There’s plenty to love about City Winery Hudson Valley — the award-winning wine, innovative food and headliner events making this a destination for locals and travelers alike — but there’s so much more to discover. Here are five ways to get the most out of your next visit.
1. It pays to be a member of their Vinofile VIP Plus wine club.
If you find yourself at City Winery at least once a month, it pays to be part of their Vinofile VIP Plus club. For $360 per year, members have access to their monthly wine pick-up party featuring a complimentary wine of the month bottle and the chance to mingle with other members over an educational event (e.g.; May is Rosé All Day where members learn how to make rosé cocktails), plus monthly wine flights, 20% off retail wine, invites to members-only events and limited edition wines, a free annual private winery tour, and no ticketing fees on ticketed purchases.
2. Their award-winning wines are Hudson Valley approved.
The Hudson Valley has no shortage of wines, but City Winery is confidently going for the gold. In the past year, City Winery took home five awards from the 2025 Hudson Valley Wine & Spirits Competition, including Double Gold for ’23 Gewurztraminer, Gold for ’23 Vin de Glaciere, Silver for ’23 Montgomery Mills and Lake Effect Merlot, and Bronze for Lake Effect Cabernet Franc.
3. They do more than incredible weddings.
It’s no secret that City Winery Hudson Valley practically owns the wedding circuit thanks to its incredible backdrop, but the property is an under-the-radar venue for private events of all sizes. Their array of indoor and outdoor spaces brings unique character for occasions of all sizes — birthdays, showers, corporate happy hours and conferences, anniversary parties, and more. One of their coolest and most coveted is the Boiler Bar, a 50-seat private space featuring the original boiler of the Montgomery Mills factory.
4. Their 2026 programming is going to be off the charts.
Music obviously plays a huge role at City Winery Hudson Valley (after all, founder Michael Dorf was the force behind New York City’s iconic Knitting Factory) and 2026 is on track for another major year. Along with local programming and outdoor music in the summer, the winery is set to proudly welcome national headliners Lyle Lovett (June 26-27), Billy Bragg (June 30), and Junior Brown (June 18) throughout the summer. Don’t miss their second annual Bud Break Spring Wine Festival (May 23) where guests can try eight new wines and paired bites on the open patio, enjoy live music and lawn games, and tack on a winery tour or library tasting of exclusive wines in the cellar. This fall, City Winery’s Crush Camp will also make a return, providing a unique opportunity to learn firsthand and be part of the fall harvest grape crushing.
5. The property is packed with Easter eggs for history nerds.
Got a history buff in your crew? Sign up for a winery tour on your next visit to soak up rare knowledge about Hudson Valley relics. City Winery faithfully maintained many of the original fixtures from the original Montgomery Worsted Mills, earning its place on the National Register of Historic Places. On the tour, you’ll spot plenty of pieces repurposed to add character such as the yarn spooler doubling as the front host stand, a still functioning 600-pound in-ground Toledo scale in the Barrel Room of the restaurant dating back to the 1920s, an original boiler situated in the Boiler Bar, and factory machinery from Westfield, Massachusetts.
Header photo: Nathan Zucker
