Cold Spring

Whenever we’ve made the journey to Cold Spring, we’ve come dressed in activewear with a backpack full of Clif Bars. This sweet little town, seven miles south of Beacon, is surrounded by hiking trails, including Breakneck Ridge – a steep all-fours scramble to several panoramic lookout points (it’s particularly gorgeous in Fall when the valley rustles with amber and crimson foliage). Once you’ve completed the challenging route, treat yourself to a post-hike carb feast at Cathryn’s, a Tuscan restaurant with a pretty garden for alfresco dining.

Our tip for overnight stays is the Pig Hill Inn, a red brick bed and breakfast with wood-burning stoves, where you can get a massage in your room and enjoy blueberry pancakes in bed. Along the rest of Main Street you’ll find Cold Spring Apothecary, a botanically inclined health and beauty company with an adjoining spa, BURKELMAN, a home and lifestyle boutique run by two former NYC creatives, and a handful of antique stores with goods salvaged from the Hudson Valley.

Woodstock

Thanks to a series of Fyre Festival-style calamities, the Woodstock music festival was actually held in Bethel, 40 miles southwest of its namesake town. Nevertheless, Woodstock still exhibits the bohemian spirit of 1969’s “Aquarian Exposition,” complete with its fair share of tie-dyed clothing and vegan restaurants. 

Make a weekend base in one of Woodstock Way’s beautifully outfitted cabins, or at the Graham & Co., a modern motel that’s a twenty-minute drive away in Phoenicia, but boasts its own outdoor pool and movie projector for summer night screenings. Woodstock is a hub for art of all genres. Find entertainment during the day with a performance at the Woodstock Playhouse, a workshop at The Center For Photography at Woodstock, or a visit to Upstate Films, a single-screen non-profit cinema.

Hudson

Once a prominent whaling town, Hudson’s modern revival began in the 80s and 90s, when artsy types opened galleries and antique shops along its main drag, Warren Street. Since then, the town has continued its trajectory, attracting city-weary New Yorkers with its blend of doorstep nature and Brooklyn-caliber establishments. Many of the residents are, in fact, former Brooklynites who bought and converted historic properties, then turned them into thriving businesses. You can sleep in an old hat shop (The Hudson Milliner) or a former movie theater (Rivertown Lodge), visit a gallery that used to be a bank (BCB Art) or watch opera in a building that once housed City Hall (Hudson Hall).

Narrowsburg

The teeny town of Narrowsburg, snuggled between the Catskills and the Pocono Mountains, is reachable via one of New York state’s most scenic driving routes – a winding stretch of road known as the Hawk’s Nest. It’s also situated on the Upper Delaware Scenic and Recreational River National Park, giving visitors easy access to riverside trails, tubing, and canoeing (Lander’s River Trips is our go-to operator).  

Overnighters should book a room at The Moonriver Inn, a pet-friendly abode composed of four stylish rooms, each decorated with turntables, claw-foot bathtubs, and plush fainting couches. Right from the doorstep, you’ll find a slew of independently owned stores and restaurants lining Main and Bridge Streets. Pick up home decor items curated by a former Vogue design director at Nest, or heirloom antiques from Sunny’s Pop. Then refuel at The Heron, whose southern-style dishes, like cajun catfish bites and fluffy biscuits soaked in gravy, incorporate ingredients from the restaurant’s community of Upper Delaware farmers and artisanal producers.

INTRO: @Roundhouse, courtesy of Hudson Valley Illustrated

BEACON: @Dia:Beacon, courtesy of @mikejowal, @Roundhouse and Denning's Point Distellery, courtesy of Kyran Tompkins

COLD SPRING: @matt.ritchie, @BURKELMAN and @Cold Springs Apothecary

WOODSTOCK: @Graham & Co.

HUDSON: @Hudson Milliner, courtesy of @Shannon Greer

NARROWSBURG: @Sunny's Pop, courtesy of @rachgarb