It is easy to see why Old Westminster Winery continues to get all the hype. I have been several times already, but this was Deke’s first visit, and he loved it. From the moment we arrived, everything felt dialed in, and the food, service, and ambiance were on point like always.
One of my favorite parts of this visit was booking one of their private cabanas. They are genuinely a dream if you want a cozy, refined setup for your group, and they make the whole experience feel extra special. They are also pet-friendly, so yes, you can bring your floofs along for the fun.
What To Order at Old Westminster Winery…
We started with drinks, and everything we tried was delicious. We ordered the Just For Fall Flight for $28, which featured their 2024 Trio, their 2024 Rosé, and their Rev 10th Edition. It was the perfect option if you want a little tasting moment and cannot decide what to commit to. I also ordered a glass of the 2024 You Are My Sunshine for $15 because I was craving something bubbly, and it totally hit the spot.
You can never go wrong with a fruity rosé in my opinion, and this one tasted like strawberries in the best way. I also tried their Tiramisu Latte for $10, and I need to talk about it because it was so good. I was worried it would be too sweet, but it was actually perfectly balanced and tasted exactly like a cozy dessert in drink form. Their artisanal coffees are made with beans from Black Acres Roasters, which made me love it even more. Deke ordered the Crème Brûlée Cortado for $7, and he was very happy with it.
For food, we started with the cheese and prosciutto board for $38, and it was such a strong start. I love that they source local whenever possible, and this board was a great example of how thoughtful their ingredients are. It came with several cheeses, marcona almonds, castelvetrano olives, fruit preserve, and wood-fired bread, and it was honestly a banger of a board.
Of course, we had to order their wood-fired pizza because that is one of the things they are known for. We got a few pies to share, and we went with the pepperoni and hot honey for $21, which is always so good and never misses. We also tried the delicata squash and prosciutto for $25, and it was such a great seasonal option that felt cozy, balanced, and perfect for fall.
If you want to pair your winery day with another fall outing nearby, Larriland Farm in Woodbine is about 12 miles away for pick-your-own apples at a Howard County orchard that’s been running for decades.
We wrapped it all up with dessert, and I was very happy about that decision. We ordered the apple cheesecake tart for $11 and the macarons, which are $6 per order and come with two. The tiramisu macarons were unreal, and I ate both of mine, which is why I am saying this with my full chest: no regrets and sorry not sorry, lol.

If you have not been yet, you really need to go. It is truly an amazing experience, and I genuinely think you will have the best time. A huge thanks to the Old Westminster Winery team for hosting us.
📍1550 Old Westminster Rd, Westminster, MD
⏰Th 5-9pm, Fr-Su 10-9pm
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