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.