Three serene winter getaways in the Hudson Valley

This article is part of FT Globetrotter’s guide to New York

When it comes to defining exactly what is the Hudson Valley, there is plenty of room for debate. Three million acres of varied terrain — rolling hills, quaint towns and small cities — extend from the confluence of the Mohawk and Hudson rivers in northern Albany County down through Westchester County, aka the suburbs of New York City. It is composed of 10 diverse counties and further divided by region: Lower Hudson, Mid Hudson and Upper Hudson. Most people tend to associate bucolic weekend getaways and cultural pursuits with the midsection, but let’s just say the territory is loosely defined.

“The thing about the Hudson Valley is its vastness,” explains life-long resident and food writer Tarajia Morrell. “Tucked into its hills and hollows are villages, each with a distinct character. If you go just one county over, there is a whole new sense of discovery. The commonality is the sylvan beauty that lies between the towns. There really is something for everyone here.”

So whether you’re in the market for snowshoeing, craft cocktails by a crackling fire or stately-home museums rich with American history, there are endless options — and all are just two easy hours from midtown Manhattan.

Dutchess County 

From your base at the charming Troutbeck — an 18th-century former inn and estate that played host to writers such as Ralph Waldo Emerson and Henry David Thoreau and politicians including Theodore Roosevelt — in Amenia, the towns of Wassaic, Millbrook and Millerton are just a 10- to 20-minute drive away. This recently revamped boutique hotel has 37 guest rooms and suites — in all configurations — by designer Alexandra Champalimaud and reads Scandi-intellectual, right down to its cosy libraries and low-lit, convivial bar. The halls are fully decked at the holidays with festive fir-tree bowers, amaryllis and poinsettias, which sets the stage for gingerbread house-making, a Feast of the Seven Fishes-inspired dinner and New Year’s Eve festivities for all ages.

This is firm foodie territory, so expect to start the day with freshly baked cardamom buns and croissants from Vitsky Bakery in nearby Wassaic before popping into the Wassaic Project, an artist-run non-profit gallery and education centre that’s housed in a seven-storey former mill. A visit to Tenmile Distillery, makers of small-batch whisky, gin and vodka, is worth the detour for excellent spirits and a field-to-fork meal by Westerly Canteen that’s served in the idyllic apple orchard in fall.

Further on, the small town of Millbrook is home to Innisfree, a spectacular, undulating garden built between 1930 and 1960 that was inspired by scroll paintings of the 8th-century Chinese poet and artist Wang Wei. Regardless of the season, the series of bogs, berms and rock terraces forms a stunning landscape.

Just down the road (everything is 20 minutes from everything else here) sits Millerton, a quintessentially quaint village with a decidedly Brooklyn-hipster vibe. Score pricey Nordic sweaters and perfect Levi’s at Westerlind or cross Main Street to the newly opened The Dutchess Trading Company — a tasteful curation of French soaps, candles, linens and more. If hunger strikes, the retro Oakhurst Diner does a fine burger or an unexpectedly delicious pho. Cinephiles will love The Moviehouse, which screens arthouse and independent films, as well as live performances from the Metropolitan Opera.

End any day at Stissing House, a former inn and tavern in nearby Pine Plains that dates back to 1782. Chef-proprietor Clare de Boer — an alum of River Cafe in London and co-owner of King in New York — brings simple, fresh dishes including coal-roasted, day-boat scallops with green garlic butter and suckling pig with roasted peaches from nearby Sugar Hill Farm.

Rhinebeck and Tivoli

For the sheer diversity of hotels, restaurants and historic sights — not to mention ease of access via Amtrak — it’s impossible to beat the village of Rhinebeck. At the main intersection in town (it’s a one-traffic-light affair) sits the Beekman Arms inn, with its white-stone façade and black shutters — the same as it has been since its founding in 1766. Nearby, the French-style Mirbeau Inn & Spa is great for hot-stone massages and farm-forward cuisine. A new player is C Cassis, makers of “not very sweet, lightly fermented” blackcurrant liqueur that is best savoured in its bright, bijou tasting room.

Stroll along magically lit Market Street, where Samuel’s Sweet Shop, a candy emporium co-owned by actors Paul Rudd and Jeffrey Dean Morgan, provides an afternoon pick-me-up in the form of a peanut-butter cup blondie, which pairs nicely with a flat white from Bread Alone across the way.

Once properly fuelled, head for Wilderstein (“wild man’s stone”, in reference to an Indian petroglyph on the property), a 19th-century Queen Anne-style country house that sits high above the Hudson river. With landscape design by Calvert Vaux and a storied history that included many visits by FD Roosevelt, this Victorian oasis has guided tours, speaker series, holiday programming and scavenger hunts for kids.

For more festive-season fun, the drive-through Wonderland of Lights (November 28–December 29; check schedule) at the Dutchess County Fairgrounds promises to dazzle.

After a day of activity, dinner at Le Petit Bistro is a well-earned highlight. Craft cocktails, oysters and the perfect steak au poivre all make a meal here memorable. Keep dessert simple and go for an ice-cream cone (the mint brownie swirl is outstanding) at Del’s Roadside, a beloved institution since 1960. 

If you’re looking for a quieter scene, the village of Tivoli — population 1,000 — just up Route 9G is worth a visit. The Hotel Tivoli and its farm-to-table restaurant, The Corner, were started by the late artist Brice Marden and his wife, Helen. It has 12 eclectic, vibrantly coloured rooms and makes for a total weekend escape, and it’s an easy walk to favourite area newcomer GioBatta Alimentari. The pride of chef Francesco Buitoni (of that pasta family), the menu features Italian classics — Caprese salads, bistecca ai ferri (grilled steak) with cannellini beans and tagliatelle Bolognese — at reasonable prices.

Across the river

Due west of Rhinebeck, just over the Kingston-Rhinecliff Bridge, lies the small city of Kingston, a once-sleepy spot that is now home to a thriving arts and culinary scene. In one of the Hotel Kinsley’s beautifully appointed 42 rooms in the historic Stockade District, you’ll have sumptuous surroundings (think velvet banquettes and Frette linens, but in a country way) and easy access to adventure. Hutton Brickyards is another riverfront option, with floor-to-ceiling views from its minimalist pine and glass cabins. 

From either hotel you can easily explore the Midtown Arts District and the Reher Center for Immigrant Culture and History, which is housed in a historic bakery. There’s excellent shopping too: locally handmade furniture and tabletop items with a contemporary sensibility at Black Creek Mercantile & Trading Co, while Hops Petunia does a more colourful housewares edit. For hemp denim trousers and moleskin work jackets, head to Clove & Creek, where you can source an entire weekend wardrobe in one room.

While the surrounding area isn’t known for challenging ski terrain, there are plenty of gentler offerings: Hunter, Belleayre and Windham mountains are all under an hour away and are ideal for beginners and snowboarders alike.

After long days spent outdoors — exploring, hiking, gallery-hopping — comfort food fits the bill. For casual fare, both Ollie’s Slice Shop and Lola Pizza vie for locals’ hearts, while the Italian-inspired Eliza (from the team behind Ollie’s) serves fan favourites — baby gem salads, housemade cavatelli, the perfect burger — in a wonderfully buzzy, retro setting complete with neon signage.

How to get there: Accessible by car on the scenic Taconic Parkway, or by train (Metro-North from Grand Central Station to Wassaic or Amtrak from Penn Station to Rhinecliff, NY)

Do you have a favourite Hudson Valley getaway? Tell us in the comments below. And follow FT Globetrotter on Instagram at @FTGlobetrotter

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