirloom chickens, or milking Sierra, the family’s doting brown-eyed Jersey—with all that activity and fresh air, you’re guaranteed a restful night’s sleep.
Adam H. Graham is a writer based in Brooklyn, New York.