And North Date Night Guide: Winter 2017

Upstate New York is incredibly romantic any time of year, but winter feels especially ripe for intimacy, not to mention well-timed for an amorous escape north. This is why, for Valentine’s Day, we thought we would propose five excellent date nights to be had up in the mountains with your main-squeeze. Circling around five of our favorite towns — Beacon, Kingston, Woodstock, Phoenicia, and Hudson — our guide points to recommendations on where to stay, eat, drink, explore, and rendezvous. Whether hibernating under cozy white linens in a renovated 19th-century church in Kingston, hiking the snowy path to Kaaterskill Falls, or snuggling up at the single-screen movie house in Woodstock, this list has the perfect mix of love-filled activities for you to enjoy with that special someone. Let us know what you and your honey discover with #andnorthweekend.

Upstate NY Date Night Guide: Winter 2017.
Upstate NY Date Night Guide: Winter 2017.

Travel 90 minutes outside the city to hole up at The Roundhouse, a former textile factory turned posh hotel overlooking the dramatic falls of Fishkill Creek. Set in the heart of Beacon, this dreamy hotel is the perfect base from which to explore the environs of local shops, markets, galleries, and restaurants, a few of our favorite shops being Reservoir, Hudson Beach Glass, and Ella’s Bellas. Spend a quiet afternoon wandering Dia:Beacon, a renowned contemporary art museum on the Hudson River lit by skylights and filled with exhibitions and collections from acclaimed modern artists from around the world. If small-batch spirits are your pleasure, mosey over to Denning’s Point Distillery during tasting hours before dining at The Kitchen Sink, a quaint eatery featuring an eclectic menu of farm-to-table fare, its produce delivered straight from the owner’s family farm. Flirt the night away at Dogwood, a lively neighborhood bar just down the street from the hotel, offering live music, craft brews and cocktails.

Stay: The Roundhouse
Eat: The Kitchen Sink
Drink: Dogwood
Explore: Dia:Beacon
Rendezvous: Denning’s Point Distillery

Beacon, NY
74 miles from New York City

Photos by Tom Moore, Sarah Tew, and Tim Lasalle

Upstate NY Date Night Guide: Winter 2017.
Upstate NY Date Night Guide: Winter 2017.

Travel to Kingston for a stay in one of the beautiful bedrooms of Church Des Artistes, a renovated 19th-century church turned bed and breakfast, owned and run by a composer and artist couple who just so happened to meet on Valentine’s Day. The house is just up the hill from the galleries, shops, marina, and restaurants of the Rondout, and a 20-minute drive from the neighboring towns of Woodstock, Rhinebeck, and Rosendale. Celebrate self-love with a visit to Love & Citrine, a new beauty and wellness boutique that will take extra special care of you. Take the scenic drive to The Rosendale Trestle for breathtaking views of Rondout Creek as well as Joppenbergh Mountain, the Binnewater Lakes, and the Gunks. Later, warm your bones at Brunette with wine and savory snacks as a precursor to elegant comfort food and cocktails at Boitson’s.

Stay: Church Des Artistes
Eat: Boitson’s
Drink: Brunette Wine Bar
Explore: Rosendale Trestle
Rendezvous: Love & Citrine

Kingston, NY
98 miles from New York City

Photos by Katie Lobel and Emma Tuccillo

Upstate NY Date Night Guide: Winter 2017.
Upstate NY Date Night Guide: Winter 2017.

Discover all that Woodstock has to offer with a charming stay at one of the Woodstock Way cottages, hidden away from the bustle of town, yet walking distance to every restaurant, gallery, shop, music venue, and theater in the area. Set off to hike the picturesque trails of Overlook Mountain, the southernmost peak of the Catskill Escarpment and the site of the beautifully eerie Overlook Mountain House ruins. Indulge in delicious pizza and pasta at Cucina, a modern Italian restaurant set in a stylish restored farmhouse, then catch a flick at Upstate Films at Tinker Street, one of our favorite single-screen movie theaters north of the city. Get cozy over nightcaps at Station Bar & Curio, an old 1900 Ashokan railroad station lovingly transported to Woodstock over forty-five years ago on a flatbed truck before heading back to your secluded cottage to tuck in for the night.

Stay: Woodstock Way
Eat: Cucina
Drink: Station Bar & Curio
Explore: Overlook Mountain
Rendezvous: Upstate Films at Tinker Street

Woodstock, NY
108 miles from New York City

Photo by Cindy Halliburton and Cucina

Upstate NY Date Night Guide: Winter 2017.
Upstate NY Date Night Guide: Winter 2017.

Escape to Phoenicia, a tiny but tight-knit hamlet in the town of Shandaken, which runs along Route 28. We suggest reserving a room at The Graham & Co, a stylish modern getaway inspired by the classic Catskills motel, located just a few blocks away from the shops and restaurants of Main Street. Start your morning off with breakfast at Phoenicia Diner, a landmark eatery serving “farm-to-counter” diner-style food in the shadow of Slide Mountain. Afterwards, head to Kaaterskill Falls to revel in the natural wonder of one of the tallest waterfalls in New York State. For some much-deserved pampering, book appointments at The Windham Spa, the perfect place to rest and relax in the heart of the Catskill Mountains. Make merry with cocktails at Scribner’s Prospect, the hotel’s Alpine-inspired restaurant and bar, where floor-to-ceiling windows serve up one of our favorite mountain views.

Stay: The Graham & Co
Eat: Phoenicia Diner
Drink: Prospect at Scribner’s Lodge
Explore: Kaaterskill Falls
Rendezvous: The Windham Spa

Phoenicia, NY
122 miles from New York City

Photos by Sidney Bensimon, Paul Ober, and Natalie Chitwood

Upstate NY Date Night Guide: Winter 2017.
Upstate NY Date Night Guide: Winter 2017.

If a car is hard to come by, consider a scenic train ride up to Hudson, an old whaling town famous for its 19th century architecture and dynamic artist community. Make your way to the top of mile-long Warren Street to check in at Rivertown Lodge, a former 1920s movie house turned upscale hotel with a focus on local craftsmanship. Stroll the downtown streets and treat your boo to gifts from a few of our favorite shops, such as Hawkins New York, Red Chair, Flowerkraut, and 2 Note. For a romantic excursion, tour the stunning grounds of Olana State Historic Site, home and studio of the esteemed Hudson River School painter, Frederic Edwin Church. Whet your appetite with hand-crafted cocktails at WM Farmer and Sons before walking over to Fish & Game, a nose-to-tail restaurant featuring tasting menus that read like ever-changing love letters to the season. End the night at a comfortable table for two listening to live music at Club Helsinki, a beautiful performance venue housed in an old industrial warehouse.

Stay: Rivertown Lodge
Eat: Fish & Game
Drink: WM Farmer and Sons
Explore: Olana State Historic Site
Rendezvous: Club Helsinki

Hudson, NY
128 miles from New York City

Photos by Emma Tuccillo and Christian Harder