36 Hours in the Hudson Valley, New York

Suzanne DeChillo/The New York Times

Clockwise from top left: a toast at the Tuthilltown Distillery, a restaurant table in Cold Spring, relaxing by the Hudson River and a visitor on the grounds of the Olana State Historic Site. More Photos »

By FREDA MOON

Published: July 26, 2013

The Hudson Valley is vast and varied. With hundreds of miles of sandstone and granite cliffs, cattail-lined riverbanks, former factory towns, orchards, farmland and forests, the scale of its geography and the scope of its history are daunting. To spend a weekend dropping into its musty bookstores and sizable art institutions or idling between hilltop castles, divey small-town bars and doily B&Bs is like skipping a stone into a river: you bounce along, but barely break the surface. From New York City, it’s a one-hour train trip to Peekskill, at the doorstep of the mid-Hudson Valley, but the region can be fully explored only on the kind of road trip that skirts one side of the river and winds down the other, hopscotching between historic estates and detouring for farm stands, roadside diners and seductive swimming holes.

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FRIDAY

4 p.m.
1. Peek Into Peekskill

Escape the city early and arrive in Peekskill in time for “hoppy hour” ($5 per 20-ounce pint; $1 raw oysters) at Peekskill Brewery, in a 7,000-square-foot space two blocks from Metro North. Equally worthy, the Birdsall House takes its name from a local boardinghouse frequented by George Washington; it has an antique cash register, live music on weekends and an excellent craft beer list. While in town, drop into Bruised Apple Books, with a section devoted to the Hudson Valley’s past and present, a pulp mystery reading room and a vinyl record listening station.

7:30 p.m.
2. Merci Beaucoup

In February, the Culinary Institute of America — a prestigious cooking school housed in a former seminary — opened the Bocuse Restaurant, replacing the institute’s original teaching restaurant, Escoffier, which closed last year after 39 years. The space has been reborn with a new name (a homage to the Lyonnaise chef Paul Bocuse) and an airy, bistro-style interior by Adam Tihany, who designed such celebrated Manhattan restaurants as Daniel and Per Se. The French menu includes Paul Bocuse’s 1975 recipe for black truffle soup with a puff pastry lid ($12), roasted rack of lamb with sunchoke purée and glazed vegetables ($28) and, Tuesday to Thursday, a three-course prix fixe dinner ($39) that’s an exceptional bargain.

10 p.m.
3. Folkies and Newbies

After dinner, backtrack to Beacon, home to the folk icon Pete Seeger, who founded one of the area’s largest music events: the Clearwater Festival (clearwaterfestival.org), staged in Croton-on-Hudson each June. A newcomer to town, Dogwood, opened in December in a wedge-shaped brick building near Fishkill Creek, serving adventurous cocktails like the Dutch’s Moonshine- and Luxardo Maraschino-based “Moondog” ($12). The combination cocktail bar, restaurant and music venue has fast become a local hangout to rival the house-made pirogies and charms of the vintage Main Street pub Max’s on Main. Alternatively, eat early and devote the night to music. Though the Band’s former drummer, Levon Helm, died over a year ago, the Midnight Rambles he held at his Woodstock studio endure as once- or twice-monthly hootenannies, which start at 8 p.m.

SATURDAY

9 a.m.
4. Cold Spring Comfort

For breakfast, dip south to Cold Spring and the pale-yellow-walled dining room at Hudson Hil’s Cafe & Market, where there are comforting mounds of biscuits with sausage gravy ($10.25), raspberry cornmeal pancakes with orange zest (from $6.75) and specials like chocolate babka French toast ($10.95). Then, walk down to Hudson Valley Outfitters for advice on local hikes, like the not-for-novices Breakneck Ridge Trail (nynjtc.org/hike/breakneck-ridge-trail), and guided kayak trips (weather depending; from $110), including a three-mile paddle to Pollepel Island to tour the surreal ruins of Bannerman Castle ($130 including lunch).

12 p.m.
5. To the Border and Beyond

Route 9 seems an unlikely location for Texas-style dry-rubbed, hickory-smoked brisket (marbled or lean), sausage (spicy or mild) and ribs so tender the meat barely clings to the bone, but Roundup Texas Barbeque is the real deal. It is housed in a trailer parked alongside a former gas station, and serves smoked meats, Lone Star beer ($4) and classic sides like Frito pie, and jalapeño mac ‘n’ cheese. Combo plates (two meats, two sides) start at $16.50. For another relative rarity in the area, take the Newburgh-Beacon Bridge across the river to Uriel Tacos, which sells a half dozen or so kinds of tacos, including chorizo and oreja (ear), and specials like slow-cooked goat barbacoa and shrimp caldo (soup) on weekends.

2 p.m.
6. Tasting Trails

Housed in a former grist mill, the Tuthilltown Distillery became New York State’s first post-Prohibition whiskey distillery in 2007, selling its four-grain bourbon, Manhattan rye and single-malt whiskey under the Hudson Whiskey label. On weekends, tours are offered at noon, 2 and 4 p.m. ($15, including a three-spirit tasting). If wine’s your thing, the Shawangunk Wine Trail (shawangunkwinetrail.com) highlights 14 wineries, including Benmarl Winery, which claims to be the oldest vineyard in the country. The Hudson Valley Cider Alliance (cideralliance.com) is yet another beverage-centric option.

4 p.m.
7. Walking on Water

In 2009, after years of abandonment, the fire-damaged Poughkeepsie-Highland Railroad Bridge was restored and reopened as the Walkway Over the Hudson, a State Historic Park and one of the longest elevated pedestrian bridges in the world. Walk its 1.28-mile expanse in the late afternoon, when the Hudson’s celebrated light is at its most captivating. Then, take a drive through New Paltz and out on Mountain Rest Road, past the 144-year-old Mohonk Mountain House lake resort, to the Mohonk Preserve. Continue through the hamlets of High Falls and Stone Ridge, and over the Ashokan Reservoir, one of New York City’s pristine water sources. Along the way, stop in at the Last Bite for a cup of Catskill Mountain Coffee or kitschy, 1970s-era Egg’s Nest Saloon for a Sicilian egg cream ($2.75) or a slice of strawberry-rhubarb pie ($4.50).

6 p.m.
8. Old World Redux

Take two-lane back roads to Gunk Haus Restaurant, sit on the biergarten deck and look out over apple orchards and “the Gunks” — the Shawangunk Mountains, one of the country’s best-known rock- climbing ridges. Try the German breaded pork loin jaeger schnitzel, served with wild mushroom ragout and spaetzle ($19) or the addictive obatzda ($3), a Bavarian cheese dip that’s a potent mix of Camembert, Gorgonzola, beer and spices, and served with a chewy house-made pretzel.

10 p.m.
9. The Kingston Trio

When Stockade Tavern opened three years ago, selling sophisticated cocktails in a one-time Singer sewing machine factory in Kingston’s 17th-century Stockade District, the bar’s arrival foreshadowed changes for New York’s former capital. Since then, the decade-old BSP Lounge has gained enthusiastic new management and has become a sort of musician’s living room, hosting local and touring bands in a former vaudeville theater. Near the waterfront, the casual Rondout Music Lounge has a maritime aesthetic that evokes the nearby Hudson River Maritime Museum and the casual welcome of a neighborhood coffeehouse. For a more subdued evening, catch an indie movie in an old, white-steepled Methodist church building, now Upstate Films’ newest theater, in Woodstock.

SUNDAY

9 a.m.
10. Vintage Catskills

Go for a light breakfast at {outdated}, an antiques shop and cafe where mod furniture and paint-by-number paintings are sold alongside pastries and egg sandwiches. Then, drive into the hills behind Woodstock to the 900-acre Overlook Wild Forest. Look for the parking lot of the Overlook Mountain Fire Tower trail across Meads Mountain Road from the Tibetan Buddhist monastery, strung with prayer flags (there are free tours at 1 p.m. on weekends). The hike follows a wooded former carriage road to the eerie ruins of a 19th-century Catskills resort and onto the 60-foot fire tower; climb the steel structure for views that extend from the Berkshires to the Catskills.

11 a.m.
11. Hudson on the Hudson

With dozens of showrooms selling midcentury furniture with five-figure price tags, Hudson feels incongruously cosmopolitan. For brunch, sit in the backyard patio at Cafe Le Perche, a bistro and boulangerie with a bar and blazing fireplace (in season) that serves spiced brioche French toast with poached pear ($10) and a roasted four-mushroom tartine with melted Brie, baguette, micro greens and truffle oil ($11.50). Then, spend a couple of hours coveting antiques on Warren Street. The Hudson Antiques Dealers Association (hudsonantiques.net) has a guide to the 40-plus artfully curated shops. Built in 1855 as the city’s first City Hall, the restored Hudson Opera House has been transformed into a lively cultural center with a an ever-changing event calendar, a gallery that’s open noon to 5 p.m. daily and guided building tours (free).

2 p.m.
12. Far From Old School

Heading out of town, stop at the Olana State Historic Site, and the 250-acre estate of the 19th-century painter Frederic Edwin Church. The property, which is crisscrossed with trails and planted with Church’s “designed landscape,” is crowned by an elaborate Persian-style home that now holds a collection of works by Hudson Valley School painters. Back in Beacon is the sprawling, contemporary museum DIA Beacon — equal parts amusing, bewildering and bizarre. Don’t be surprised to turn a corner and meet an erotic hangman figure flashing in hot-pink neon in the distance.

LODGINGS

On 75 acres along the Hudson River, Buttermilk Falls Inn + Spa (220 North Road, Milton; buttermilkfallsinn.com) has 17 rooms and suites, a farm-to-table restaurant and spa with an indoor pool. Rooms start at $300 in high season.

Opened last year in a historic mill in Beacon, the 14 rooms (from $339 mid-week) at Roundhouse at Beacon Falls (2 East Main Street, Beacon; roundhousebeacon.com) overlook a roaring waterfall, the ultimate white noise machine. There’s also a restaurant with a wide patio above the water, a stylish bar with a fireplace and an in-house yoga studio.