A Family-Friendly Getaway in New York’s Hudson Valley

the roundhouse - hudson valley family vacation
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Just a few hours north of Manhattan, New York’s Hudson Valley is a sprawling, diverse, outdoor playground. While many cut through on the way to skiing Windham or Hunter, a scratch below the surface reveals towns and cities with compelling reasons to stick around. For families, the short ride means more time crushing activities and less time dealing with impatient backseat drivers.

Dutchess County

About 800 square miles—or about the size of Jacksonville, Florida—Dutchess includes popular cities, like arty Beacon which straddles the Hudson, and smaller historic village like Rhinebeck. This chunk of the Hudson Valley is easy to reach by car or train for a long weekend.

Where to Stay:

The Roundhouse
Courtesy The Roundhouse

The Roundhouse
Originally a textile manufacturing factory, this rambling, brick-building campus was converted into a 51-room boutique hotel in Beacon is the perfect setting to explore the town. It embraces the area’s rough around the edges of blue-collar history but with fresh, modern touches—think rough plank wood walls with sleek bathroom fixtures and mid-century modern furnishings. The town’s Main Street is a short walk away, as is the hotel’s restaurant. The breakfast here is worth getting up for: You’ll catch views of the Fishkill Creek that spills through the massive floor to ceiling windows and there’s a good chance you’ll have some bread pudding with morning coffee. [From: $229; roundhousebeacon.com]

Eat + Drink:

Kitchen Sink Food & Drink
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Kitchen Sink Food & Drink
Sitting in the banquet in the front of the Kitchen Sink, the scene overlooking Main Street, and much of what’s inside, could be mistaken for the trendiest spot in Brooklyn. A lot of the menu here comes from local farms or what the family grows, but that doesn’t mean it’s for a salad crowd. The dishes here tend to be more comfort food and the fried chicken on Mondays is worth the wait. If you can, grab a seat under the trees in the back. The restaurant is closed on Tuesday, as are a few of the other shops along Beacon’s main strip. [kitchensinkny.com]

Bread Alone
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Bread Alone Bakery
What’s a quintessentially colonial town—one with America’s oldest inn—without a place to carbo-load? Bread Alone’s loaves are in Whole Foods, but its Rhinebeck location is way more than just organic sandwich fodder. The café in the back has simple, but well-prepared breakfast and lunch dishes, from brioche French toast to an impossibly crusty veggie banh mi. A good chunk of the menu is sourced from purveyors around the Hudson Valley. Grab a window seat if you can for some people watching, then snag a brioche roll on your way out—a better coffee mate than you might think. [breadalone.com]

Market St
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Market St.
The small plate dishes and pizzas here run the gamut of Italian-American takes, most of which come out of wood-fired pizza. From the large booths, you’ll see small, nicely charred pizzas fly by all night long. The dishes here are simple, but they rely on seasonal ingredients, so the menu is constantly in flux. Nibble on a snack, or double down with a full-on multi-course meal. The staff here is attentive, and the vibe is hopping with two bars. Desserts like the butterscotch budino is worth saving room for, but if you’re the sort that likes to stretch your legs before sweets, walk over to nearby Samuel’s Sweet Shop, an old-fashioned candy shop, that’s open until 8 p.m. [marketstrhinebeck.com]

What to Do:

Dutchess County Fair
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Dutchess County Fair
For a week each August the fairgrounds in Rhinebeck hosts an epic fair that’s the second-largest in New York State. Nearly 150 acres are filled with carnival rides and funnel cake vendors, but with a heavy dose of agricultural and horticultural exhibits—which is how it started with farmers back in 1845. There’s enough here to keep a family busy for a whole day, including a zoo, indoor shopping pavilion, a Dock Dog competition, and legendary 4H milkshakes. This fair is a tradition for locals, though it continues to change with events like the SporkRun, a competition where contestants create new, and sometimes odd, dishes to serve. [Adult $15, kids 11 and under free; dutchessfair.com]

SplashDown Beach
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SplashDown Beach
This family-friendly waterpark has about 15 attractions, most of which hit the sweet spot of not-too-scary (though the Megalodon is a thrilling multi-person ride). Wait times here are manageable in a 19-acre, compact, well-maintained park. Large groups, or those planning to spend the day, should look into setting up a home base in one of the cabanas (from $110), which includes a locker rental and wait staff taking orders. Wrist bands have a bar code that opens the lockers automatically, which makes it easy for kids to use. You’ll need to bring your own towels though. [From: adults $34; kids $27; splashdownbeach.com]

Walkway Over The Hudson
This 1.28-mile bridge is the longest elevated pedestrian walkway in the world, with epic views of Poughkeepsie and Highland as it straddles the Hudson 212 feet below. With easy access on either end, this is the spot for a morning run or evening stroll. Part of the New York Empire Trail that’s scheduled for completion in 2020, this stretch of the walking- and bike-friendly route will connect Manhattan north to the Canadian border and westward to Buffalo. [walkway.org]

Westchester County

This 500-square-mile area just north of New York City is loaded with museums, galleries, and fine dining. For families, there’s a lot to stick around for that embraces the outdoor space.

Where to Stay:

Hilton Westchester
Boutique hotels have their place, but sometimes the familiarity of a chain is a better bet—especially one that’s perfectly situated near interstates that get you across the county quickly. The staff here is helpful—even offering tips on where to score the best ice cream in town at nearby Bona Bona. Families can kick it in the indoor or outdoor pool, but there’s also a trail snaking through the 37-acre property, through mostly manicured gardens and wooded landscapes. A good portion of the rooms here have been recently renovated. [From $267; hilton.com]

Eat + Drink:

Half Moon
Courtesy Half Moon

Half Moon
Cutting through Dobbs Ferry and situated on the banks of the Hudson, Half Moon’s bank of massive windows offer clear water views. Highlighting seafood from Montauk, Long Island, the menu is diverse enough for families with picky eaters—even in the absence of a children’s menu, we found solid options like a Panzanella salad and well-executed burgers. The sprawling restaurant has a mixed-age crowd in a modern interior that’s open and spacious. The ice cream sandwich here is a guilty-pleasure showstopper with four scoops separated by crispy phyllo layers, topped with whipped cream and berries. [halfmoonhudson.com]

Fin & Brew
Courtesy Fin & Brew

Fin & Brew
Upstairs from the fun and playtime at Spins Hudson entertainment complex, this seafood-forward restaurant is no joke, with a beer menu to match from River Outpost Brewing. Overlooking the Hudson, the restaurant’s vibe has an industrial feel with most seats near a window or on an outdoor deck; a central bar has TVs. Most of what’s served here is made in-house, even things like sausage, but you will have to work a little harder to feed picky eaters here. This was the best food we found over the entire trip, especially the interesting and complex fishermen’s stew. [finandbrew.com]

What to Do:

Sleepy Hollow Cemetery
This is one of those seasonal experiences that comes to life in the fall, especially around Halloween. Tickets for October events range from child-friendly stories to events for grown-ups at one of the most famous cemeteries in America. If you visit out of season, you can still swing by and visit the graves of some real heavy hitters like Washington Irving himself, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller. [sleepyhollowcemetery.org]

Faraway Farm
Courtesy Faraway Farm

Faraway Farm Alpacas
Just a scant 40 miles away from the city, the farm Leda Blumberg and Steve Cole run feels like another world. Teaming with about 20 alpacas, many of which have won awards for their prized fiber, along with horses and a pair of rescue donkeys, the couple runs educational farm tours when they’re not hosting magazine and wedding shoots. Getting up close with the alpacas, many of which have names inspired by famous rock songs, is really a unique experience. Bonus: The headband and scarf we picked up at the shop are as soft and comfortable as any merino we have. [farawayfarmalpacas.com]

Spins Hudson
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Spins Hudson
We’ve never seen anything like Spins Hudson: a 40,000-sq. ft. indoor and outdoor adventure facility tucked into an industrial warehouse that includes a video arcade, virtual reality shooter, two-story laser tag arena, bar, two-story rock walls, and an impressive aerial rope course. The aerial rope course here is intense with three stories of varying obstacles. Climbing requires learning a magnetic clipping system that takes some getting used to, which you’ll do inside. Then when you’re ready, take it outdoors and, if you make it to the top, you’ll be rewarded with killer views of the Hudson. [From: $5; spinshudson.com]

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