Penn Oaks Winery

Discover Penn Oaks Winery's family-owned vineyards, handcrafted wines, and inviting tasting experiences. Visit us to enjoy sustainable, locally-produced wines.

Cooksville, MD

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Next up Nov 7

Unwind & Uncork Yoga

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October 2026

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Holiday Market

Sat, Nov 21, 2026 • 12:00 PM—5:00 PM · Penn Oaks Winery · Cooksville, MD

Holiday Market at Penn Oaks Winery Get into the holiday spirit at Penn Oaks Winery’s Holiday Market! Enjoy a festive day of local vendors, sipping wine, and…

Holiday Market

Sat, Dec 12, 2026 • 12:00 PM—5:00 PM · Penn Oaks Winery · Cooksville, MD

Holiday Market at Penn Oaks Winery Get into the holiday spirit at Penn Oaks Winery’s Holiday Market! Enjoy a festive day of local vendors, sipping wine, and…