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A Massive Winery Comes to This Historic Orange County Property

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City Winery’s expansion plan for Montgomery Mills includes a wine-making facility, hotel, restaurant, and more.

It’s wine o’ clock in Orange County.

As if the Hudson Valley wasn’t already a paradise for vino aficionados, the region is poised to become even more of a wine destination in the second half of 2020. That’s because City Winery, the multi-metropolis wine chain that fuses the best of the small-town wine scene with contemporary music and art, is officially open for business in Montgomery.

Making its home at the historic Montgomery Mills property located at 23 Factory Street, the winery is the first non-urban site for City Winery, which currently operates locations in New York City, Atlanta, Boston, Chicago, Nashville, Philadelphia, and Washington D.C. Helmed by Michael Dorf, the founder of New York City’s popular Knitting Factory nightclub, the chain is a favorite for wine lovers who crave the experience of a traditional winery in the heart of a big city.

“I had been looking for a while for a Hudson Valley site,” Dorf reveals. The search took over two years and considered more than 10 different locations. Ultimately, Dorf fell for the Montgomery site because it combined history with ample space for events and winemaking, not to mention easy access to New York City and Woodstock.

Of course, there’s also the sentimental tie to Dorf’s days at the Knitting Factory.

“When we discovered an old mill on ‘Factory’ Street and, next to the street sign, a sign for ‘Montgomery Mills, Knitting Wear,’ and thus a true ‘Knitting Factory,’ I knew it was destiny before even seeing the beautiful old buildings,” he recalls.

Unlike the metropolitan branches of City Winery, the Hudson Valley offshoot is more of an experience-driven location, heightening the wine and entertainment fusion that powers the winery chain at its core.

“Twenty-two acres along a beautiful river with a waterfall that we are generating electricity with hydropower is very different from our other locations,” Dorf says. “Within that will be eight acres of planted vines where we are going to grow grapes and include in the 500 tons of grapes we bring from California, Oregon, and Washington as part of our program.”

Open since June 18, City Winery welcomes the public to the former longtime industrial space in its new incarnation: a one-stop shop for wine aficionados. Fifteen wines are available by the glass via the winery’s custom, eco-conscious tap system, developed by Chief Winemaker David Lecomte. At the Barrel Room restaurant, multi-level outdoor patios overlook the Wallkill River. The dinner menu features salads, local cheeses and charcuterie, and a variety of shared plates (mushroom-goat-cheese risotto balls and duck tostadas), large plates (ancho chili-dusted salmon and cauliflower steak), and flatbreads. Sunday brunch is also served. For more information about the winery’s COVID-19 safety protocol, visit the website.

Although the winery originally planned to open in April, it used the delay caused by the coronavirus to put the finishing touches on landscaping and make sure that everything is picture-perfect.

“While openings are always challenging, this one was unprecedented,” Dorf admits. “We had over 20 confirmed weddings booked before COVID hit just based on tours in our construction site, we were just about to hire a staff of about 45 people in March, and then boom. The property is so beautiful [and] we really want to start showing it off.”

Onsite, the mixed-use development includes a restaurant, tasting room, and venue for weddings and events. Thanks to its convenient location and scenic panorama, the winery already has a number of wedding bookings for 2020 and 2021.

“City Winery is very popular for wine, shared food, and music,” notes General Manager Donna Caldwell. “It will be a very comfortable atmosphere.”

Inside The Barrel Room & Tasting Bar, City Winery’s onsite eatery, visitors can order wine on tap or from a curated wine list. According to Chief Winemaker David Lecomte, the tap selections include two to three whites, one to two rosés, and five to six reds. The menu features four or five reserve wines, which boast more aromatic complexity and robust flavor. As far as production goes, the Hudson Valley location completed its first crush in October 2019 using grapes transported by team reefer trucks from California, Oregon, and Washington. Looking ahead, it plans to generate enough vino to supply other City Winery locations across the United States.

To pair with the vino, City Winery serves everything from salads and soups to flatbreads and shared plates. Between the restaurant and tasting room and the multi-level outdoor patios, which boast views of the property and the Wallkill River, the winery can accommodate approximately 140 people. Nearby, the gallery space hosts 50, making it an ideal location for a seated dinner party or reception.

Through double doors from the restaurant and tasting room, the main event space opens to 6,800 square feet. Available not just for weddings, it also works well for large conferences and, eventually, concerts. It’s located near the gallery, which treats guests to views of the fermentation tanks on the grounds. With each of the settings at City Winery, couples and party planners can opt to use the spaces individually or combine them for large-scale celebrations. Wherever they go, they’ll be greeted by magnificent panoramas of the Hudson Valley landscape that surrounds them.

In every corner of City Winery, historic details from the property’s industrial past live on for guests.

“We haven’t thrown one thing out,” Caldwell enthuses. She and her development team incorporate bits like widgets and old-timey paperwork throughout the grounds, adapting them into everything works of art to, in the case of one yarn machine, a reception desk. On the walls, they’re hanging framed photos made with wood planks from the mill’s frames. Every piece of wood has been relumbered, and some vintage bits have even been shipped to the City Winery in New York City for reuse.

In addition to dining and drinking, City Winery hopes to become a one-stop venue for musical performances in the Hudson Valley. Like with its other locations throughout the country, it looks forward to welcoming live music to both its indoor main stage and outdoor amphitheater. Later in the year, it will unveil its bridal barn, a 1920s barn converted to a bridal loft with two guest room apartments on the bottom floor. In 2021, it will finalize the all-in-one experience with a 13-room conference center and hotel.

“Given the growth of the craft beverage industry, this is the perfect time to transform a unique industrial space to a manufacturing and event center,” says Amanda Dana, the director of Orange County Tourism. “We want to thank Michael Dorf and his team for choosing the Village of Montgomery and Orange County as the home of their newest location and congratulate them on their well-deserved Empire State Development award.”

To assist with building costs, Dorf and City Winery received $832,000 in funding through the Regional Economic Development Council. In total, the winery development in Orange County runs an estimated $5 million.

Prior to its ownership by City Winery, the historic Montgomery Mills site served as an industrial center in Orange County for over two centuries. After beginning in 1813 as the Montgomery Worsted Mills grist mill, the formerly wooden space had to be rebuilt with bricks after a fire in 1892.

Since then, the property, which was owned by brothers Jeffrey and Joseph Steinberger of Steinberger Bros Realty LLC., has been home to everything from Henry’s Attic, a hand-knitting yarn company, to H.C. Davis Boiler Co. and Valley Cabinets. Keeping with tradition, City Winery hopes to use electricity from the mill generators, along with solar power, to fuel the space.


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