Harold Black - Annapolis
236 Main St, Annapolis
(410) 304-3353
Recent Reviews
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This place used to be good but it seems to be going downhill. Sounds like the chef left and it’s very apparent when you order the food. It’s lacking the authenticity it used to hold
6 of us were crammed into a u shaped table that was too small. Everything was VERY expensive. Food was good! Way too noisy and hot for 6 for dinner
Intimate bar
It truly felt like a speakeasy with the hidden door and the lighting/space. However, one big complaint—the music was SO loud which made conversations even louder. I like speakeasy bars for their ambience and intimate settings and while the aesthetics gave speakeasy vibes, the music and noise level definitely did not. A bit disappointed.
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!
Our Bartender worked wonders for us as late arrivals at 10:30pm on a Friday night. Welcome to the best sour in Annapolis!
Great service from Lenny and Jojo! Highly recommend the burger on the bar menu, it may be $20, but it’s worth it! Cocktails and vibes were on point.
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
Restaurantji Recommends
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.
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