Going to a wine bar should be like a mini vacation to get introduced to unknown wines, wineries, and wine regions. Read on for some of the best Maryland wine bars.

A good wine bar experience is right up there with brunch. Both are good ways to elevate going out to eat and drink. Going to a wine bar should be like a mini vacation to get introduced to unknown wines, wineries, and wine regions. I love visiting Maryland wine bars, which help me continue my wine education in a fun way. I’ll share my favorites from Ocean City, Baltimore, Annapolis, Bel Air, and Havre de Grace and why they make the list.

Close to Home

A new favorite, Bacco Italian Winebar, is just up the road from my home in Perry Hall. Three partners own this Italian eatery, with two of them from Naples, Italy. Inside, Bacco is well-decorated, modern, clean, and inviting. Our first meal was delicious, and the wine list was ample.

Linguine Seven Fishes is a popular entree at Bacco Italian Wine Bar. Photo by Kurt Jacobson

It wasn’t until our third visit to Bacco that a waitress tipped us off on the Wineemotion wine dispenser in the bar. She said, “I’ll activate a card that you insert, then you can choose from 16 wines.” We had seen this kind of wine dispenser before but needed to familiarize ourselves with the self-serve variety.

Choosing from the 1 oz., 3 oz, or 6 oz pours of the available wines was fun. Each bottle of wine has an informative card above with the name of the wine, tasting notes, food pairing, and producer. We loved trying several 1 oz. pours before committing to a larger size. Since then, between their attractive wine list and the excellent menu, we’ve been back often.

The Wineemotion by the glass dispenser is one of my favorite ways to taste new wines. Photo by Kurt Jacobson

Our dog Sophie loves to go with us on warm days for an outdoor meal. The patio is away from busy roads, so it’s quiet and comfortable. All customers get Bacco’s delicious bread and olive oil to start. We like the calamari and duo dipping sauce appetizer, which is always served piping hot and addictive. Our favorite entrees are orecchiette with sausage, raviolone Sofia Loren, and fettuccine Zafferano with shrimp, scallops, crab meat, and a decadent saffron cream sauce.

Pairings Wine Bistro, a Maryland Wine Bar

Another Bel Air wine bar choice has recently expanded. It has three dining rooms, a large bar, and an outdoor seating area for all-season use. Pairings Bistro sources as much as possible from the local area to highlight the season. They source from some of our favorite suppliers. They get greens from Third Way Farm, bread from Cunningham’s—one of the best bakers in Baltimore, Crooked Creek sausage, and other seasonal meat and produce.

We got the last two seats at the bar for Friday happy hour at Pairings Bistro and settled in for wine and an appetizer. Photo by Kurt Jacobson

Notable events on their website recently included: Whiskey Brawl Dinner, Easter brunch, Spanish Wine Dinner, Mother’s Day brunch, Italian Wine Dinner, and Father’s Day brunch. They have a Market and Café menu for lighter meals and to-go items. Their happy hour is well-attended, especially on Friday. Discounted food and drink items include arancini, mussels, and flatbreads, plus beer, wine, and cocktails discounts.

The Vineyard Wine Bar

I’ve never seen a Maryland wine bar serve so many types of WBTG (wine-by-the-glass) as the Vineyard Wine Bar. On any given visit, they have 80 6 oz. WBTG to choose from and 70 in the 3 oz. size. Unlike some of the wine bars on my list, this one doesn’t offer any free tastes.

What’s not to love about a glass of white wine and broiled lobster tail? Photo by Gabby Williams.

My wife and I usually try a few 3 oz pours to get the most out of their extensive selection. We love their living room-style lounge area on the other side of the bar area. The comfy sofas and chairs are perfect for several friends to gather and enjoy wine and appetizers. The Vineyard gets two thumbs up from my wife and me for wine and food.

The Baked brie at the Vineyard Wine Bar is a great way to start out. Photo by Kurt Jacobson

I asked the owner Joe Lertch if their menu changed with the seasons, and he told me, “Yes. We actually change it more than with the seasons. We always seek local and imported products and unusual offerings from distributors and importers.” Their baked brie is possibly the best in Maryland!

Open Wednesday through Sunday, they have a faithful following, and reservations are encouraged as this Wine Enthusiast award winner fills up regularly.

Red Red Wine

I often hum the UB 40 tune Red Red Wine when I enter this Maryland wine bar on the downtown Annapolis main drag. With over two dozen WBTG and several flights, Red Red Wine Bar is one of my favorites. They also offer WBTG from a tap. They say, “This is the closest you can get to actually visiting the winery and tasting from the barrel or tank.” It was at Red Red Wine Bar that I discovered how good wines from the country of Georgia can be.

The wine flight and cheese board we had at Red Red Wine in Annapolis. Photo by Kurt Jacobson

The menu includes appetizers, pizzas, salads, sandwiches, and more. Check out their happy hour M-F 3-6 p.m., for reduced-priced appetizers and drinks. I usually park at the Hillman garage, but until it reopens from the 2022 rebuild, I am looking for on-street parking.

Maryland Wine Bar Options in Baltimore City

Not all of my favorite wine bars are wine bars. However, these Baltimore restaurants deserve mentioning because they have a bar and excellent wines.

Tapas Teatro is next to the Charles Theater, our favorite movie theater for Indy films. What a treat to be able to get yummy tapas and quality wines, including natural wines at their bar. The owner Helmand Karzi often greets customers at the entrance and helps guide them through the wine list. Grab a table or seat at the bar and take a trip to Spain through food and wine. They also have an outdoor dining area on the Charles Street sidewalk. Be aware, they don’t take reservations.

Tapas Teatro outdoor dining is usually full in the summer. Photo by Kurt Jacobson

Another Spanish-themed restaurant with superior wine is La Cuchara. The large wrap-around bar is popular for tapas and WBTG. Sundays are our favorite day to visit for half-off wines by the bottle, but only those priced above $100.

This lineup of rose wines was a special wine flight on a hot summer day. Photo by Kurt Jacobson

Parking is easy, free, and close, a rarity in Baltimore City restaurants. Tell their wine guy, Red, I sent you, and he’ll probably say, “who sent you?” Or he might remember me. Either way, Red is a knowledgeable sommelier who knows their wine list well.

Harbor East

Cinghiale is one of Baltimore’s best Italian restaurants. Inside Cinghiale are three venues; the enoteca, the osteria, and the special event rooms. Although my wife and I have dined at Cinghiale several times over the past 13 years, recently, I decided a meal at the bar was in order for research purposes.

Wilmar was our bartender and took exceptional care of us. We requested to taste two wines before committing to a full 6 oz. pour, and it was no problem. We ordered a Prosecco, and just after the wine arrived, their delicious house-baked bread and olive oil were delivered. For dinner, we chose the $71 Prezzo Fisso menu—a four-course tasting menu—and it was fabulous.

Cinghiale salad and wine in the enoteca. Photo by Kurt Jacobson

We moved on to a 6 oz. pour of excellent valpolicella ripasso to pair with short ribs. Since this was a research visit, I tried yet another red wine, Proprieta Sperino, a nebbiolo from the Piemonte region. Both red wines and the short ribs were so good I was plotting a return visit.

A bottle of Proprieta posing next to a glass of the same at Cinghiale’s wine bar. Photo by Kurt Jacobson

Grand Cru Market Bar

Belvedere Square is a food hall-type eating and drinking establishment. Inside are several tasty eateries and one bar/liquor store named Grand Cru Market Bar. It has been a presence at the Square for many years and has undergone physical changes and new owners. In 2022 Grand Cru expanded the bar to occupy the space once held by an Italian grocer.

A glass of Il Farneto “Giandon,” an organic Italian wine that went well with Pad Se Ew. Photo by Kurt Jacobson

On my most recent visit, I tried the WBTG numbered 10. I like that the bartender will allow you to taste before you buy a glass of wine. I tried a taste of the Chehalem rosé, and even though I liked it, I thought something else might pair better with a bowl of Pad Se Ew from Thai Landing. The Jaine sauvignon blanc won the contest to pair with lunch and was perfect to go with spicy Thai food.

This tasty sauvignon blanc paired perfectly with lunch. Photo by Kurt Jacobson

With over 12 Belvedere Square eateries to choose from, find your lunch or dinner item and bring it to the Grand Cru bar to enjoy a winning combination. My favorite eateries are Thai Landing, Koba Korean BBQ, and Atwaters.

For the Love of Champagne

The Bygone is a restaurant at the top of the Four Seasons Hotel in Harbor East, a Baltimore neighborhood. They excel in views and Champagne. The last time we were there, the Champagne bottle list was around 100! Their bar offers the best view of Baltimore City and is great for a glass of Champagne, wine, beer, or a cocktail, especially at sunset.

We picked a clear evening for dinner and wine at The Bygone in Baltimore. Photo by Kurt Jacobson

In the town of Easton over on Maryland’s Eastern Shore is a small but impressive Champagne and scotch bar named The Stewart. Serving single malt scotch and Champagne by the glass or bottle, this is one luxurious place to sip the best. The Stewart also serves small plates from their shared kitchen with The Wardroom, and the food quality is top-notch.

The Stewart is one of our favorite places for a glass of Champagne. Photo by Kurt Jacobson

One could spend up to $1,000 for the best Champagne, scotch, and caviar, but we usually get by with their amazing curry cashews and a glass of Champagne for under $50. Not cheap, but you feel like you’re in a place of royalty when visiting The Stewart.

To the Beach

Ocean City is a Maryland beach town and playground on the Delmarva Peninsula. In 2022 I discovered a fun Maryland wine bar and bookshop combination called appropriately The Buzzed Word. What I like best about this hot spot in a strip mall is they specialize in natural wines. Mickie Meinhardt, the owner, is devoted to getting the word out on organic, biodynamic, and natural wines. She has stocked an impressive selection of wine from all over the world, specializing in Spanish, but also includes France, Italy, Austria, and other wine regions.

Mickie, the owner of The Buzzed Word, with some of her wines by the glass. Photo by Kurt Jacobson

Grab a seat at the bar and try one of several WBTGs. If you like what you taste, it’s good to know you can buy a bottle of the same wine to take home. All the bartenders are LBGTQ+, and the bar is open to everyone; it is a great bar scene for all. The books for sale are also quite good. Perusing her list led me to a great wine book titled, To Fall in Love Drink This: A Wine Writer’s Memoir by Alice Feiring.

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Last Pour

I hope to try other Maryland Wine Bars soon. Until then, I hope this list gives you a starting place if you are visiting or are new to the area. Let Wander With Wonder be your guide when looking for wineries to visit or great places to taste wine.