1. Where to Stay
Look out over the Hudson at the Rhinecliff Hotel (from $160), the recently renovated boutique hotel where rooms come with balconies, wide-board flooring, and giant whirlpool baths.
Be one of few guests at the Madalin Hotel (from $199), where Eastlake-style antiques are paired with flat-screen TVs in the eleven-room inn decorated by the team behind the Chelsea Hotel’s renovation. Have a nightcap at the gorgeously restored, nineteen-foot-long 1909 bar downstairs.
Cook for yourself in the airy, high-ceilinged guest cottage at the Sheeley House Bed and Breakfast (from $200). The stately brick main house dates back to the 1830s.
2. Where to Eat
Eat local at Another Fork in the Road (1215 Route 199; 845-758-6676), a tavern that draws heavily from local ingredients. The burger is made with beef from North Wind Farms down the road.
Dine in at Main Course, the New Paltz takeout and catering staple that moved into a large, eat-in space this fall. The picture windows in the dining room look out onto Shawangunk Ridge.
Try one of the seafood specials at Aroi, the Thai restaurant located in a restored clapboard house in the village of Rhinebeck. Iron palates can risk ordering one of the intricately spiced panang curries “Thai hot.”
3. What to Do
See the beginning of Tuthilltown Spirits’ Hudson Baby Bourbon — from the grinding to bottling operations — before it ends up behind the bar at places like the Brandy Library and Char No. 4. Tour the distillery, and sample the unaged corn whiskey, a throwback to “white lightning” of yore ($15). Stock your liquor cabinet with bottles of the Heart of the Hudson Vodka and New York State whiskey.
Take a free tour of Harvest Spirits, third-generation apple-farmer Derek Grout’s award-winning distillery. Try the aptly named Core Vodka, found on the drink menu at the Farm on Adderley, or the newly released, quad-distilled Cornelius Murray Apple Jack, aged one year. Sober up with a bag of apples and some cider doughnuts from the farm stand on your way out.
Sign up for one of master distiller Jason Grizzanti’s three-and-a-half-hour winter-weekend classes ($50–$75) at the Warwick Valley Winery and Distillery. Beginners load fermented mash into a 210-liter copper still during a fruit-brandy series, while more advanced classes focus on whiskey-making and include a technical talk by Grizzanti. Enjoy the complimentary lunch of homemade pizzas and sandwiches in Warwick’s converted barn café.
4. Insider’s Tip
On Saturday nights, former Band drummer Levon Helm opens his home-recording studio for hours-long, freewheeling concerts he calls Midnight Ramble Sessions ($150; $125 for parties of five or more). Previous weekly guests include like-minded music legends like Emmylou Harris, Ramblin’ Jack Elliott, and Garth Hudson. Book online a couple of weeks in advance.
5. Oddball Day
Bundle up to enjoy “Waterfalls” artist, Olafur Eliasson’s “The Parliament of Reality” at Bard College. The outdoor exhibit was installed last spring, but the 24-tree-ringed pond and stone bridge take on a special, stark beauty in winter. Take a short drive east on Route 199 to visit the “other” Red Hook and its indoor, monthly Winter Farmers Market at the Elmendorph Inn (7562 Route 9, Red Hook; 845-399-4582). Inside the former stagecoach stop, snack on scones and pain au chocolate from Gigi’s Market as you examine winter vegetables and fresh-baked breads and pies. In the afternoon, head south on Route 9 to Poughkeepsie’s Walkway Over the Hudson, a 120-year-old former railroad freight bridge that opened for pedestrians in October 2009. The longest elevated walkway in the world, it provides stunning views of the Hudson River and Valley. Robust souls can also hike a three-and-a-half-mile trail that crosses the more diminutive Mid-Hudson Bridge. Sate your stoked appetite at Soul Dog Neighborhood Eatery & Bakery, a high-end hot-dog joint just five minutes from the Walkway that tops Applegate Farm wieners with creative fixings like caramelized onions and Thai peanut sauce. At night, watch a live broadcast from the Met or see a classic like 2001: A Space Odyessy in Poughkeepsie’s Bardavon 1869 Opera House, a restored neoclassical gem complete with working Wurlitzer organ and a hand-painted dome ceiling. Have a post-show bite at the Artist’s Palate, a bistro and wine bar decorated with the works of local artists.
For a directory of craft distilleries across the country, as well as information on courses and liquor-related reading, visit the website of the American Distilling Institute.
Dutchess County Tourism offers information on local history and attractions.
Ulster County Alive covers the county on the Western side of the Hudson River.
Historic Hudson Valley operates a network of historic sites.