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Harold Black

4.2 (22 reviews)
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HAROLD BLACK ATMOSPHERE

What's the vibe?
Casual
Dogs allowed

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Meatballs, calamari, crab cakes
Sydni R.

Nice speakeasy. Visit here after dinner and had a good time. It's pretty small and if you don't have a reservation be prepared to wait, the place is small so if you arrive on a night that's busy you will have a wait. It's pretty dark (I guess to keep up with the whole speakeasy theme) but it is a pretty cozy spot. The food isn't too bad, but nothing to really brag about. The drinks are good as well. To be honest I'll probably be back when I'm the area and I just want a cocktail with someone.

Virgin mojito
Ranjini S.

My first speak easy experience. We sat at the bar and were able to order dinner from the full Italian restaurant menu. The place has a really cool vibe and the bartenders were fun to watch and chat with. I don't drink alcohol but they made me a virgin mojito. The place has great ambience and I loved the decor too -- especially the glass and metal screen at the back of the bar.

Booth seating
Natalie C.

In the basement below Acqua Al 2, Harold Black is a bar/speakeasy for a fun late night spot. I was definitely expecting "more" when you call yourself a speakeasy, but it was fine enough for an after dinner drink. The bartender didn't seem to know much of drink making and was confused when we shared the ingredients of a drink. Ended up getting poured enough port for three glasses so it all worked out in the end. Will probably try another place next time.

Bar area

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3 months ago

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1 year ago

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1 year ago

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4 months ago

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2 years ago

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2 years ago

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1 year ago

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2 years ago

Helpful 6
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2 years ago

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3 years ago

Helpful 1
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1 year ago

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2 years ago

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2 years ago

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1 year ago

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2 years ago

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3 years ago

This place is an old 18th century building with a speakeasy in the basement. The service is top notch along with the happy hour menu.

Helpful 5
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1 year ago

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3 years ago

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3 years ago

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3 years ago

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3 years ago

Best "speakeasy" in the DMV. Atmosphere is vibing with GREAT tunes and quality drinks. Just don't tell the tourists!

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Review Highlights - Harold Black

It's an intimate speakeasy bar in the basement under Acqua al 2; you enter from a side door on Church Circle.

Mentioned in 3 reviews

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In a shopping center so plenty of parking. We came here around 12:30 on a Saturday and they were…read morevery busy. There is some seating outdoors, a good amount of seats indoors and bar seating. For a table for 3, it would have been about a 25 minute wait but there was plenty of seating at the bar open so we opted for that. I don't believe they take reservations. Bartender was great and service was fast. Ordered a couple of beers and for food, we opted for the Honey Old Bay Wings, the Crab Cake Grilled Cheese and the Slammin' Salmon. Everything came out fairly quickly. The wings were amazing! Very tender and hot and the Honey Old Bay Ratio was perfect. I loved my Slammin' Salmon sandwich and the Crab Cake Grilled Cheese was also good. The portions were large and we had a great time here. Would definitely recommend coming!

This place has been a favorite of ours for so long and I'm not sure how I haven't reviewed it…read morealready. The place is in a prime location with plenty of parking outside. On a good weather day you can eat inside or out as they put tables outside for more customers. They have a small sports bar if you want to watch the game but most of the seating is for lower tables. There are not a ton of tables so on busy days we recommend coming earlier than you think. Service is always on point. We have been served by repeat waiters/waitresses as well as the owner of the place many times over our visits. And if you need something you can always call over a nearby waiter. The food is also good. We recommend upgrading to the onion rings which may be the best we've ever had. We also love the dry rub wings which always come out hot and fresh. The slammin salmon and the aloha chicken are our absolute go tos and they are always delicious. You can even ask for them on Brioche or as a wrap. All in all we love this place and continue to make it a staple when we are close by and even when we aren't!

Vin 909 - THE SPOTTED PIG Tomato Sauce, Mozzarella, Provolone, Parmesan, Wild Boar Meatballs, Soppressata, Basil

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Great people, great atmosphere, and prices that are actually fair, which is rare these days. This…read morespot fills up fast, so if you're trying to walk right in and sit down, get there early. Trust me, it's worth it. They've got a small bar area that seats about 4-6 people, which is where I sat, and honestly that's the move if you like a lively vibe. Now let's talk about the pizza--amazing. Fresh, flavorful, and one of those meals where you catch yourself still thinking about it later. I enjoyed every bite and could've easily gone for another round. Overall, this place delivers: good energy, good food, good people. Definitely a spot you want to keep in your rotation.

On a busy weeknight, I wandered into Vin 909 with my partner. It's a small seeming place, on the…read moreside of a relatively quiet road, with ample parking. It's supposed to be a wine bar, I guess, and the wine is their main focus, though they are also apparently well known for their pizzas. Despite it being busy, we were seated pretty quickly in the back area, and were served quickly. Our waitress was great, and offered a lot of good drink and food suggestions. I love the way the wine is broken down. They've got three categories, which are snarky grouping by price. I am drawing a blank on the names of the categories, and they're not on the website, so .... they were something like, "Wallet Friendly Wines," "I can splurge a little," and "Money is no object to wine!" Theirs were probably better and more creative -- dock me one star as a reviewer for not remembering. :) The wines were good. I tried two different ones, including an unusual "orange" wine, which is a white wine left to contact the skins. It was a little fruitier than I usually like in a white wine, but it was good still. The food for me was where it fell down. I ordered a charcuterie plate, which was honestly kind of skimpy for the price. I also got a burrata, which is served with "harissa roasted carrots." The harissa was incredibly spice forward, and... burrata is a delicious, but delicate cheese. The carrots and harissa basically contaminated it and overpowered it. They might as well have dipped it in coriander and cumin. That's fine if you want to eat coriander and cumin, but not if you want burrata. My pizza was the biggest let down. It's a "rustic" style pizza, but it frankly translates to "poorly made." It's a good size, roughly oval pizza, with very thin, crispy crust. Like a giant cracker. It's then cut into 16 pieces (give or take, don't quote me). Some of those pieces had /nothing/ on them. Like, just crust. No cheese. No sauce. No toppings. Others had just sauce. I'm not a big fan of pizza, but when I eat it, I expect every piece to have sauce, cheese, and toppings on it... if I wanted to eat just crust, I'd just ask for a pile of aperitif crackers. Great atmosphere, good drinks, fair price, but ... terrible food. If I lived nearby, I'd stop by for a drink now and again, but I wouldn't eat there.

Parley Room - Main bar area

Parley Room

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We were here for the 4th of July cookout on the patio. It was Awesome! They had a really nice…read moresetup. This was a buffet which included desserts as well as a nice selection of food. Everything tasted great for the most part. Service was great as well. The outdoor buffet cookout was $20 tickets were purchased on eventbrite. They also had holiday drink specials at $2.49 which was a good deal. They also sold smoked oysters at $1.00 each & the server and bartender was very helpful and friendly. We really enjoyed this event. We would like to go back and check out the other drinks on the menu as well as the food. Definitely bookmarked this spot for a return visit. There is a parking garage about three blocks away. We paid $12.00 for about three hours. Not bad at all.

Modern, dark, speakeasy vibes on the inside with windows overlooking the Main Street, and a…read morespacious outdoor deck quite literally in the shadow of the gorgeous Maryland State House. All housed in the historic Capital Hotel, newly renovated in November of 2022. The atmosphere here is immaculate. It is a must see when enjoying the sights of Annapolis. My girlfriend and I stopped in on a Thursday afternoon after touring the State House. We each ordered the Monkey Smoke (Penicillin), and she ordered a small plate with avocado and lump crabmeat, which we ordered just in time as the kitchen closed between 3 and 4. The standout of the day for me was the old fashioned, made with plum bitters. One of the best old fashioneds I've ever had. The servers were all very friendly and quick. We will definitely come back the next time we're in town, and definitely recommend this to others.

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Preserve - Pork Terrine

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At Preserve, consistency is not the point, evolution is. Each visit feels slightly different,…read moreshaped by a menu that shifts with the seasons and refuses to coast on familiarity. That restlessness works in its favor. The space is compact, almost disarming at first. Then it settles around you. There is a quiet intimacy to the room, the kind that feels less designed and more lived in. It leans closer to a welcoming home than a polished dining room, without losing its sense of purpose. The food carries that same balance. Thoughtful, seasonal, and just unpredictable enough to keep you paying attention. Cocktails follow suit, measured and deliberate, never an afterthought. For Annapolis, where good options are not exactly rare, this place still manages to separate itself. It belongs firmly in the top tier of the city's dining scene, and it earns that position every time it changes the menu and starts over again.

Located on Main Street with bar, inside/outside seating. Wonderful decor and a great drink menu…read more Food menu was great as well and not too overwhelming. This is a place that has lots of drinks and foods that have some unique and creative flavor profiles. We were greeted immediately and sat at bar. Server acknowledged us quickly and was very friendly. Checked on us throughout the time we were there. Ordered a tequila cocktail that was amazing. Highly recommend!!! So so good. Their cocktail menu has the spirit and then a description under of the drink. No actual names. Lots of interesting drinks. We grabbed a couple of apps. Got the pork bites and smoked fish dip. Both were tasty and had interesting flavors that worked. The portions were great. You can tell that great care and thought is put into to the menu. The burger and fries looked amazing - on special and lots of people around us were ordering it. Would have ordered that if we were eating a bigger meal. This is a gem of a place. Truly crafty food and drinks. Highly recommend trying them out. Would come back again.

Harold Black - salad - Updated May 2026

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