6 Cool Towns to Visit in the Hudson Valley

With roadside farm stands, historic markers, scenic overlooks and hiking trails dotting a river-, mountain-, and valley-studded landscape, New York State's pastoral Hudson Valley region promises plentiful points of quiet refuge. And, perhaps more unexpectedly, the area also dishes out a big, heaping serving of country-style cool. Part countryside, part urban outpost (with Manhattan averaging distances of just about 90 minutes away), nature, culture, and creativity converge here to smashing effect, with the Hudson Valley hip factor off the charts in several revitalized and energized enclaves.

Forget hipsters: here, "hicksters" freely roam. Creative, interesting denizens, joined by an increasing infusion of NYC transplants, are producing food, art, culture, and inventive entrepreneurship. In the following six leading Hudson Valley capitals of cool, you'll be spoiled with choice for locavore eateries, chic new hotels, imaginative boutiques, and cutting-edge cultural venues – most of which come clustered within the converted hodgepodge of historic architecture (ranging from old factories to reinvented farmhouses) that line the main drags of these small cities and towns.

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View of the Hudson from Kingston
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Set between the Catskill Mountains and Hudson River, this Hudson Valley city—spread out across three main districts: Uptown, Midtown, and Downtown—can certainly claim staying power, with its colonial-era roots dating back to the 17th century, and standing as the first capital of New York (which earned it a good torching from the British during Revolutionary War days). Today, Kingston's history and politics play second fiddle to the budding arts and entrepreneurial renaissance unfolding there, with creative energy spilling about town at breakneck speed.

In Uptown—anchored on the historic Stockade District—charming old buildings (like the 1852 Old Dutch Church and 1676 Senate House) intermix with large-scale murals (mainly leftovers from the city's annual fall arts-and-music-packed O+ Festival) and happening spots like live music venue BSP Kingston, set within an early-1900s vaudeville theater. A string of linger-worthy music stores and bookshops like Rhino Records, Rocket Number Nine Records, and Half Moon Books meet locals' favorites for dining and imbibing. Try town hub and standout coffee shop, Outdated, Diego's for inventive Mexican fare, and Stockade Tavern for well-crafted cocktails.

New galleries and intriguing artist live-work spaces (like the Shirt Factory and The Lace Mill) abound in the burgeoning Midtown Arts District (MAD), an organization of some 200 arts-based businesses that are inhabiting dozens of old industrial buildings throughout the Midtown neighborhood. Visit during First Saturdays, when many of MAD's members open their doors to the public during ongoing first-Saturday-of-the-month receptions. 

Downtown (also known as the Strand, or the Rondout) offers a more maritime-minded vibe perched alongside Hudson River tributary Rondout Creek. Pop into the Arts Society of Kingston (ASK) for rotating gallery shows and performing arts events; throw back a glass of vino at the Brunette wine bar; or pop into the Clove and Creek boutique, showcasing crafts and home goods from local makers. Nearby, the seasonal Brooklyn-spinoff Smorgasburg Upstate debuted in 2016, bringing gourmet food stands and live music to the historic Hutton Brickyards. Base your stay here at the stylish Forsyth bed and breakfast, or keep your eyes peeled for a handful of new boutique hotels in the works in Uptown, too.

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Olana, Persian-style Home of Frederic Church
Terryfic3D/Getty Images

While other Hudson Valley urban centers are on the rise, the riverside city of Hudson has definitively arrived, a long-established darling of national travel publications and NYC second-homers. Its ascent from a centuries-old whaling center to an antiquing hub to a thriving arts center has drawn with it a steady stream of newcomers, lured in by Hudson's charmingly diverse architectural inventory, and robust dining, shopping, and cultural offerings.

Much of the activity comes anchored on the city's main strip, Warren Street, where foodies flock to lauded restaurants like Swoon Kitchenbar and Cafe Le Perche, along with unique watering holes like bar/bookstore hybrid Spotty Dog Books & Ale. On the shopping front, antiquing still thrives in emporiums like Hudson Supermarket, while more funky modern boutiques are peppered in, like Flowerkraut, a florist that serves up an unexpected side of fermented vegetables.

Come nightfall, music venues and event spaces like Club Helsinki, Basilica Hudson, and the Hudson Opera House showcase top talent. Just south of town, 19th-century Hudson River School master painter Frederic Church built his Moorish-styled personal estate at Olana; it's open for tours and offers miles of verdant trails. There's no shortage of stylish Hudson hotels at which to base a stay: Try WM Farmer and Sons or Rivertown Lodge for some of the hippest digs.

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corner interior of Dia:Beacon

Rapidly transformed, this former gritty mill town has been firmly reinvented as an in-demand artsy community—with the pricey real estate to match—thanks in large part to its proximity to Manhattan, to which Beacon is connected with an express Metro-North train. Main Street traces the small city's spine, where boutique shops beckon (try Dream in Plastic for quirky gifts or Hudson Beach Glass for blown-glass items and demos), along with buzz-garnering eateries (like Homespun Foods, Kitchen Sink Food & Drink, or the kitschy Doctor Who-themed restaurant, The Pandorica).

Beacon's cultural heavyweight is the expansive contemporary Dia:Beacon museum, set within a former Nabisco printing plant on the banks of the Hudson, and now featuring large-scale works from the likes of Sol LeWitt, Richard Serra, and Louise Bourgeois. Music lovers can tune into regular jams at the Towne Crier Cafe, while nature enthusiasts can hit up hiking trails to Mount Beacon right from the heart of town. Looking for a home base? Try the industrial-chic Roundhouse, a former factory-cum-hotel complex overlooking Beacon Falls. 

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New Paltz

New Paltz street
Christine Ashburn

Infused with the intoxicating energy of youth, as is standard per any college town (this one's home to liberal arts college SUNY New Paltz), the town of New Paltz—with its longstanding bohemian and countercultural roots–ups the ante with an obvious appeal for adults beyond their college years, too. Nestled at the foot of the Shawangunk Ridge (aka "the Gunks"), this lively little town scores big points for active types, touting some of the best rock climbing east of the Mississippi River, as well as easy access to hiking and/or biking trails within the Wallkill Valley Rail Trail or nearby Minnewaska State Park or Mohonk Preserve.

In the heart of town, much of the hustle-and-bustle runs down and along offshoots of Main Street, where cool bars (try Bacchus, Jar’d Wine Pub, or Huckleberry), head shops, and coffee shops (like the Cafeteria Coffee House), fill in the gaps between enticing eateries—Main Street Bistro, Mexican Kitchen, Garvan's, and A Tavola Trattoria rank tops. History lovers should sneak a peek at the colonial-era stone houses along Historic Huguenot Street, billed as the oldest street in America. Another historic spot, that's well worth the splurge, is a stay at the superlative, all-inclusive Mohonk Mountain House—dating back to 1869, this Victorian castle-hotel affords world-class accommodations.

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Glowing neon of diner sign in Millerton, New York
Barry Winiker/Getty Images

If cool coffeehouses, indie theaters, and treasure-packed old bookshops comprise your idea of a cool town, than the old railroad hub of Millerton—situated close to the Connecticut border—has got you covered. Fuel your stroll along its walkable Main Street with a caffeine pit-stop at the Irving Farm Coffee House (with coffee that comes freshly roasted from their nearby roaster), or at the transporting Harney & Sons teahouse, complete with a tea tasting room, tea lounge, and gift shop. Book- and music-lovers can pop into Oblong Books & Music (it's been there since 1975), while cinephiles flock for flicks at The Moviehouse, showing first-run and indie films. Chow down at neighborhood favorites like the retro Oakhurst Diner, 52 Main (serving tapas), or Manna Dew Café (plating New American dishes).

Active types can hit up the Harlem Valley Rail Trail right from the heart of town, for close to 11 miles of hiking and biking trails connecting Millerton to the neighboring hamlets of Amenia and Wassaic. Just outside of town, the Watershed Center, a "retreat for changemakers," runs year-round retreats and workshops aimed at training activists for ecological and social justice. Set up home base there, or to concentrate more fully on Millerton exploration, at the 11-room The Millerton Inn, which opened in 2017.

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Shrine in Karma Triyana Dharmachakra Tibetan Buddhist Monastery, Woodstock, New York, USA
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While the tourist-clogged streets can make '60s countercultural reference point Woodstock feel clichéd or kitschy at times, rest assured that the "peace, love, and music" ethos of this storied town is 100 percent authentic. Namesake to the legendary 1969 music festival (which actually took place some 60 miles away in Bethel), laid-back Woodstock's artsy roots stretch back much further still—the Byrdcliffe Arts Colony, for instance, which is still up-and-running and open to public tours, was established in 1902.

This longstanding bohemian vibe permeates all facets of the town still today, with colorful spiritual, indie, and head shops (don't miss The Golden Notebook bookstore) lining Woodstock's main commercial stretch along Tinker Street and offshooting the village green—there are plenty of tie-dye and peace signs to go around. Music and cultural centers put on a robust calendar of year-round programming. Check out lineups at the Bearsville Theater, Woodstock Playhouse, Center for Photography at Woodstock, the Colony, and the Midnight Rambles at Levon Helm Studios. You won't go hungry here, either, with popular eateries like the Garden Café, Bread Alone, Oriole 9, Cucina, or Shindig, nor thirsty, for that matter, with relative newcomers like Station Bar & Curio, A&P Bar, or Reynolds & Reynolds Tap Room.

Part of the town's inspiration is rightfully drawn from its location in the heart of the Catskill Mountains; accordingly, outdoor pursuits reign supreme, with popular trails like the one leading to Overlook Mountain (don't miss a peek at the Karma Triyana Dharmachakra Tibetan Buddhist monastery, set just across from the trailhead). Nab a room at the roadside motel-styled boutique Hotel Dylan, with its fitting tagline: "Peace. Love. Stay."