Christopher Jacobs Winery at Pennings Vineyards (Seasonally Open May-Dec 15th)
Welcome to the delightful Christopher Jacobs Winery at Pennings Vineyards, where the charm of the Hudson Valley meets the art of winemaking! Situated at 320 Crawford St in Pine Bush, NY, our winery is a seasonal treasure, open from May through October. Immerse yourself in the serene landscape as you explore our vineyard, which produces a remarkable selection of high-quality wines. Our warm and welcoming atmosphere makes Christopher Jacobs Winery the perfect spot for tasting events, special gatherings, or a peaceful day out with your loved ones. Join us for wine tastings that celebrate local flavors and the unique terroir of our region. Whether you’re a wine enthusiast or a curious newcomer, our passionate team is eager to share their love for wine and the stories behind each bottle. Come experience the magic of Pennings Vineyards and make lasting memories at Christopher Jacobs Winery, where every sip tells a story!
Outdoor seating, picnic area & Indoor (soon for 2025) tasting room with vineyard views!
Seasonal: check website for drinks/events/food/music/hours/& more!
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Google Reviews
Dulcia CaroChristopher Jacobs Winery at Pennings Vineyards has become one of our favorite summer traditions. We visit several times every season with friends and family, and it’s always an amazing experience. The views are absolutely beautiful, especially at sunset. They often have live music, creating the perfect atmosphere to relax with a glass of wine, one of their delicious cocktails, or even a local craft beer if wine isn’t your thing. During the summer, they also feature food trucks—including PBF, one of our favorite local restaurants from Montgomery—and an ice cream truck that our daughter always looks forward to. What really makes this place special is that it’s truly family-friendly. There are lawn games for the kids, and our daughter always has a great time meeting new friends while we relax and enjoy the scenery. Whether you’re looking for a date night, a family outing, or a place to gather with friends, this winery offers a welcoming atmosphere, gorgeous Hudson Valley views, and a memorable experience every time. We always look forward to coming back!
Jul 18, 2026 · Google Review
Gray squirrel tree serviceNice place ,had the bowlocker pig roast today. ☺️
Jun 1, 2026 · Google Review
Johnny MoranGreat staff great drinks. Small diamond in the woods.
May 17, 2026 · Google Review
AJSimply the best
May 16, 2026 · Google Review
Patricia ZoldakI had my daughters bridal shower last week at Christopher Jacobs Winery. Monica was amazing, she not only made the place look so beautiful and welcoming, she texted me the night before to make sure the setup was to my liking. It was the perfect place for the shower and I am so pleased at how smoothly the day went. These guys went above and beyond to make sure we had the best day!! I highly recommend having any event here, they really care about making sure you have the best day.
May 1, 2026 · Google Review
Melissa LoriaThis place is stunning! The wines are amazing and the owners make the entire experience! Yall this is a MUST do! Cant wait to go back!
Nov 25, 2025 · Google Review
Alex LangeOutstanding!! Very good wine, good beer and the nicest people you will ever meet. The beautiful scenery makes this a perfect place to visit! It was well worth the 4 hour drive from southern PA!
Nov 25, 2025 · Google Review
Natalie GThis winery is owned by a hard working family. They are growing their business with a new indoor tasting room/event space. They offer a variety of their wine and other local spirits. Some small plate offerings for munching. #supportlocal
Nov 22, 2025 · Google Review
S MoAn amazing Winery with fantastic wines made by the wonderful host Monica and her husband Chris. You're welcomed into a nice outdoor bar for tasting of wines, ciders and now some local beers. Picnic tables overlooking the property or walk down a few steps to a green area with tents to enjoy your selections is a really nice touch especially if the horses are out grazing. Weekends in Summer are filled with activities like live music and food trucks. We absolutely love the Ole Wine but unfortunately is was sold out for the season. Very excited that there's going to be an inside bar with additional seating. We really love this Winery and it's always an exhale moment when we road trip up the Hudson.
Sep 22, 2025 · Google Review