Art, Hiking, Food and Drink Shine in A Trip Through the Hudson Valley Art, Hiking, Food and Drink Shine in A Trip Through the Hudson Valley

Less than an hour north of New York City, as you cruise Highway 9 along the Hudson River, the landscape starts to shift. It’s subtle at first: The tug-of-war between trees and buildings begins to tip in favor of the trees. Urban hustle is replaced by dramatic cliff faces, undulating swaths of green, a soft draping of light that makes it easy to see why the Hudson River School painters and New York elite obsessed over this landscape.

But on the other hand, to romanticize the Hudson Valley as simply a place of retreat from the city is to miss the communities that thrive here. Stretching along the river from Westchester County to Albany, the Valley encompasses more than 7,000 square miles that are impossible to cover in a short visit. But to trek from Cold Spring to Kingston is to be steeped in the region’s art, nature, agriculture and industry—all the factors that shaped this place—as well as the vibrant, thoughtful endeavors that carry it forward today.

MILES: 14
CAFFEINATE: COLD SPRING COFFEEHOUSE, COLD SPRING
READ: SPLIT ROCK BOOKS, COLD SPRING
DRINK: FLOWERCUP WINES, COLD SPRING

Culminating at the river and a conveniently walkable train station, Cold Spring charms as a perfect jumping off point to access the natural world and art heritage that make the Hudson Valley so alluring. The 15-minute drive north toward Beacon hits notable trailheads and landmarks.

Hudson Valley & Catskills

Art stops and antique shops, historians and filmmakers, small-town delights and Catskills wonders.

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Magazzino Italian Art: An impressive collection of post-war and contemporary Italian art, with a focus on the Arte Povera movement, this bright renovation of a former computer chip warehouse sits on expansive grounds, including walking trails and actual Sardinian donkeys.

Bannerman Castle: Take a boat to a curious and elaborate abandoned military surplus warehouse located on Pollepel Island, maintained by the Bannerman Castle Trust, which offers walking tours. Book in advance.

Breakneck Ridge: Commanding vast and impressive views of the river, this trail loop is occasionally difficult (not the best for kids). Easy parking and trail maps available at the trailhead.

Tironda Hat Works Factory: Burned down and abandoned, this former hat factory is a graffiti-covered wonder in Madame Brett Park, just south of Beacon among 12 acres of woodland and marshland trails. Hats were big business in the mid-19th century and many defunct factories have been repurposed (such as Roundhouse, Beacon).

MILES: 49.6
SHOP: LITTLE KING, BEACON
LUNCH: ZIATUN, BEACON
ADORN: IRWIN GARDEN, RHINEBECK

Beacon was once defined by its industrial manufacturing might (including hats!). But the opening of Dia: Beacon in 2003 reinvigorated the town-like city. Main Street now features eclectic restaurants, boutiques and some of the best contemporary art in the HV. The longest stretch of this road trip feels almost like reversing time—ultimately to Rhinebeck, once a seat of revolutionary and political significance, still a well-resourced, bucolic and historic village.

Dia:Beacon: The jewel of Beacon, this Dia Art Foundation site is located in a former Nabisco box printing factory and features art from the 1960s onward, including works of staggering scale from significant names like Richard Serra, Louise Bourgeois and Sol Lewitt, plus exceptional programming.

Burger Hill: It’s a steep, long hike up, but the view and sense of accomplishment are gold. In the winter this is a secret sledding darling.

‘T’ Space: Nonprofit art gallery which functions as the library and archive of architect Steven Myron Hall, replete with poetry readings, performances, and residencies. EDITOR’S NOTE: The author can’t say this because she owns the place, but we don’t mind recommending a pause for a weekend cocktail at C. Cassis, just down the road.

Beekman Arms: In the center of Rhinebeck, this is the oldest continually operated inn in the U.S., and walking through the doors for a seat at the tavern bar ensconced in dark wood is like entering a portal.

MILES: 11
WATCH: UPSTATE FILMS, RHINEBECK
LIVE MUSIC: TUBBY’S, KINGSTON
SNACK: ROSIE GENERAL, KINGSTON

Fruit and winegrowing have long been central to the area (purportedly the oldest grape-growing region in the U.S.); exploring local cideries, wineries and breweries opens a window into this agricultural history.

Crossing over to the other side of the river, Kingston feels more nebulous than other Hudson towns. There isn’t just one epicenter, but a few distinct areas that exude breezy buzzing energy: Broadway, Stockade, Rondout.

The point is, there’s a lot here, and you’d be well-served to hang around, starting with a few of the spots here.

Slow Fox: A vegetable and flower farm coupled with a thriving brewery and tap room and an impressive array of beers.

Rose Hill: Sprawling orchards offering pick-your-own apples, farm stand and tap room featuring draft pours of their own exceptional ciders, plus a well-stocked bottle shop of other stellar local producers, like Rhinebeck favorite Branchwater Distilling.

Eliza: Flawless food, wide-ranging wine list and expert hospitality from the team behind a slew of well-regarded local staples. Down the road from Tubby’s, and another favorite: the Spanish sherry and tapas bar Mirador.

Rough Draft: A book store that’s also a bar? What’s not to love? This is the thing about the Hudson Valley; there’s a romance to the hard work, the history, the region’s growth and decline and growth again, a cycle that loops back repeatedly along the river.

As the tide rises, the river flows north, and as the tide falls, the river flows south. Mohican people who lived here long before European contact named the Hudson “the river that flows both ways.” Whether you are coming or going, this is a place that beckons you to slow down and look around.