Port of Leonardtown Winery - Leonardtown, MD

Port of Leonardtown Winery - Leonardtown, MD Port of Leonardtown Winery - Leonardtown, MD Port of Leonardtown Winery - Leonardtown, MD Port of Leonardtown Winery - Leonardtown, MD Port of Leonardtown Winery - Leonardtown, MD
Shade Available
Covered Shelter
Seating
Parking

Port of Leonardtown Winery – Dog-Friendly Fun in Leonardtown, Maryland

Located in the heart of Leonardtown, Maryland, Port of Leonardtown Winery offers a unique combination of a dog-friendly atmosphere and local charm. Enjoy a variety of locally produced wines, slushies, and sangria in a laid-back, scenic outdoor setting that’s perfect for spending an afternoon with your canine companion. The winery is well-loved by the community for its welcoming vibe, quality wines, and commitment to providing a great experience for all visitors—even the four-legged ones!

Dog owners appreciate the spacious, grassy outdoor area where leashed pets are welcome. The grounds provide an enjoyable atmosphere for pet owners to relax, socialize, and let their dogs enjoy the fresh air. Whether you’re stopping in for a tasting, enjoying live music, or just seeking a dog-friendly hangout in Leonardtown, this winery stands out as a local favorite for dog owners seeking pet-friendly trails and outdoor activities in St. Mary’s County.

Frequently Asked Questions

  • Are dogs allowed at Port of Leonardtown Winery? Yes, dogs are welcome in the outdoor areas, provided they are on a leash.
  • Is there shade or shelter available? Yes, there are shaded and covered areas outside where guests and their pets can relax.
  • Are there benches or seating areas for owners? Yes, seating is available both inside and out, making it easy to relax with your dog.
  • Are there pet-friendly activities onsite? Yes, there are lawn games such as Jenga, and the outdoor space is perfect for socializing with your pet.
  • Can I host a dog birthday party or event here? Yes, the winery is available for private events and parties, which can include dog-friendly gatherings in the outdoor space.

Reviews

Tim Campbell

They offer a variety of locally produced wines, with quality ranging from good to very good. Nice outdoor space in a park to enjoy it. Sangria and slushies are also available. dog friendly

Lori B

We had my mother’s 85th birthday party here. From the beginning Sharon the event coordinator was so helpful and accommodating. She offered lots of ideas and made the planning part so easy. Our party was after hours so for a very reasonable fee-we had the whole place to ourselves. Sharon and Selina kept all of our guests happy and well served-especially making sure that the guest of honor was taken care of. (Did I mention that the wine and slushies are all fantastic?!) My mother smiled all night and will fondly remember this special time.
We are so lucky to have such a special place in our community. Please don’t hesitate to book an event here-you won’t be disappointed!

San Rey

I was very impressed by this little winery. Extensive selection of wines offered by the bottle, glass or flights of 3. Something for every palette. Highly recommend the Old Line Red. Can bring your own food or purchase a snack inside. Lovely place to spend an afternoon.

Dee Deigh

Stopped by with friends for wine tasting. For a Saturday it was an awesome experience. We ended up buying the Vidal Blanc and got some food from the food truck called Heidi’s Eats and Sage’s treats. Kailie who was our wine tasting expert was well cast about the every aspect of the wine we were tasting and made the experience a fun and educational one. They had live music playing and the overall atmosphere was just friendly and jazzed. I think I found a new place for my once a month wine treat. You will like this place.

Kimberly Mann

I am not a big wine drinker. My sister-in-law who lives in St. Mary’s County suggested a visit while we were in town. I wasn’t sure about it since we were traveling with our teenage sons. The boys actually enjoyed the visit and really liked the lawn Jenga. I wish I could remember his name, but the staff member who did our tasting was great. I really only like super sweet wines when I have wine. He customized the tasting especially for me. What he offered and suggested was spot on for my liking. Additionally he did two different tastings for the other 3 people in our party. Highly recommend. You could spend just a few minutes or a few hours. Of note, you are not visiting a huge vineyard, just a storefront offering tastings and an outdoor area to enjoy a glass or two of wine. The vineyards are a co-op of locally sourced grapes.

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