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

Food & Drink Outdoors & Nature Sports & Fitness Community & Causes

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Next up Sep 19

Unwind & Uncork Yoga

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Food & Drink Outdoors & Nature Sports & Fitness Community & Causes

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September 2026

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From publicly posted calendar Checked 11 hours ago

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…