How to plan the perfect Catskills weekend getaway

New Yorkers who aren’t enticed by a weekend amid the image-conscious crowds of the Hamptons often head a couple of hours north of the city for a more nature-clad respite: the Catskills. Follow their lead to discover the charms of this woodland escape. The Catskill Forest Preserve has provided the sylvan setting for cultural classics like Washington Irving’s Rip Van Winkle and James Fenimore Cooper’s Last of the Mohicans.

Fame aside, it also happens to be prime leaf-peeping territory during the fall, a hiker’s paradise in the spring and summer and an ample playground for winter sports. Here’s what to add to your weekend itinerary.

Wander through Woodstock

Though it wasn’t the actual setting for the famed music festival (that was in nearby Bethel), Woodstock has hippie roots. You can still see their traces in town, although it has become one of the more sophisticated spots in the region. Tinker Street is the main thoroughfare, home to boutiques, art galleries and plenty of cafes and restaurants.

Head to the Center for Photography for diverse works by local photographers, or to independent bookstore The Golden Notebook to pick up some vacation reading material. Yum Yum offers creative takes on Japanese noodle bowls and Southeast Asian street food, while locals’ favorite Cucina serves up Italian dishes in a restored farmhouse. And if you still have room in your stomach, Woodstock also has an outpost of Bread Alone, the Catskills-born bakery famous for its organic, wood-fired loaves and other baked treats made from locally sourced ingredients.

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Just north of Woodstock, the Overlook Mountain trail follows an old carriage road that was used in the late 1800s to transport guests to the Overlook Mountain House. The five-mile hike isn’t your average wander through the wilderness – you’ll also encounter the mountain house ruins, a historic fire tower and a Buddhist temple on your journey, not to mention some pretty stellar views of the Hudson Valley.

Find inspiration in Palenville

Proudly identifying itself as the “village of falling waters” described in Rip Van Winkle, the town of Palenville sits at the base of Kaaterskill Clove, a valley in the eastern Catskill Mountains. It was a favored location for painters from the Hudson River School, who used its unique vantage point to capture the surrounding landscape on canvas. Circle W, the town’s general store, has serviced locals since 1908 and was rescued from the wrecking ball in 2009. Since then it has evolved to cater to its discerning city-slicker visitors, offering hearty breakfast and lunch, great coffee, chai and matcha lattes, plus a curated selection of grocery goods, including local maple syrup.

Palenville is also a good base for taking advantage of the many spectacular hikes in the region. The trail to Kaaterskill Falls – one of the most popular and least strenuous – can be accessed from a verdant bend on Route 23a (the parking lot sits about 30 seconds past the trailhead if you’re coming from Palenville). Fawn’s Leap waterfall is also a well-loved swimming spot in the warmer months.

Get some color in Tannersville

Not to be outdone by Palenville, Tannersville bills itself as “the painted village in the sky,” though in this case, it’s not a literary reference. Instead it refers to the cheerful rainbow palette of the architecture on its main street where you’ll find a wide selection of do-you-really-need-this tchotchkes on offer at its quirky stores. When hunger strikes, stop by Maggie’s Krooked Cafe – a local staple for more than 30 years – or the two newer kids on the block, Mama’s Boy Burgers and Mama’s Boy Pizza. To burn off the calories afterwards, the 4.4-mile walk to Inspiration Point and Boulder Rock Trail is one of the area’s best hikes.

Earn your calories in Phoenicia

A sleepy but picturesque hamlet perched on the banks of Esopus Creek about 20 minutes from Tannersville, Phoenicia is a beloved getaway for lovers of the outdoors. Cross-country skiing and snowshoeing are the draws in winter, while fishing, tubing and hiking are all prime activities in the warmer seasons (if you have the stamina, the five-hour round-trip hike to Giant Ledge and Panther Mountain offers especially rewarding views). The Phoenicia International Festival of the Voice usually takes place in late July/early August, bringing together a captivating program of vocal performances ranging from gospel to opera, world music and musical theater.

Many New Yorkers make the trip here with a single goal in mind: to indulge in the delightfully caloric fare at Phoenicia Diner, a 1962 Greek diner that was transported to the Catskills from Long Island in the 80s. The recently renovated and reopened Sweet Sue’s is also a sure bet for good nosh, but it’s cash only (luckily, there’s an ATM across the street if you get caught out).

Though its roots lie in its namesake town, Phoenicia Flea is now a self-proclaimed “nomadic market of makers and merchants” and takes place in different towns throughout the Catskills (check the website for locations). Another key draw for New Yorkers, the gathering of vendors from the region offers up everything from vintage clothing to apothecary items and handmade furniture.

Where to bed down in the Catskills

You’re almost spoiled for choice when it comes to finding lodgings in the Catskills. For the traditional lodge experience, Deer Mountain Inn sits tucked on a hillside above Tannersville and features six rooms, plus two nearby cottages with four rooms each. The inn’s restaurant recently got a revamp and is now helmed by Michelin-starred chef Ryan Tate, whose seven-course tasting menu is a must for foodies.

Prospect, the restaurant and bar at Scribner’s Catskill Lodge in nearby Hunter is another one to add to your gustatory bucket list. The sleek 'alpine modern' design of the 38-room boutique hotel makes it a preferred weekend pied-a-terre for Brooklynites, who enjoy kicking back aprés-ski in its lobby lounge around the stovepipe fireplace (the hotel has direct views to the slopes of Hunter Mountain). Phoenicia also has its own set of boutique lodgings at the Graham & Co., which includes a badminton court and swimming pool, as well as free access to bikes for exploring the area.

A little further east at the tip of the Ruth Reynolds Glunt Nature Preserve on the bank of the Hudson River, the Saugerties Lighthouse (which is temporarily closed) is an especially charming stay. The restored red-brick building not only houses a museum, but also a bed and breakfast that welcomes guests Thursday to Sunday year-round (be warned that there is no air-conditioning in summer). Climb up to the fully operational light tower for panoramic views of the Catskill Mountains and the Hudson Valley.

Make the escape

Unless you’re looking to hike (as a general rule, most trails are accessible only from April to late October), there’s really no bad time of year to visit the Catskills. Though you’ll need to rent a car to truly experience all that the area has to offer – bucolic one-street hamlets, artist enclaves, glorious waterfalls, and sweeping mountain views – it’s well worth it if you’re seeking refuge from the urban bustle.

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