Catskill street scene. Credit: John Garay

The debate about just where in the Hudson Valley “Upstate” actually begins may never be resolved to everyone’s satisfaction, but most would agree: When you reach the Rip Van Winkle Bridge, the span that connects Columbia and Greene counties, you’re well on your way.

Nor are you in the hinterlands. The county seatsโ€”Hudson in Columbia and Catskill in Greeneโ€”have gained critical cultural mass, becoming deservedly popular destinations for a day trip, a weekend, or a reinvented life.

Hudson came first. Having an Amtrak station meant that adventurous wanderers from New York City could hop right off the train and discover a walkable little city with gorgeous curves, the 18th-century creation of Quaker whalers from New England who wanted an inland port. The city took off: in 1791 it hosted Thomas Jefferson and James Madison, there to convince a prominent distiller that rum could be made just as well from French wine as from the West Indian molasses peddled by the Brits.

Victoria, 1991โ€“2000, by Philip Grausman at The Fields Sculpture Park at OMI International Arts Center in Ghent. Credit: John Garay

The railroad blocked the harbor in 1850; by the 1900s, the city had reinvented itself as an industrial center. By the 1990s, heavy industry was shuttered and Hudson was re-reinventing itself as an antiquing and arts destination.

Modern-day Hudson is one chic little burg. “My favorite new thing in Hudson,” says Layla Kalin, “is definitely Lil’ Deb’s Oasis. That restaurant is bomb on so many levelsโ€”the food is amazingly adventurous and bright, the staff is to die for, the interior is fun and cozy, the vibe is forward thinking and radically inclusive. Dinner there is always popping, and as a mom I don’t make it out often. But since they started serving lunch, I can pop in for some sustenance and happiness regularly now!”

Tomm Roeschlein, Shanekia McIntosh, Sara Beckley, Rebecca Becker, and Enky Bayar in front of The Spotty Dog Books and Ale in Hudson. Credit: John Garay

Kalin is the owner of Kasuri, a boutique offering “cutting-edge directional fashion” from Japanese, European, and American designers. “I started hanging out in Hudson around 2009, was upstate full time in 2012, started working on Kasuri in 2013 and opened in 2014,” she says. “In some ways I feel like a newbie, but I’ve also seen Hudson develop and grow a lot. It’s such a cool little town, so cool people are drawn to it to continue working on their cool projects or even just visit. I like that Hudson has this metropolitan mindset in this little gem of a river town.”

The “little gem of a river town” with its wealth of classic architecture is packed with food, drink, lodging, retail and culture of all sorts these days. Visitors can choose among a plethora of bed-and-breakfasts, inns, and hostelries like the Rivertown Lodge, with an on-premises tavern serving locavore food and curated craft cocktails. They can venture out along Warren Street (tagline: “Upstate’s Downtown”) to shop top-notch retail, finding creative places like Spotty Dog Books and Ale, a historic firehouse done over and filled with books, art supplies, gifts, toys and hand-crafted ales on tap. They can dine on Malaysian-inspired cuisine courtesy of Zak Pelaccio at Back Bar, housed in the back of an antique shop that was once a gas station.

Jamie at John Doe Books and Records in Hudson. Credit: John Garay

This is upstate headquarters for giant Internet makerspace Etsy. And just last month, Hudson-lovers learned they’d won the $10-million prize in Governor Cuomo’s Downtown Revitalization Initiative sweepstakes. Current plans for the money include mixed-use development, waterfront improvements, and workforce development designed to make sure the rising tide lifts all boats, something Hudson’s intelligentsia recognize as a key point. “We can’t afford to lose affordable housing,” says Colin Stair, proprietor of the distinguished Stair Galleries auction house. “If everything just keeps getting more expensive and people are priced out, then where will all the cool people go?”

Don’t miss Chatham, a lively and vibrant village half an hour north. Chatham Brewing took the 2017 Matthew Vassar Cup in 2017, and the town has not one but two theaters: the Mac-Haydn produces professional musicals in a theater-in-the-round setting, and the Crandell, home base for the Chatham Film Club, will hold the eighteenth annual FilmColumbia Festival next month (October 22-29). There are some very cool bars to relax in after browsing nifty retail like Pookstyle, nicely described by RuralIntelligence.com as “a museum store without a museum,” and the country designs at Crow Cottage. Chatham is where you can get alterations done, brass instruments repaired, and fine art restored.

Matt Jones and Lea Carey in Hudson Credit: John Garay

In between these two outposts, in Ghent, is Omi International Arts Center. Stop in for Sunday Music on the Patio (this month it’s soundBarn) or the Light Into Night event on September 16, billed as “an evening of art and surprise” mingled with dinner and dancing. Ghent is also where you’ll find the deep-green Hawthorne Valley Farm Store with its biodynamically grown yummies.

Across the Rip Van Winkle, the village of Catskill’s star has been rising. Lumberyard Contemporary Performing Arts, birthed from the American Dance Institute, has just partnered up with the Brooklyn Academy of Music to allow artists to premiere new works, building on their mission as an incubator. They’re also renovating and building fine new facilities with the help of five million dollars in social investment funding from the Rudolf Steiner Foundation, the largest amount RSF has ever given and the first grant to a performance art institution. Construction is slated to begin in November. “It’s not just about the artists but about the community,” says executive and artistic director Adrienne Willis. “To have audiences from the Catskills and Berkshires be the first eyes on a piece is incredibly valuable to both the artists and the community here. People come with no preconceived notions, open heart and mind, and we try to break down barriersโ€”our audience educator presents in the lobby before the performance, and we have receptions after so the artist can get sincere feedback. I think the benefits will spill over to the smaller arts organizations and to all of Greene County.” Lumberyard will host its second annual Shindig on September 23, blending new work from Urban Bush Women with bluegrass, Rip Van Winkle Brewery beer, and barbecue from American Glory.

Catskill’s Bridge Street Theatre is producing the award-winning play “How To Pray” in its reclaimed factory space this month (September 14-24). Joe’s Garage, an actual renovated garage, hosts art openings and events. HiLo Catskill blends cafe, bar, gallery, and performance space.

John Sowle and Steven Patterson at Bridge Street Theater in Catskill. Credit: John Garay

“We have a lot of new creative businesses lately,” says Liz Kirkhus, membership director for the Greene County Chamber of Commerce. “There’s the Rodney Shop, where Rodney Greenblatt has his paintings and ceramics and sculpture. The Village Common has natural three-ingredient candles, and the Corduroy Shop makes all kinds of things out of reclaimed vintage fabrics and does upholstery. CounterEv makes furniture out of reclaimed bowling alley wood. The Thomas Cole House has a really cool interactive exhibit right nowโ€”about 25,000 people a year blow through there.” Catskill is also where you’ll find Magpie Bookshop, “specializing in awesome” both new and gently used.

For dinner, how about wandering to nearby Athens? It’s another great little river town building its very own brand of cool. You can dine on elegant French cuisine at Rive Gauche Bistro, or eat down on the waterfront at Hagar’s Harbor, where the signature burger blends Angus beef with brisket. Athens is also the home of Crossroads Breweryโ€”one stop on the Catskill Beverage Trail which will be hosting its very first festival at Windham this November. And Bonfiglio and Bread Bakery, formerly of Hudson, is reopening in Athens soon.

Greene County’s ski mountains aren’t just for winter anymore. Hunter Mountain‘s festival offerings are legendaryโ€”their Oktoberfest begins in late September, and your day can include a zipline zoom or a skyride to the summit. Windham Mountain is huge on the mountain biking circuit and has created a new trail, the Kaaterskill Cruise, just for newbies to the sport. Windham also offers a resort golf course and a skyride of its own, and presents live music at the Wheelhouse Lodge.

Laura Davidson and Liam Singer at Hi-Lo Cafe Bar in Catskill. Credit: John Garay

Don’t miss a stop in quirky Tannersville, called the Painted Village in the Sky for its brightly colored building facades on Main Street. Maggie’s Krooked Cafe is one of several nice places to grab a bit; Slam Allen will be doing Music In The Park on September 8, and on September 24 it’s time for the fifth annual Cruisin’ On The Mountaintop car show.

In Coxsackie you’ll find the Reed Street Bottle Shop, dedicated to the belief that wine should be fun, and the classic Hi-Way Drive In Theatre. Coxsackie is also home to Mansion and Reed, a general store packed with local artisanal goodies with a B and B up top. “These two sisters own the whole block there, and they’ve just opened a card shop. The bottle shop has been hosting tastings and events. And Coxsackie has a lovely farmers’ market on Wednesdays,” says Kirkhus. “I think anyone who hasn’t wandered around Greene County in a while is missing out.”

So venture out past the end of the suburbs. Plan a leaf peeping trip and discover why this area sparked the Hudson River School of painting. Take the Rip Van Winkle Bridge, and discover communities that are wide awakeโ€”and ready for countless flavors of fun.

Michelle Williams and Stephanie Dougherty at 394 Main in Catskill. Credit: John Garay

Anne's been writing a wide variety of Chronogram stories for over two decades. A Hudson Valley native, she takes enormous joy in helping to craft this first draft of the region's cultural history and communicating...

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