City Winery Is Vino Paradise on a Historic Orange County Property

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

City Winery. Photos by Adam Pass, courtesy of City Winery

The Hudson Valley winery at Montgomery Mills includes a wine-making facility, hotel, restaurant, and more, with concerts and events to boot.

By Sabrina Sucato and Raphael Beretta

It’s wine o’ clock in Orange County.

As if the Hudson Valley wasn’t already a paradise for vino aficionados, the region has become even more of a wine destination. 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.

- Advertisement -

City Winery Sunset

“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.

Southside Johnny

- Partner Content -

As far as events go, locals should keep an eye out for the “Concerts in the Vineyard” series. City Winery Hudson Valley hosts iconic acts like Southside Johnny and the Asbury Jukes, Joan Osborne, Amy Helm, and more at an expansive outdoor amphitheater. In addition to dining and drinking, City Winery hopes to become a one-stop venue for musical performances in the Hudson Valley. Its engaging, intimate concert series also features tribute acts covering artists like Elton John, Amy Winehouse, and Tom Petty. Visit their website for a full list of upcoming shows through October.

At the Orange County winery, guests can savor breathtaking panoramic views and gorgeous sunsets set to music all summer long. Tickets are available for purchase online for seats along the grand lawn or in the VIP section. The grand lawn has plenty of room for ticket holders to spread out and enjoy each performance as well.

City Winery Amphitheater Concert

Plus, City Winery Hudson Valley takes its delicious culinary program outside, giving visitors dinner and a show. The Montgomery destination’s two spacious patios create a wonderful atmosphere during the evenings with mood-setting string lights, cozy heat lamps, and outdoor fireplaces. Al fresco diners overlook the majestic Wallkill River and the historic property as they sample a wide range of foods drawing inspiration from the top wine-producing regions in the world, including Italian, French, Spanish, and Middle Eastern cuisine. On the menu, guests can find refreshing poke bowls, locally sourced cheese and charcuterie plates, and savory duck tostadas, just to name a few choices.

City Winery also unveiled its bridal barn, a 1920s barn converted to a bridal loft with two guest apartments on the bottom floor. Gorgeous vineyard and waterfall packages set the scene for romantic rehearsal dinners, engagement brunches, private events, and bridal showers. A vast range of ceremony and reception choices creates unforgettable wedding memories. Mini staycations await at The Barn, which features three rustic rooms. Interested individuals can reserve stays by emailing

- Advertisement -
City Winery Hudson Valley Bridal Barn
City Winery Hudson Valley Bridal Barn | Photo by Alicia King

“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 2020, 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. Although the winery originally planned to open in April 2020, 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 2020, and then boom. The property is so beautiful [and] we really want to start showing it off.”

City Winery Hudson Valley

Onsite, the mixed-use, fully functioning development includes a restaurant, tasting room, and venue for weddings and events. Smaller events like wine pairing tutorials, themed tastings, cocktail workshops, and more celebrate the seasons in unique fashion.

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 five to six whites, one to two rosés, and seven to eight reds. The menu features several 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.

Through double doors from the restaurant and tasting room, the main event space opens to 6,800 square feet. 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 are 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.

The 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.

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.


“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.”

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.

Related: A Massive, Abandoned Zoo Is Reborn in Catskill

Our Digital Partners

Learn how to become a digital partner ...

Our Excellence in Nursing Awards take place on May 1!

Our Best of Hudson Valley ballot is open through March 31!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.