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Four unforgettable day trips from New York City

Make this the summer you fall in love with New York’s Hudson Valley.

New York’s rather grand Hudson Valley region is many different things to many different people—this is not surprising. The land of Washington Irving’s Rip Van Winkle, for centuries now a haven for artists and artisans, after all, occupies a rather sizable chunk of real estate, stretching 150 miles north of New York City to the remote state capital of Albany. To truly get a handle on the region takes more time than most people have at their disposal.

In some places it is a diamond in the rough; in others—where man hasn’t gotten to it, mostly—it is drop-dead gorgeous. In the long run, nearly all of it is worth a visit.

Understanding that not everyone has a ton of time to wander around looking for the good stuff, here are just a few essential Hudson Valley days that highlight very different (and rather special) corners of one of the country’s most unique and intriguing places. This is not an inclusive list, by any means. It is a list of very good things, all time-tested, in some cases, over and over again. Do enjoy.

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#1 AS GOOD AS IT GETS Located not far from the increasingly fancified (and very historic) town of Rhinebeck, Bard College is not only one of the nerdiest little liberal arts institutions in existence, it is also a showcase of appealing architecture spanning more than 100 years, clustered along the northern end of one of the Hudson Valley’s most scenic back roads. During summer, the best reason to drop by is the school’s SummerScape event (through August 20), a free-wheeling festival of culture and art that’s far from boring. In season, book tickets to a concert at the Frank Gehry-designed Fisher Performing Arts Center, a mini-version of LA’s Disney Hall in the middle of a quiet field. Expect performances by the American Ballet Theater and American Symphony Orchestra; college president Leon Botstein conducts the Orchestra. Before or after a show, hike the 1.5 miles of trail at Poet’s Walk Park, just down River Road from the college campus. These pastoral estate lands are maintained by Scenic Hudson, a major force for preservation and park building in the valley; trails lead you through fields, forest and ultimately down to the Hudson River for excellent views of the Catskill Mountains. Hungry? Even if you’re not, make a stop at the Montgomery Place Orchards farm stand, over on Route 9G. This isn’t just another farm stand; these orchards, on and around the grounds of River Road’s historic Montgomery Place mansion, are part of the revival of many antique apple varietals that had been all but lost to the history books. The stand is one of the best in the valley for its carefully curated mix of local products and its faithfulness to selling only the very best of what’s just been harvested, from blackberries in mid-summer to root vegetables just before everything shuts down for the year. If it’s for sale when you’re there, grab a mason jar of the house hard cider, produced just around the corner. For dinner, head around the corner to Tivoli, a sleepy village where Bard students and old-school locals and big names like Jann Wenner and Natalie Merchant mix and mingle. For such a small town, there’s more than one or two fine options, but for best results, at least start your evening at the bar at Panzur—they do a great cocktail.

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#2 WINE + CHEESE + THE TACONIC Could the Hudson Valley ever end up giving Northern California a run for its money in the wine and food production department? Probably not. But what the valley might lack in weather and output, it definitely makes up for in atmosphere. We’re truly not far off from parts of the region morphing into the likes of California’s Sonoma County—cute in some places, refreshingly workaday in others, but always pleasant and scenic and full of people who are escaping big cities nearby both as residents and visitors. Not that there’s no good wine or cheese—in fact, there’s plenty. For best results, stay east of the river—start at Millbrook Winery, where the West Coast-worthy grounds and onsite café are half the fun. Next, head over to Sprout Creek Farm, out on the east side of Poughkeepsie. This not-for-profit organization with years of experience specializes in raw cheeses of all ages and types; their aged, nutty Ouray is becoming a staple at parties and getting some nice national attention, too (their little on-property shop is open Tuesday through Sunday from 10-5, during the summer). Next, head up the Taconic Parkway to Columbia County, where it’s all about the Hudson-Chatham Winery, which even the biggest snobs will admit shows real promise. Nearby, pop by the mothership of the Old Chatham Sheepherding Company; visitors are welcome to come say thanks to the sheep for those amazing cheeses that are available in nearly every good grocery store in New York City these days. A self-serve stand on property is a good place to stock up.


#3 BEYOND THE GATES The town of Hyde Park, as a realtor would say, does not show well. Back in the old days, when Franklin Delano and Eleanor used to live here, down the street from the Vanderbilt clan, back when the Culinary Institute of America first set up shop on its very nice spot up above the river—things were nicer then. Back then, people had class. Then came along a bunch of shortsighted developers, who decided to suburbanize the joint, turning a quiet river village with a serious pedigree into a fairly hideous exurb. Don’t, however, let the aesthetic terrorists win: Hyde Park’s ugly is assuredly only skin-deep—get behind the town’s many gates and you’ll see. The impressive Roosevelt lands are where you start—this isn’t just another old house tour; there are more than 10 miles of beautiful trail that link the main riverfront property up to Eleanor’s Val-Kill. It’s all under the supervision of the National Park Service, meaning it always looks absolutely gorgeous. There’s a pleasing diversity of terrain, too—a riverfront cove, marshlands, hills, fields, creeks, deep forest—you could get lost in here for more than a day. For an impressive bit of contrast, next make a stop at the Vanderbilt Mansion National Historic Site. Where the Roosevelt trails are all about wandering and enjoying nature, everything here seems relatively manicured. Still, the river views from the bluff-top mansion (and further down the bluff, on the north side of the property) are epic. Skip the house tour, unless you want to be reminded of the fact that money can’t buy people taste. If you are lucky enough to be up here on a weekday—and you really should make that happen—make like a future celeb chef and dine at the Apple Pie Café, the most casual restaurant on the pristine Culinary Institute of America property, also located along the river, The buzz is fantastic and the food is one of the best lunches in the valley. Unlike at the other restaurants on property, nobody will notice or care if you look like you just wandered in from a day of hiking (Note: The cafe is closed for the first few weeks of August).

#4 THE SLEEPER AWAKES Unlike other Hudson Valley cities, Kingston hasn’t had a convenient rail connection to New York City in eons. Whatever that has meant for the regional economy over the years, one thing’s for certain—if it had been easier to get here over the years, Kingston would probably not look like it does today, which is to say, much like it has looked for a very long time. This modestly sized and very old Valley town has been passed by in many ways, but that’s the funny thing about being out of fashion for such a long time—suddenly, you’re ahead of the curve again. These days, its relentlessly retro appeal seems to be working for it, for a change—in neighborhoods upmarket and not, absolutely stunning stone and Victorian homes line blocks that are starting to catch on with a more cosmopolitan crowd. Your first—and if you’re pressed for time, only—stop should be the Stockade District, which has roots going back to the 1660s. Here, the handsome Old Dutch Church, built from the local bluestone, makes a nice backdrop for the city’s pleasant Saturday farmers market; nosh your way through and chat up the locals. What next? You’re in Kingston, a town that’s never far from nature—hardly surprising, when you consider the city limits on the western side border the vast wilds of Catskill Park. Today though, focus on the Hudson Valley end of things; head out the back side of town, over the Rondout River and down Union Center Road, which winds its way through the Marlboro Mountains, a low-profile but very scenic area containing the gorgeous Shaupeneak Ridge Preserve. Here, approximately 800 feet above the Hudson River, 6 miles of trails on 700 acres offer everything from big valley views to a pleasant loop around Louisa Pond. Just a few minutes’ drive and you’re back in town; here, the Stockade Tavern—located across from the old Senate House, briefly the seat of state government during a little kerfuffle we now know as the Revolutionary War—is a particularly good cocktail bar; its existence and success is a testament to just how quickly the area is changing, as moribund neighborhoods and nearby villages soak up an increasing number of city refugees who like nature and quiet but also appear to enjoy heading out once in awhile for smart beverages in an almost chic setting. Speaking of things you would not expect to find in a town of this size, around the corner on North Front Street you will find Boitson’s, an urbane little hangout that would fit nicely into New York’s West Village, except it’s here. Expect oysters, fried chicken, good vegetarian options, conviviality, coziness. You should make a reservation on weekends.

Booking a trip? If you’re looking for cheap airfares to New York, start your search at CheapFlights, or compare multiple sites at once with BookingBuddy. Don’t forget that bundling your flight and hotel together can save you a lot of money; give it a try at either Orbitz or Expedia—both are great places to start a simple airfare search, too. If you’re just after the best Hudson Valley hotel deals, start your search at Hotels.com or Priceline, where you can save up to 60 percent on any given night by taking advantage of their Express Deals feature. (This simple tool has probably saved us—no joke—thousands of dollars over the years.) Don’t forget, you can also cross-reference a ton of hotel user reviews with the best rates available from more than 200 web sites at TripAdvisor. If you need a rental car, begin your search by swinging wide to get a sense of the market—a site like Booking Buddy lets you check pretty much every site worth knowing in just a couple of clicks.

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