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The Port of Leonardtown Winery is the perfect unique space for your small wedding or reception, bridal/baby shower, birthday celebration, corporate dinner, or any other special event you are planning. 





Tasting Room Rentals 

This space is available throughout the year, before or after the Port of Leonardtown Winery’s business hours. This rental option grants you access to all rental spaces, weather permitting: the tasting room, covered patio, outdoor patio, gazebo, and production area – when the winery is not in active wine production. When all spaces are available, we can host events of 120-150 people, and arrangements can be made for tents to hold additional people outside. In the winter, we can comfortably hold parties of up to 80 people.  

Gazebo Rentals 

This space is only available for rentals April through November, during the Port of Leonardtown Winery’s business hours. Our enclosed gazebo offers a private space for food and/or gifts during your bridal shower, work lunch, family gathering, etc. The gazebo, along with the tables designated for this space, can host events up to 40 people. Arrangements can be made for tents to hold additional people outside. Rent this space over the weekend to enjoy the live entertainment we have at the winery! 

Due to our limited space and seating, all parties of 12 or more are required to rent the gazebo space when they visit the Port of Leonardtown Winery. Arrangements can be made on a case by case basis for parties of this size during the winter months when the gazebo is not available.  

Tank Room Rentals 

This space is only available when the winery is not in active wine production. Please contact the Port of Leonardtown Winery for information about pricing and availability. 

December Holiday Party Rentals 

During the holiday season, special accommodations may be made to allow large office/family parties, happy hours or other celebrations. Such accommodations can only be made on Mondays through Thursdays in December during our normal business hours (12-6 pm). These exceptions are entirely circumstantial, so please contact the Port of Leonardtown Winery for information about pricing and availability. 


Additional Notes 

Due to our licensing, we cannot allow any outside alcoholic beverages on our premises. However, we do permit all outside food to allow our guests to host potluck-style or professionally catered events. To lock in your reservation, a nonrefundable deposit of half the rental fee must be received within 10 business days of event booking, and all parts of the rental agreement must be signed by the individual planning the event. The agreed upon rental time includes setup and cleanup of your event, with a 15-minute grace period before and after your rental time. Any events that continue more than 15 minutes after the rental end time will be charged for an additional hour. 


Interested in renting our space? 

Please contact our Event Coordinator at 301-690-2192 or to schedule an appointment to view the space and go over pricing details.