Harold Black - Annapolis
236 Main St, Annapolis
(410) 304-3353
Recent Reviews
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Great service at the bar. We ordered food from the upstairs menu and it was excellent. Cocktails and wine were also great. Will be back!
Sigh. We loved this place when it was in DC and saw the negative reviews but wanted to see for ourselves. Doorman and servers are plenty nice but there is no cool factor at all, and the cocktail menu left a lot to be desired. They were very sweet to give us free bubbly for our anniversary but we couldn't even drink it because it wasn't good, so we tipped well and left. Lots of potential, as the staff is great, but needs a lot of work on menu, decor, the concept as a whole. Bring back the vibe they had in DC and it would be amazing!
Very shocked at the food & the service we received. We've dined here before and have never had the experience that we had on Sat night. No one in our party enjoyed their meal. It will be a while before I return.
Always amazing food! And the drinks are perfect. Sometimes it gets a little loud
Haley was our server and she was such a wonderful server. The food was some of the best pasta I’ve ever had, I had the gnocchi. Overall one of the best dining experiences I’ve ever had
The ambience and vibes were pretty cool. Service started off good, but once we closed after one round of drinks our server brought the wrong tab and then disappeared for 20 minutes and we had to close out at the bar. The drinks were kind of disappointing for a cocktail bar, unfortunately.
We had a fun visit at Harold Black's speakeasy. It started with the somewhat hidden entrance down the cement stairs - what were we getting into? We enjoyed the interesting drinks and food. The pasta sampler and the trio of salads were delicious. It was very dark in the bar area and it was noisy but our group of five had a lively conversation regardless. A good time was had by all.
Best staff in all of Annapolis! Best bartenders, friendliest, most accomadating, best food!
The girl with black hair working in the speakeasy was flat-out rude and gave off the worst attitude I’ve ever encountered in a service job. From the second we walked in, it felt like we were annoying her just by existing. No greeting, no smile — just a blank stare like we were interrupting her personal time. And honestly, we were… because she was glued to her phone the entire night.
When we asked questions, she rolled her eyes like we were wasting her time. She acted like everything was a chore — like getting a drink order right or just doing her job was somehow beneath her. At one point, she scoffed when we asked if we could close out. Scoffed. It was unbelievable.
She made the whole experience uncomfortable with her nasty attitude, sarcastic tone, and complete disinterest in being helpful. It’s one thing to be inattentive — it’s another to make your customers feel like a burden. There’s absolutely no excuse for that kind of behavior. If this place wants to keep any sort of reputation, they need to seriously rethink who they’re letting represent them.
Amazing atmosphere with incredible cocktails. We visit every time we are in town.
Restaurantji Recommends
Excellent cocktails and wonderful service, especially if you are industry-minded. Lenny and Jo-Jo are absolute killers, and I’d trust my them the life of my drinking. Try a Bobsled.
Such a cute spot, completely hidden so it took us a minute to figure out where to go but that just added to the whole experience. We thoroughly enjoyed the drinks, service was amazing, food was great too but we only had appetizers. Highly recommend this spot.
Have gone twice and had an amazing experience both times! We ordered the pasta tasting menu and the salad trio off of the restaurants menu and both were wonderful! Mocktail I had was great as well!
Awesome bartenders and staff. The cocktails are awesome and the food is great
Living in D.C. and frequenting Harold Black on Capitol Hill for years before they closed during COVID, my buddy and I made the 30-minute drive to Annapolis to visit Harold Black, also in Acqua al 2. It was a different experience than the one in D.C.
What's the same is that they are both in a good Italian restaurant, but the Annapolis one if in the basement and more of a bar than an actual speakeasy. When we went, it was crowded so we're glad we had a reservation.
Service was great! Our server was hilarious, but not as knowledgeable on cocktails. The menus were very basic.
Our drinks were not bad, but not at the level of the D.C. Harold Black. I appreciated the Maryland hard cider on the menu.
We're glad we went, but the Harold Black in D.C. was special.
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