Cancel

    Open app

    Search

    Penn Oaks Winery

    3.9 (14 reviews)
    Closed Closed

    Penn Oaks Winery Photos

    You might also consider

    Recommended Reviews - Penn Oaks Winery

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    a bottle of wine on a table
    Janee F.

    Loved our visit to Penn Oaks Winery for my 30th birthday! Great service and fantastic German wine.

    Wrap around deck with Adirondack chairs
    Jess C.

    Cannot express what a great day we had today at Penn Oaks. The staff is AMAZING! So down to earth, very involved and available. We were gifted with nice breezes and cooler temps to be able to sit outside on the back deck to enjoy the lovely views. The wines are pleasing to whatever range your tastes go, with maybe the exception of super dry wines, as they tend to run middle of the road as far as sweetness. Our group all found wines we really liked though, our collective favorite was the Montepulciano red. The tasting room is so pretty, the pricing is very reasonable. They are only open on sundays, so don't miss out on this fabulous find. =)

    Our cheese, crackers, & snacks to go with the tastings.
    Portia B.

    Penn Oaks is a beautiful gem of a tasting room and so close. My girlfriend and I met at Penn Oaks for Sunday lunch. We were pleasantly surprised to be able to taste all their wines for $10. The mulled Cabernet Sauvignon was absolutely amazing. Hope to see it offered in Fall 2022 to take home a batch for the holidays! I bought a bottle of their sweet Liebfraumilch and my girlfriend bought a bottle of their Cabernet Sauvignon (un-mulled). Both of us would definitely visit this family establishment again. Applause to this courageous family team of winemakers! Currently they are open on Sundays.

    Aerial Viwe of Penn Oaks Winery in Cooksville, Maryland

    See all

    10 months ago

    Helpful 1
    Thanks 1
    Love this 0
    Oh no 0
    Photo of Sara L.
    171
    444
    1351

    2 years ago

    Helpful 2
    Thanks 0
    Love this 1
    Oh no 2

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 1

    2 years ago

    Helpful 0
    Thanks 1
    Love this 0
    Oh no 0

    6 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Jess C.
    0
    68
    206

    5 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Ron C.
    1538
    1211
    688

    4 years ago

    Helpful 1
    Thanks 0
    Love this 2
    Oh no 0
    Photo of Portia B.
    25
    11
    42

    5 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Debra W.
    42
    137
    70

    7 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0

    6 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0

    Ask the Community - Penn Oaks Winery

    You might also consider

    Verify this business for free

    People searched for Wineries 5,169 times last month within 30 miles of this business.

    Verify this business

    Black Ankle Vineyards - Natural spaces for wildflowers and beneficial polinators.

    Black Ankle Vineyards

    4.3(199 reviews)
    12.4 mi
    $$$

    We are long-time members and things have changed consistently at Black Ankle and always for the…read morebetter! The vineyard always will be a beautiful place to enjoy great wine, people watch, enjoy well behaved dogs, and break bread with friends and family. The creation of the patios through and beyond the pandemic was a great move. The vistas never disappoint, the charcuteries boards with fresh baked bread have always complimented the wine well, the food trucks and various vendors have always been fun, but a piece was missing. That piece has been added! We were pleasantly surprised to find The Terrace Kitchen by Chef Tony Castellon delivering an elevated menu with options from homemade chocolate chip cookies to The Amalfi Toast featuring a personal fav boquerones. There are options on that menus that are to die for including veg options as expected. Note: There are chilled vegan options inside ask the desk. We enjoyed the Mediterranean inspired with Japanese twist Char-Siu Skewer with ponzu aioli, and lemon wedge dipped in a (chili, paprika, cumin dust?) was perfect to balance out the skewers. Damn tasty lamb and beef the squeeze of the lemon and spice perfected it. The Crispy Potatoes were a delight, not too heavy or greasy, nice char, and full of flavor delivered by the lardon, green onion, and melted Gruyere . Very satisfying, would order again. The Amalfi Toast is a do not miss IMO. For the uninitiated, boquerones are Spanish white sardine filets cured in acid then packed in olive oil. Unlike the premium salty boney tinned sardines available in the US, the result is a delicate cured white sardine filet over toasted focaccia coated with whipped buffalo milk garlic butter and fresh herbs. Outrageous food my friends, just delicious. Thank you Chef! Your CA roots are showing. The chocolate chip cookies were very good. We missed the duck taco special on the board which I would have tried no matter what. If it was a confit duck taco, well IYKYK. So kudos to Black Ankle Vineyards and Chef Tony Castellon. The future is bright with this new partnership. Looking forward to returning more often to catch live music and enjoy it all. P. S. Heather Aubrey Lloyd performing solo on guitar and playing many 79's and 80's covers was a great addition to our experience. Please tip these performers, you can hit her up on her website if you did not bring cash: https://heatheraubreylloyd.com/tipping

    Representing the DMV runner-up to out of town pick for letter B for 2025, B is for Black Ankle…read moreVineyards. My girlfriend & I visited Black Ankle on a Saturday in September 2025. We were out somewhat in this direction, and there was a Meetup group going here, so we thought to check it out as it's rare we ever go to a winery as it's normally out of the way, more likely of an occurrence when on a vacation. We took some crazy back roads from where we were in western Howard County, through Carroll, & into eastern Frederick County, where Black Ankle is. We went to the bar inside to get wines. I got a white wine; I think Chardonnay, and I think my girlfriend got a sweeter Rose or something like that. Both were delicious, but we preferred our own more. We sat outside in a nice patio area. We were in the hot Sun on that sunny day, but that was cool with me. We learned of a tour going on, which we got in on. The tour guide who wore an Italian flag bowtie was entertaining and informative. We walked around the vineyard, going inside the cooled storage areas, centrifuge area where the wine is mixed, etc. We even saw some of the old wines they had made from years earlier. We saw sheep dogs, which protect the vineyard from pests, which were cute. Overall, this is a high quality winery with plenty of nice outside & inside seating.

    Photos
    Black Ankle Vineyards - Group doing an outside tasting at Black Ankle.

    Group doing an outside tasting at Black Ankle.

    Black Ankle Vineyards - Indoor seating

    Indoor seating

    Black Ankle Vineyards - The details!

    See all

    The details!

    Burnt Hill Farm - Kitchen area

    Burnt Hill Farm

    4.7(32 reviews)
    12.7 mi
    $$$

    A gem in the DMV! I visited in a Sunday afternoon with a reservation (highly recommended). We were…read moreimmediately greeted by a team member, checked in and served a glass of champagne during a short wait for our table. We were able to walk around the grounds and enjoy the amazing view. The interior dining space was open and bright. Our server took our picture outside restaurant which was given to us a souvenir with a thank you note at the end of our reservation. The culinary menu of Asian American influence and is farm fresh. The dishes and pizza we enjoyed were phenomenal. This is a winery restaurant so while there are smaller bites they have a full lunch/dinner menu and the entree plates are of a good portion size. We started with a hand cleanse towel scented with lemon grass and chose our flights in which there are flight offerings from Burnt Hill Farm as well as their sister winery. They also have a non alcoholic flight so all can enjoy. The reservation is for three hours which is more than enough time to enjoy dinner and a flight or glass of their wines. A truly amazing experience I can't wait to visit again! Free parking $$

    I'm not a wine girly but the champagne bubbly when you stove! YUMMMYYY the bottle is $75 and that…read morewas above my spending budget for the day. Pizza was thick and not really flatbread. But good nonetheless. I don't like the coffee. I tried something new. Never again. Ambiance is lovely for photos and a girls day out. Service was slow but the atmosphere made it comfy. The decor it beautiful. I didn't taste the curry but it was a hit for the table. Be sure to make a reservation.

    Photos
    Burnt Hill Farm - Roasted tomato focaccia pizza

    Roasted tomato focaccia pizza

    Burnt Hill Farm - The Lounge

    The Lounge

    Burnt Hill Farm - Interior of the main building

    See all

    Interior of the main building

    Tin Lizzie Wineworks

    Tin Lizzie Wineworks

    4.0(2 reviews)
    5.8 mi
    $$$

    I had the wonderful pleasure of visiting this awesome place with a group of amazing people. It's…read moresimply fun to learn how to make wine, and actually make your own! The wines we tasted were very good. I enjoyed the Rosé and Chardonnay. Good stuff! It was a perfect day! The drive out to the property was gorgeous! I highly recommend it if you want to do something a little different and learn about the winemaking process.

    You'll never just drive by this place ... but you should definitely seek it out. Winemaker Dave -…read morewho trained at UCDavis, and has won a bunch of awards for his wines - opened this local, hometown version of Crushpad. Like Crushpad, he sources grapes from California (among other places), and will work with you to make your own barrel. He doesn't offer as many sources as a big VC-backed operation like Crushpad; on the other hand, you can get half or even quarter barrel; and possibly use local grapes if desired. Dave will help you make anything from your basic pizza or burger wine (from Lodi or central valley grapes) to a high end Napa cab (from designated vineyards) or Rhone ranger. And you can put your own labels on the bottles. Dave's been making wine for 40 years, but just getting this Wineworks operation started. It's a cool little place. He gave us a tour, explained the equipment, and popped a bottle of his own 2005 Stagecoach Vineyard Cab (Napa), while telling us about the notorious Girls for Swirls wine club that's making a Zinfandel with him right now. He's gotten a number of awards for the Cab, and it certainly was a very respectable wine. A group of us may go together on a barrel. If so, I'm hoping the real experience and end product result in an upgrade to 5 stars. It's showing potential ...

    Photos
    Tin Lizzie Wineworks
    Tin Lizzie Wineworks
    Tin Lizzie Wineworks

    See all

    Boyd Cru Wines

    Boyd Cru Wines

    4.7(26 reviews)
    16.3 mi

    We came here for the first time for our Anniversary. I had this place on my Yelp list to try and…read moreonce we had to rearrange our plans I decided we would come here to explore this black owned business. I had never been to this location and to my surprise this place is located inside of an establishment that has multiple specialty shops. The decor alone expressed love and care along with meeting one of the owners. She came across as warm, inviting and willing to share parts of journey in the wine space. We had great conversations with the staff about wine pairing, where the grapes are harvested so much more. The staff were so knowledgeable. Now, most of wines are dry as I am a sweet kinda girly. I was able to find a wine that fits my tastebuds. We ordered a charcuterie and flatbed pepperoni pizza. It was a great way to celebrate our Anniversary for lunch date before putting up the kids. Will most definitely return.

    Overall: small wine bar inside of Savage Mill, delicious wine, flights available, kind service,…read moreexcellent and fun ambiance, good music, they display and sell local art and locally made goods, single stall inclusive restrooms It's taken me longer to get here than I would have liked because they don't have very extensive hours. They close pretty early for a wine bar. My friend and I went on a Sunday afternoon and had an absolutely lovely time. I love that they offer flights ($35 for 3). I tried most of the wines and really enjoyed them all, but serenity was my favorite. I loved how they incorporated goods and art from local business owners and artists. They had a small food menu with dessert flights, snacks, and charcuterie. We really enjoyed the playlist and the variety of places to sit. It was pretty empty while we were there.

    Photos
    Boyd Cru Wines
    Boyd Cru Wines
    Boyd Cru Wines

    See all

    New Market Plains Vineyards

    New Market Plains Vineyards

    4.6(19 reviews)
    14.7 mi
    $$$

    I saw a sign for a winery while en route to another and decided to make a stop. I hadn't heard of…read morethis place and had no idea what to expect. Let me get the "bad" out of the way first, and note this is still a five-star review. You drive up a gravel country road to a small building that houses the tasting room. It's the smallest tasting room I've ever been in, and very simply decorated: a few beautifully framed pieces from the farm's history, some antique tools, and that's about it. This isn't going to be your upscale winery experience. If you're looking for Napa or Bordeaux vibes, you're in the wrong place. The single guy behind the counter turned out to be the owner. He mentioned that his wife usually runs the tastings, but she was on vacation. He was fantastic, fun to talk with, knowledgeable from both a production angle and a "yes, I actually drink these wines" perspective, which is surprisingly rare. He even spoke warmly about nearby wineries, treating them as colleagues rather than competitors. It's always refreshing to meet a winemaker who genuinely enjoys other people's wine. As for the wines: we tried all twelve. A couple were still young and could use a few years in the bottle, but they showed a lot of promise. I didn't care for the Muscat, but most of the others were excellent, and I had a hard time choosing which bottles to take home. Be sure to try the "Trop Elyts"; it's fantastic, and kind of port like. I'm not usually a rosé fan, but their take on it was so unique I bought a bottle of that, too. The farm itself dates back to the 1700s. George Washington probably slept there (he slept everywhere). It's full of character and history, and well worth the stop

    Overall: small, casual winery, decent wines and prices, with okay service and a single restroom…read morethat you have to go outside to enter They have indoor seating, a covered patio, and outdoor seating. There is not strong AC anywhere there. The indoor seating is very small and feels like you're in someone's grandma's living room. Tastings are done in a flight with plastic cups, not one at a time in a glass. We did enjoy the wines and eventually enjoyed talking to the one employee who was there, but it was a rough start. When we entered the tasting room we were the only people there except for one other man. We had to initiate conversation with him to determine if we were in the right place and if we could get a tasting. It was confusing and we didn't feel clear about what to do or welcomed. I did enjoy the Rich Forest Chard, the Rose blend, and the Hogshead Red. It was interesting to learn about the residual sugars and how their rose is different. There is a cemetery on the premises which was an interesting choice.

    Photos
    New Market Plains Vineyards - Bathroom

    Bathroom

    New Market Plains Vineyards - Wines and tasting trays.

    Wines and tasting trays.

    New Market Plains Vineyards - Some other historical artwork.

    See all

    Some other historical artwork.

    Windridge Vineyards - Winemaker Nick Maliska inspecting the vines.

    Windridge Vineyards

    4.3(233 reviews)
    21.1 mi
    $$

    Celebrated my birthday here with friends yesterday. It was a really gorgeous day out and everyone…read morehad a great time! Reservations were made weeks ago because this place is quite popular. Please be mindful that parties of 9 or more require a $100 non-refundable fee (doesn't go toward the bill). They have alot of seating options! There's signs up saying that it's 21 and over but I did see a few strollers. Maybe it's different for private events?! Call ahead to find out! One great thing about this place is that they allow you to bring your own food! Many places don't. They also have a kitchen with a few options. A few of my friends got the flatbread and the crab cakes, which they enjoyed. We tried a few different wines. My fave was the still rose! Cheers! Until next time!

    It is a quite nice winery with good quality white wine…read more 1. Reservation: absolute must. You will not get a table otherwise. 2. Wine: 4 stars Quite good for this region. We have tried literally the entirety of the menu! I prefer their white wines and very crisp and current weather appropriate. They have a rule of 1 bottle per person only. If there are 5 of you and you want to buy 6 bottles, it will not work! 3. Food: they have very good warm bread, charcuterie, flatbreads and food options. They are quite good especially for a winery. 4. Interior is nice and simple. Outside seatings don't always have an umbrella, so make sure you clearly state it when you reserve. 5. There is a grocery store with very good sushi just 4 mins away if you want better food!

    Photos
    Windridge Vineyards - Our staff is here to serve you!

    Our staff is here to serve you!

    Windridge Vineyards
    Windridge Vineyards - Grapes on the vine

    See all

    Grapes on the vine

    Penn Oaks Winery - wineries - Updated September 2026

    Loading...
    Loading...
    Loading...