Port of Leonardtown Winery

Port of Leonardtown Winery Port of Leonardtown Winery is Southern Maryland’s award-winning winery serving local wines from local vines.
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Welcome to the Port of Leonardtown Winery — Southern Maryland's award winning winery, serving local wines made from local vines! The winery is owned by the Southern Maryland Wine Growers Cooperative, a group of 12 vineyards located throughout the Southern Maryland area. The SMWG Cooperative is one of the few agricultural cooperatives in the country that has its own winery with a goal of encouragin

g wine growing in the region and making the very best wine in Maryland. The winery opened in May 2010 and has enjoyed continued success since then with over 150 awards from multiple international, national, and state competitions. Experience the flavors of the beautiful Potomac and Chesapeake Bay region -- all of our wines are made exclusively with Maryland grapes. Located in a repurposed historic commercial building within the boundaries of the Port of Leonardtown Public Park, our winery and tasting room is a relaxing, beautiful spot to enjoy local wines, music, and community. When you’ve found your new favorite local wine, pick up a bottle in our wine store, or ask us about our wine club to discover even more of what Port of Leonardtown Winery has to offer!

Sip, relax, and enjoy the weekend with us! 🍷🎶Cool off on our covered patio with fans, try our wine slushies, sangria, an...
06/10/2026

Sip, relax, and enjoy the weekend with us! 🍷🎶
Cool off on our covered patio with fans, try our wine slushies, sangria, and wine flights, and enjoy expanded outdoor seating with umbrellas. Live music and a food truck every Saturday and Sunday. Family friendly—bring everyone!

Looking for weekend plans? Come visit us! Enjoy live music daily and a local food truck. Try our wine slushies and sangr...
06/06/2026

Looking for weekend plans? Come visit us! Enjoy live music daily and a local food truck. Try our wine slushies and sangria. Bring the kids, too!

🎵 LIVE MUSIC TONIGHT 🎵Justin Crenshaw is playing live for 1st Friday! Bring your friends, grab a glass of wine, and enjo...
06/05/2026

🎵 LIVE MUSIC TONIGHT 🎵Justin Crenshaw is playing live for 1st Friday! Bring your friends, grab a glass of wine, and enjoy a perfect evening of music and great food.

06/05/2026

Our sunny patio is calling this weekend! 🥂🌞🍾 We open at noon and have live music Friday, Saturday, and Sunday with great wine, cold sangrias/slushies, and food trucks too.

☀️🍷 June Music Lineup – Welcome Summer at Port of Leonardtown Winery! 🎶Summer is here, and we’re ready to celebrate with...
05/31/2026

☀️🍷 June Music Lineup – Welcome Summer at Port of Leonardtown Winery! 🎶

Summer is here, and we’re ready to celebrate with an incredible month of live music! Join us throughout June for talented local musicians, award-winning wines, refreshing wine slushies, sangria, and a relaxing atmosphere perfect for gathering with friends and family.

Whether you’re looking to unwind on the weekend, enjoy great food and music, or simply sip your favorite wine while soaking up the summer vibes, Port of Leonardtown Winery is the place to be.

🎵 Live Music Throughout the Month
🍷 Award-Winning Wines
❄️ Refreshing Wine Slushies & Sangria
👨‍👩‍👧‍👦 Family-Friendly Environment
🌳 Beautiful Outdoor Setting

Bring your friends, bring your family, and make Port of Leonardtown Winery part of your summer tradition. We can’t wait to welcome you for a month filled with great music, great wine, and great memories!

Cheers to Summer! ☀️🍷🎶

🍷 Sunday at Port of Leonardtown Winery – May 31 🍷Join us for another beautiful day at the winery this Sunday, May 31!🎶 L...
05/31/2026

🍷 Sunday at Port of Leonardtown Winery – May 31 🍷

Join us for another beautiful day at the winery this Sunday, May 31!

🎶 Live Music: Billy Breslin & The Swamp Weasels starting at 2:00 PM
🌮 Food Truck: Heidi’s Eats & Sage’s Treats
🍷 Award-winning wines, wine flights, slushies, and sangria available

Slushie Flavors:
🫐 Blueberry Lemonade
🍍 Pineapple Passion

Sangria Flavors:
🍉 Watermelon Rosé
🍓 Very Berry

👨‍👩‍👧‍👦 Family-friendly atmosphere
🕛 Tasting Room Hours: 12:00 PM – 6:00 PM

Gather your friends and family, relax with a glass of wine, enjoy great food, and spend the afternoon listening to live music at Port of Leonardtown Winery! 🍷🎶☀️

Join Us Today! 🍷🎶Spend your Saturday with us at Port of Leonardtown Winery!Enjoy live music by David Sparrow and delicio...
05/30/2026

Join Us Today! 🍷🎶

Spend your Saturday with us at Port of Leonardtown Winery!

Enjoy live music by David Sparrow and delicious food from Jamaican Grill while you relax with award-winning wines, wine flights, sangria, and our refreshing wine slushies.

Today’s Slushie Flavors:
🍋 Blueberry Lemonade Pineapple Passion Sangria
🍉 Watermelon Rosé
🫐 Very Berry

📍 Family-Friendly
⏰ Tasting Room Hours: 12 PM – 6 PM
🎵 Live Music Starts at 2 PM

Gather your friends and family and join us for a perfect afternoon of wine, music, and great food. We look forward to seeing you! 🍷☀️

Join us on another great weather day, Friday May 29. Cousins Maine Lobster will be with us for the day 12-8pm. We have...
05/29/2026

Join us on another great weather day, Friday May 29. Cousins Maine Lobster will be with us for the day 12-8pm. We have added live music, Better w/ Whiskey. All proceeds for music go to our local Camp Dare program in St. Mary’s. Come out, support, enjoy our Award Winning wine, lobster and great music. SPECIAL HOURS TIL 8pm, music starts at 4:30pm.

Don’t let the weather ruin your weekend plans. Join us for a SUNDAY afternoon of good wine, music and eats. Family fri...
05/23/2026

Don’t let the weather ruin your weekend plans. Join us for a SUNDAY afternoon of good wine, music and eats. Family friendly, covered tent are as well as outdoor tables. Wine slushie flavors of Blueberry lemonade & Pineapple passion. Sangria flavors are watermelon rose & very berry. Non- alcoholic ones too.

We're hiring! 🍷🍇 We are seeking a cellar assistant to help with all things wine production, from grape to bottle. This p...
05/23/2026

We're hiring! 🍷🍇 We are seeking a cellar assistant to help with all things wine production, from grape to bottle. This position is part-time (weekdays are flexible), with full-time hours through harvest Sept-Nov. An ideal candidate is someone who has a flexible schedule, loves physical work, doesn't mind getting dirty, and is comfortable working with production equipment.

For more details, follow the link below or send resume to [email protected]🍷

https://www.indeed.com/job/cellar-assistant-e18a300a1b7753fd

Address

23190 Newtowne Neck Road
Leonardtown, MD
20650

Opening Hours

Monday 12pm - 6pm
Tuesday 12pm - 6pm
Wednesday 12pm - 6pm
Thursday 12pm - 6pm
Friday 12pm - 6pm
Saturday 12pm - 6pm
Sunday 12pm - 6pm

Telephone

+13016902192

Website

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