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We love Beacon, Woodstock and Hudson, but with everyone we know heading there on the weekends, sometimes they can feel a little like Brooklyn 2.0. And since our favorite upstate activity is discovering new shops, inns, hiking paths and restaurants, we’re always game to visit some of the area’s less-traveled towns. Here are nine places worth discovering—or rediscovering—this summer.

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appalachian trail pauling ny
nancykennedy/Getty Images


Nestled in the foothills of the Berkshires and located along the Appalachian Trail, Pawling was once a haven for reticent celebrities: With its large properties and quaint village, it’s no wonder they found respite here. Now a new wave of city dwellers is flocking, in part because of the easy commute (it’s less than 90 minutes on Metro-North from Grand Central) and also because of the vast array of outdoor activities available here such as horseback riding, hiking and swimming. (After a dip in Green Mountain Lake, stay for the aptly named Music by the Lake concert series.)

harlem valley trail millerton ny
Courtesy of Millerton


For tea lovers, a visit to Millerton is a must. Stop by Harney & Sons’ flagship store for a tour, tasting and of course to stock up on your favorite teas (we’re currently obsessed with the chocolate-coconut Soho blend). But even if tea isn’t, well, your cup of tea, there’s still plenty to do here, such as antiquing and cycling. Millerton is at the north end of a recently restored bike route, the Harlem Valley Trail, which is paved and shaded by trees and extends south to Wassaic—another town worth visiting.

four brothers drive in theater amenia ny
Courtesy of Four Brothers Drive-In

Wassaic (and Amenia)

Wassaic, the last stop on the Harlem Line, is a dream for people who love to explore relics from a past era. If you’re with a group, rent out the historic Salvato Mill. Be sure to scope out the ruins of 19th-century charcoal kilns and pay a visit to Hunter Bee, which sells everything from fine antiques to quirky oddities. Finally, end your night with a double feature at the Four Brothers Drive-In one of the last of its kind—in neighboring Amenia.

hasbrouck house stone ridge ny
Courtesy of Hasbrouck House

Stone Ridge

Stone Ridge, a historic hamlet in the town of Marbletown, is known for its romantic centuries-old homes, winding roads and bucolic farmland. Dutch stone houses are plentiful here; the most famous one in the area is the meticulously restored Hasbrouck House. Even if you don’t book one of its 17 rooms, be sure to stop by Butterfield for dinner. Or pick up your own locally grown foods at the Stone Ridge Orchard and Davenport Farms, and treat yourself to a home-cooked meal. Oh and best of all, there’s a new bus line from Manhattan that services the area.

rosendale trestle ny
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This onetime cement-manufacturing town is now home to a thriving community of artists and entrepreneurs. One of the best ways to take in the colorful buildings of Main Street (home to delightful vegetarian cafésartists’ studiosbookshopstheaters and kitschy vintage shops) is from above: The Rosendale Trestle, a 940-foot continuous bridge and former railroad trestle, offers breathtaking views of Rosendale Village and Rondout Creek.

union church sleepy hollow ny
Courtesy of Sleepy Hollow

Sleepy Hollow

This legendary village is a popular fall destination (thanks to spooky Halloween cemetery tours), but it’s well worth a visit during the less-trafficked summer months. History buffs will love Philipsburg Manor, the Old Dutch Church of Sleepy Hollow and the Union Church of Pocantico Hills, which features stained-glass windows by Henri Matisse. And if you want to splurge on a memorable meal, visit nearby Blue Hill at Stone Barns, a.k.a. the restaurant that pretty much pioneered the farm-to-table movement.

culinary institute of america hyde park ny
Courtesy of CIA

Hyde Park

Rhinebeck, its neighbor to the north, may be the more recognizable name, but Hyde Park is worth a visit in its own right. The Hudson Valley town has ties to the past and future: You can visit the birthplace of FDR and taste the creations from future star chefs at the Culinary Institute of America (or CIA, as most people call it). Book yourself at a night at the oh-so-cozy Journey Inn, which is right down the road from both those attractions.

the heron restaurant narrowsburg ny
Courtesy of the Heron


The journey to Narrowsburg, a picturesque town between the Catskills and Poconos, is half the fun, since it includes traveling along the scenic Hawk’s Nest, a stretch of winding road along the Delaware River. Though small in size, the Main Street is mighty in what it has to offer—such as the Heron, easily one of the best restaurants in the region.

cooperstown ny
Pgiam/Getty Images


While Cooperstown is a little outside our ideal distance-from-the-city radius, it’s very much worth the four-hour-plus trek. You’ll feel like you’ve stepped into a Norman Rockwell painting when you visit this quaint all-American town, most famous for being the home of the National Baseball Hall of Fame. Expect your bed-and-breakfasts to be decorated in florals and your meals to be hearty.

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