Tucked within the Hudson Valley about 90 miles north of New York City, Kingston is one of Upstate New York's most up-and-coming cities, with streams of artists pouring in, creative entrepreneurial ventures taking shape, and trendy new eateries opening up all the time. It’s an exciting wave of revitalization, fueled by the contagious enthusiasm of locals and built upon the diverse architectural bones of nearly four centuries of settlement that reveals a pocket of fascinating history for every shiny new hot spot du jour.
Wedged between the Catskill and Shawangunk Mountain ranges to the west and the Hudson River to the east, the city spans three distinct neighborhoods, including the dynamic, walkable, and historic business district of Uptown; the once-blighted industrial arts mecca in Midtown; and the maritime-flavored Downtown (aka the Rondout), on the waterfront.
Boutique Hop in Uptown Kingston
Uptown Kingston (aka the Stockade District) presents a stroll-worthy span of eclectic mom-and-pop shops, eateries, tattoo parlors, bars, yoga studios and historic sites galore.
The photogenic two main drags—North Front Street and Wall Street—are framed by old-fashioned covered arcades and brim with new and old-timey businesses. Along North Front Street, music lovers can pop in to flip through crates of vintage vinyl at Rocket Number Nine, peruse CDs and books at Rhino Records, or strum guitars at Stockade Guitars; around the corner, on Wall Street, pick up a hat to go with that new or used CD find at Blue-Byrd's Haberdashery & Music.
Another hybrid venture is town hub Outdated, a coffee and antique shop rolled into one. In the same vein, bibliophiles can pair book-browsing with caffeine or libations at Rough Draft Bar & Books (there’s also straight-up used bookstore Half Moon Books).
Foodies might dip into Bluecashew Kitchen Homestead for kitchenware and cooking classes, or stock up on locally sourced fare from Duo Pantry. Design hawks will appreciate the stylish home goods at Exit Nineteen; artists flock to Catskill Art & Office Supply; fashionistas will find inspiration at clothiers Lovefield Vintage or Hamilton & Adams; and gift-givers are sure to turn up that perfect something at quirky boutique Bop to Tottom.
Soak Up History in the Stockade District
Surely, the historic air of Uptown's Stockade National Historic District hasn’t escaped even the most intent-on-retail-therapy visitor, with its bluestone sidewalks, old stone houses, and altogether unique architectural tapestry dating back to 17th-century colonial times. Its name harkens back to the days when the Dutch settlement here was fortified by stockades to ward off skirmishes with the Esopus Indians. That small colony would rise to considerable importance: Designated as the first capital of New York in 1777, it was subsequently charred by the torch-bearing British military later that year (though many buildings were later restored by resilient colonists).
Time travel to colonial times at the Four Corners intersection (at John and Crown streets), the only crossroads in America where all four corners are occupied by buildings that predate the Revolutionary War. One of those structures is the Matthewis Persen House (dating to 1661), one of a handful of historic Kingston homes open to the public as museums. Another is the nearby Federal-style Fred J. Johnston Museum (1812), known for its American decorative arts collection and period furnishings.
For more relaxed immersion, three of the quarter's historic stone buildings have been repurposed for wining and dining. Try the above-mentioned Rough Draft Bar & Books (1774); the cozy Hoffman House Restaurant (1679); or cocktail lounge Crown (said to be situated with the city’s oldest home).
At the Georgian-style Ulster County Courthouse (1818), the New York State Constitution was drafted in the original courthouse here in 1777; it was also the site of abolitionist Sojourner Truth’s legal victory in gaining her son’s freedom from slavery.
Find Farm-Fresh Fare at the Kingston Farmers Market
Held outdoors on Saturdays from mid-May through mid-November along Uptown’s Wall Street (between John and Main streets), the Kingston Farmers Market is a way to dig in on the bounty of the surrounding Hudson Valley agricultural region, while rubbing elbows with the locals. Amidst the parade of strollers and pups, you’ll find plenty of produce, naturally, but also locally sourced meats, eggs, wine, beer, honey, baked goods, flowers, specialty and prepared foods, and more (plus live music, too!).
During the winter, the market moves indoors to the Old Dutch Church and switches to an every-other-Saturday schedule.
Wander the Waterfront at the Rondout
Fringing the Rondout Creek and the Hudson River that it feeds, Kingston’s waterfront area exudes a relaxed, maritime feel. Here in Downtown, also dubbed “the Rondout” or “the Strand,” a walkable stretch of eateries, galleries, and boutiques comes clustered along Broadway and West Strand Street. Some favorite establishments include Clove & Creek, selling the wares of local makers along with fresh coffee; flower/gift shop Hops Petunia; and the Arts Society of Kingston, featuring rotating exhibitions, workshops, and performances.
History buffs will appreciate simply wandering the designated Rondout-West Strand Historic District, as well as attractions like the Hudson River Maritime Museum, which nods to the region’s heritage via artifacts and historic vessels; the Trolley Museum of New York, showcasing vintage trolley and subway cars from around the globe (actual trolley rides are also available along the waterfront); and the Reher Center for Immigrant Culture and History, which hones in on immigrant history in the Hudson Valley.
Find a sandy stretch for a Hudson River swim at Kingston Point Beach, a pleasant riverfront stroll at Kingston Point Rotary Park, or perhaps the boats bobbing about on the Rondout Creek alongside T.R. Gallo West Strand Park are more your speed.
Indeed, from the Rondout, you can take to the waterways with narrated two-hour sightseeing cruises aboard Hudson River Cruises’ 300-passenger Rip Van Winkle; rent a kayak or canoe from A Day Away Kayak Rentals; or charter a sailboat from Tivoli Sailing Company or Hudson Sailing.
At the mouth of the Rondout Creek, the Rondout Lighthouse (1915) marks the last of three lighthouses to stand on the site and one of only seven remaining on the Hudson River. Accessible solely by boat (seasonal tours are run by the Hudson River Maritime Museum), you can also sneak a peek of the lighthouse on land, at Kingston Point Rotary Park.
Listen to Live Music
Kingston is known for its vibrant music scene. The biggest acts to pass through town make way for Midtown’s Ulster Performing Arts Center (UPAC), a 1927 show palace that’s fresh from an extensive $5.4 million renovation as of late 2017. Presented by the Poughkeepsie-based Bardavon, the 1,500-seat venue hosts plenty of concerts—past headliners have included David Byrne, Joan Jett, and the Beach Boys’ Brian Wilson—as well as theater, dance, film, and comedy events.
The city’s other major music hub for indie and up-and-coming acts is Uptown’s BSP Kingston (Backstage Studio Productions), a repurposed early 20th-century vaudeville/movie theater that’s hosted acts like Grizzly Bear, Television, Dresden Dolls, and Yo La Tengo. They occasionally present intimate shows at the ballroom of Midtown’s art deco The Beverly Lounge, too. For lower-profile local and touring bands, live music is frequently featured at low-key locals’ haunts like beer/burger spot The Anchor, microbrewery Keegan Ales, and North Front Street dives Uncle Willy's and Snapper Magee's.
Get Your Art Fix on First Saturday
The best way to put your finger on the pulse of Kingston’s vibrant arts scene is to pass through town on the first Saturday of the month, when the city’s First Saturday event sees galleries and arts venues across the city swing open their doors for public receptions rife with wine, cheese, and, of course, loads of art. On any given First Saturday, you might find some 20 participating venues, many of which fall within the Midtown Arts District. This burgeoning district contains a bevy of long-neglected industrial spaces that are being reimagined as spaces for artists to live and work.
Some regular First Saturday participants worth seeking out include Midtown’s The Lace Mill, a brilliant example of an adaptive reuse project, with 55 artist lofts and several public galleries set within a repurposed, century-old lace curtain factory, as well the Rondout’s Arts Society of Kingston, which puts on 24 shows a year in its two galleries.
Sync Up With Special Annual Events
Kingston puts on a slate of popular annual events, including its crowning glory: the arts, music, and wellness festival, O+ (pronounced "O positive"). Held each fall since 2010, it was conceptualized to provide a barter system for un- and under-insured artists and musicians to exchange their talent for donated healthcare and wellness services (a model that’s inspired spin-offs in several cities throughout New York, Massachusetts, and California).
The rest of us reap the rewards via a three-day weekend event spilling over with dozens of concerts, art installations, performing arts showcases, and wellness happenings in citywide outdoor spaces and venues, large and small. The major legacy of O+ has been the large-scale murals that are commissioned to debut with each year’s festival: To date, 36 murals have embellished buildings throughout the city.
Other cool events worth showing up for include the two-day Art Walk Kingston in September, featuring more than 100 participating artists for studio tours, gallery receptions, and cultural events across Kingston. If you happen to be around, don't miss the biennial Burning of Kingston, a citywide theatrical reenactment of the British’s 1777 Revolutionary War-era torching of Kingston, taking place in odd-numbered years.
Admire City Murals
Thanks to the O+ festival’s mural-making initiatives, Kingston has been looked at as an open-air canvas by local and visiting street artists, with 36 large-scale murals that have transformed the city’s walls and character.
The bulk of the works are clustered in Uptown (where you won’t miss the towering crowd-pleaser Artemis Emerging from the Quarry by artist Gaia) and in Midtown (home to the handiwork of noted street artist Lady Pink, with her Native Americans Discover Columbus, and Nani Chacon’s We've Always Found Our Way Home). Aesthetics vary, but works strive to reflect general themes like inclusiveness, diversity, underrepresented communities, and feminine leadership. You can use the mural map of the city to explore them on your own self-guided tour.