7 Charming Towns in the Hudson Valley With Outdoor Adventures, Incredible Restaurants, and Local Art

Less than two hours from New York City, the Hudson Valley has long been an easy escape for city dwellers—and you don’t even need a car, with Metro-North and Amtrak trains tracing the river north. Across its nearly 150-mile stretch, the region is studded with small towns that mix history, culture, and natural beauty in ways that feel distinctly their own.

But the Hudson Valley is bigger and more varied than many realize, and exactly what counts as the Hudson Valley depends on who you ask. Using the Hudson River Valley National Heritage Area’s definition (also adopted by I Love NY, the state’s official tourism office), the valley runs much farther north than many visitors realize—all the way past Albany. That’s where the experience shifts; as travel writer and Hudson Valley local Robin Catalano points out, the Upper Hudson Valley is “definitely overlooked, but it’s gorgeous, has much less tourist traffic, and tends to be less expensive than Hudson and points south,” making it well worth a visit.

Still, the entire region has something for all types of travelers—from arts hubs to historic river towns and under-the-radar gems. Ahead, we’re highlighting the best towns in the Hudson Valley, along with what to see, do, and explore, according to local experts.

Hudson

Businesses in downtown Hudson, New York.

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Once a sleepy town, Hudson has reinvented itself as a trend-forward haunt that draws New Yorkers seeking tranquility—yet still hums with a lively energy. A steady wave of city transplants has fueled this transformation, opening antique shops, design studios, and stylish boutiques that now line Warren Street downtown. Food and drink keep pace with the style: Carly Fisher, author of “Easy Weekend Getaways in the Hudson Valley & Catskills,” points to Kitty’s, Talbott & Arding, and MOTO Coffee/Machine for daytime fuel, while Mel the Bakery offers “pastries worth writing home about.” Evenings might mean cocktails at The Hereafter, followed by an Italian-inspired dinner at favorites like The Tavern at Rivertown Lodge or Feast & Floret, with a nightcap at The Maker Lounge. Shopping is as much about browsing as buying, with Fisher noting favorites like Spotty Dog Books & Ale, John Doe Records and Books, Magic Hill Mercantile, Clove & Creek, and the ever-popular Antique Warehouse.

And while Warren Street is the town’s heart, Fisher cautions that “many people miss attractions at the edge of town and beyond that require a car (but are entirely worth the effort).” These include Basilica Hudson, a multidisciplinary art center in a reclaimed factory; Time & Space Limited (TSL), an indie theater for arthouse films and experimental performances; the Olana State Historic Site, Frederic Edwin Church’s hilltop estate with sweeping views; and the Henry Hudson Riverfront Park, a perfect spot to catch sunsets over the water.

Cold Spring

Stores in downtown Cold Spring, New York.

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“Cold Spring is one of those towns that feels like a perfectly wrapped gift—historic streets, river views, and just the right amount of bustle,” says Lisa Karvellas, co-founder of Cedar Lakes Estate in nearby Port Jervis. She recommends stopping at Vera’s Marketplace & Garden Center for “the best-ever cider donuts” before wandering through Cold Spring General to browse home goods and locally made finds. From there, continue along Main Street, where antique shops like Cold Spring Antiques Center and Once Upon a Time Antiques beckon treasure hunters. “For dinner,” Karvellas adds, “I love heading down the river to Dolly’s in Garrison,” which she describes as “cozy, seasonal, and always a little bit special,” with entrees that run the gamut from fluke crudo and spicy Scezuchan shrimp to cauliflower nuggets and crispy chicken sandwiches.

Adventurers and outdoor enthusiasts aren’t left out either: the town is a gateway to some of the Hudson Valley’s most iconic hikes. Breakneck Ridge offers steep, rewarding climbs with sweeping views over the Hudson, while the gentler trails in Hudson Highlands State Park provide equally stunning vistas.

Port Jervis

Aerial view of autumn in Port Jervis, New York.

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Tucked at the point where New York, New Jersey, and Pennsylvania meet, Port Jervis has a character all its own. Karvellas describes it as “a little under-the-radar, which makes it feel extra-special.” She’s also quick to call out the “great energy downtown,” with Fogwood + Fig serving standout vegan comfort food in a hip, plant-filled space, Foundry42 for coffee and locally made gifts, and Fox N Hare Brewing Co. drawing crowds for live music and craft beer.

Beyond the charming downtown, Port Jervis doubles as a gateway to the outdoors. The town sits at the edge of the Delaware River and is minutes from High Point State Park, the Delaware Water Gap, and the Port Jervis Watershed Trails system, beloved for its hiking and biking opportunities. Visitors can also tube or kayak along the Delaware, wander the wetlands of the Bashakill Wildlife Management Area, or even tackle sections of the Appalachian Trail, all within a short drive.

Troy

Historic buildings in downtown Troy, New York.

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The Gilded Age fans will want to add a trip to Troy to their Hudson Valley itinerary. “Located right on the Hudson River, Troy was a powerhouse of manufacturing and contains one of the largest concentrations of Gilded Age architecture in the country. The John Paine Mansion, also known as The Castle, is a prime example,” says Catalano. Today, that historic backdrop mixes easily with a burgeoning culinary scene, which she notes “is growing by leaps and bounds.” For breakfast, she suggests Jacob Alejandro or The Placid Baker for “superb coffee and pastries,” before settling in at The Whistling Kettle for sandwiches and “dozens of teas.” For dinner, she points to Taqueria Tren Maya, where authentic tacos and tostadas bring bold flavors to this riverside city.

Don’t leave town without picking up a few souvenirs, either. Catalano recommends Annick Designs for artisanal jewelry and home goods, Troy Cloth & Paper for art prints, graphic tees, and stationery, and Ekologic for upcycled, handcrafted garments. If you’re visiting on a Saturday, make time for the Troy Waterfront Farmers Market, one of the largest in the state. Running year-round, it’s a showcase for local produce, baked goods, and handmade crafts, all set against the backdrop of the city’s Gilded Age streetscapes.

Kinderhook

Entrance to a store in Kinderhook, New York.

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Located in Columbia County near Hudson, Catalano describes Kinderhook as “an absolute gem of historic architecture, picturesque neighborhoods, and sweet shops and cafés.” The 750-mile-long Empire State Trail runs right through the village, making it a natural draw for cyclists and walkers. Just off the route sits the Persons of Color Cemetery, a storied site that preserves the little-discussed legacy of slavery in the North.

Today, the village strikes a balance between its historic roots and a growing arts and culinary scene. For culture, book a slot to visit The Jack Shainman Gallery: The School, which Catalano calls “an exceptional adaptive-reuse project based in a once-abandoned 30,000-square-foot high school.” After, tuck into a hearty Lebanese lunch at Hamrah’s before browsing the boutiques inside the Kinderhook Knitting Mill.

Catalano also recommends sticking around for dinner at The Aviary, “which serves top-notch cocktails and inventive recipes inspired by the Hudson Valley landscape,” like grass-fed beef burgers, slow-roasted sweet potatoes with bacon, and potato croquettes topped with smoked trout roe. If you’re staying overnight, reserve a room at the Old Dutch Inn, which Catalano describes as “an antique-meets-modern stay run by the same family behind Samascott Orchards and Farm Store, right in the center of town.”

Beacon

Main Street in Beacon, New York.

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Easily reached by train from New York City, Beacon has become one of the Hudson Valley’s most talked-about towns, anchored by Dia Beacon, the massive contemporary art museum housed in a former Nabisco box-printing factory. Beyond the museum, the town boasts a buzzy Main Street lined with galleries like BAU (Beacon Artists Union), breweries like  Hudson Valley Brewery and Two Way Brewing Company, and boutiques including Hudson Beach Glass, set in a restored firehouse, and Hyperbole, known for quirky gifts and locally made pieces. Right in town, Fishkill Overlook Falls adds natural drama as it cascades beside the Roundhouse, an industrial-chic boutique hotel and restaurant housed in a restored factory.

Kingston

Aerial view of Kingston, New York.

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With its colonial stone buildings, converted warehouses, and revitalized arts scene, Kingston feels like the Hudson Valley’s small-scale answer to Brooklyn. Once the first capital of New York, the city is divided into three districts. Uptown’s Stockade Historic District is lined with 17th-century stone houses and restaurants, while Midtown is home to galleries and performance spaces. Down by the Rondout waterfront, warehouses have been reimagined as boutiques, bars, and museums, and a riverfront park and promenade connect to the Hudson River Maritime Museum and Hudson River Cruises—one of the city’s most scenic spots.

Downtown, Kingston balances shopping, food, and culture with ease. I browsed Hamilton & Adams for locally made apparel, then wandered into a few boutiques before ducking into Rough Draft Bar & Books, an indie bookstore–café–bar where I paired a flaky croissant and latte with some laptop time. Nearby, I checked into the boutique Hotel Kinsley, which spans several historic buildings across Uptown. Its flagship, a former State Bank of New York, still has the original steel vault door leading into a sleek, art-filled lobby. Downstairs, Restaurant Kinsley serves a seasonal menu of New American fare, including mushroom tacos and smashburgers, in an art-filled space. Next time I’m in town, though, I’ll be making a beeline for Sorry, Charlie, a vibey neighborhood spot acclaimed for its crispy bar pies.