Ultimate Guide to a Memorable Catskills Weekend Getaway

Escape to the Catskills: A Nature Lover’s Retreat

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 the independent bookstore The Golden Notebook for some vacation reading material. Yum Yum offers creative takes on Japanese noodle bowls and Southeast Asian street food, while the locals’ favorite Cucina serves up Italian dishes in a restored farmhouse. 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.

ornate red-and-white monastery in Woodstock, New York
The wilderness around Woodstock holds many surprises, including this Buddhist monastery © Sam Aronov / Shutterstock

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 encounter the mountain house ruins, a historic fire tower, and a Buddhist temple on your journey, not to mention some 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 attracted painters from the Hudson River School, who captured the unique landscape on canvas. Circle W, the town’s general store, has serviced locals since 1908. Since being saved from the wrecking ball in 2009, it has evolved to cater to city-slicker visitors, offering hearty breakfasts and lunches, great coffee, chai, matcha lattes, and local maple syrup.

Palenville is also a great base for exploring 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. Fawn’s Leap waterfall is a well-loved swimming spot in the warmer months.

pink wooden storefront in Tannersville, New York
Colorful Tannersville offers a range of browsing options for visitors © Mikki Brammer / iBestTravel

Get Some Color in Tannersville

Not to be outdone by Palenville, Tannersville bills itself as “the painted village in the sky,” referring to the cheerful rainbow palette of the architecture on its main street where you’ll find a wide selection of quirky stores. When hunger strikes, stop by Maggie’s Krooked Cafe – a local staple for more than 30 years – or the newcomers Mama’s Boy Burgers and Mama’s Boy Pizza. To burn off the calories afterward, the 4.4-mile walk to Inspiration Point and Boulder Rock Trail ranks among the area’s best hikes.

Earn Your Calories in Phoenicia

A sleepy yet picturesque hamlet perched on the banks of Esopus Creek about 20 minutes from Tannersville, Phoenicia is a beloved getaway for outdoor enthusiasts. Cross-country skiing and snowshoeing are the draws in winter, whereas fishing, tubing, and hiking are prime spring and summer activities. 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, featuring a captivating program of vocal performances across various genres.

diner counter set for customers
Phonecia Diner has retained its vintage look and feel © Mikki Brammer / iBestTravel

Many New Yorkers make the trip here with a single goal: to indulge in delightful meals 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 great choice for delicious food; however, it’s cash only (an ATM is conveniently located across the street).

Although its roots lie in its namesake town, Phoenicia Flea is now a self-proclaimed “nomadic market of makers and merchants” taking place in different towns throughout the Catskills. This gathering of local vendors offers a plethora of goods, including vintage clothing, apothecary items, and handmade furniture.

Where to Bed Down in the Catskills

You’re almost spoiled for choice when it comes to finding places to stay 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 has recently been revamped and is now helmed by Michelin-starred chef Ryan Tate, whose seven-course tasting menu is a must for foodies.

rustic wooden inn against a blue sky and snowy ground in New York
The Deer Mountain Inn is both a cozy retreat and a dining destination © Mikki Brammer / iBestTravel

Prospect, the restaurant and bar at Scribner’s Catskill Lodge in nearby Hunter, is another one to add to your culinary bucket list. The sleek “alpine modern” design of the 38-room boutique hotel makes it a preferred weekend getaway for Brooklynites, who enjoy unwinding aprés-ski in its lobby lounge around the stovepipe fireplace. Phoenicia also has its own set of boutique lodgings at the Graham & Co, which include 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 a 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 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. Although renting a car is necessary to explore 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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