Terrific historical venue for grabbing a bite to eat and drink. Convenient location in the center of town. There's outside and inside seating. There is a bar area and various spots throughout that have dining room seating. We were partied in a garage so unaware of ease of parking in this area where the restaurant is located, but would assume it would be difficult. This is an old tavern and that's the vibe!! Super friendly host at the door who walked us to the bar area. He was great. Once seated, we ordered a Skinny Dip which was lemonade and iced tea vodka. Very good. Also ordered the spicy pickled Bloody Mary. Was okay. Had to ask for some horseradish and added some hot sauce. Wouldn't recommend. Only grabbed an app and we picked the tuna wonton (not sure of exact name). The pic is only showing half of it. It was absolutely delicious! Highly recommend. They do have a bar vibe and even have Keno. They do have specials - burger and crabcake sandwich that also came with a beer. Good deals and quality food. read more

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What can I say? Great spot to watch the O's game, happy hour deal is nice and affordable. Staff are friendly and kind.

"Tired" Drinking Establishment with Good Oysters Apart from the tavern's 275-year history in Annapolis, Middleton's main distinction is that it remains a tired bar for weekend tourists. The tavern features Oyster Shooters with a Natty Boh chaser and turn of the century tables on its front patio with views of Ego Alley. Not going to win any James Beard awards and likely a one and done stop for this local. read more

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This was the first little local spot by the water I went to being in Annapolis . Let's get into it . ( as a Oakland girly that loves seafood ) Sooo parking is hit or miss it's right by the water. Very touristy but also local spot . And I say that to say because of the vibe you get once walking around the waterfront and into the restaurant. But from the outside it's a big old brick building. We saw the menu on the outside and said let's go . Now here's my thing . I only came here for 3 things . lol so for my first experience I enjoyed my meal . I got dozen oysters which were fresh plump creamy oysters way bigger than I expected but highly appreciated lol . I got a Bloody Mary which was also made very nice the right amount of everything . And fries which came out first and were fresh hot ! Crisp . Simple but satisfying. I'd come back for what I know I want lol . Reading others reviews and also getting the vibe inside that it's a local spot that some of the entrees might be bland or simple .... I'd say they have great bar service the oysters are fresh drinks and apps are good ! Also the inside has an old school vibe inside that matches the outside but has a lot of vintage items all over it was cool to see so much I didn't even take pictures I wish I did ! This place gives local pub by the water . For my first time ( during lunch hours ) I'd come back next time I'm out there . read more

Middleton Tavern - Dozen oysters and a Bloody Mary - Seafood Near Me - Annapolis, Maryland

About 90 minutes after I ate a crab cake at Middleton's on Saturday May 9 2026 around 3pm I had projectile vomiting lasting for 30 minutes after which I felt much better. That's food poisoning, not a virus or stomach flu. It only takes a small amount of contaminated crab to cause such immediate vomiting. Very disappointing. I hope Middleton's takes this seriously and investigates. read more

Stopped in one afternoon while in town with friends for a break from the days heat, a little lunch and a cold libation. We were seated inside by the hostess walking in. An old landmatk eatery. This place is popular with the locals, service was friendly, professional and kind. Our server brought us all water glasses and then took our drink orders while we perused the paper menus. We started with a dozen of the house oysters and the fried Calamari. The oysters were fresh and flavorful but the shucker did not cut the membrane, making them difficult to eat. The calamari was okay, a bit tough though. I opted for the fish and chips, a single piece of beer battered Haddock with a small portion of both slaw and fries and some tartar. The fish was okay, not great but okay. The slaw was a tiny serving, and the same with the french fries. At the price paid, it felt short changed with the single piece of fish and minimal sides. It served its purpose for that moment but to leave still hungry, a let down. 3 Stars - it served its purpose but there are better options in the area. 01096 read more

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Since the servers were sweet, I will give it a two. The saltiest meal and drinks I have ever had the misfortune of partially consuming. We could not eat our meals. Mushy thin crab. Next day was my birthday but I could not get out of bed my body was so swollen from the salty food. I would avoid this place and wish we had. Very sweet service. Awful food, sorry but true. read more

The 2,5 star surprised me! I was going to give 5 star... I like the ambience, fire place, decoration... It's very authentic and historical place! . The waiter who look after us was really nice! Kind helpful and with smiling face! . I like the oysters! Fried oysters was different but ok. My cocktail was under expectation! The other thing was ok. But service and the ambience that I like about the place... read more

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Recently dined at Middleton Tavern with a friend. The restaurant was pretty empty because we went for lunch in the middle of the week and it still look quite some time for a hostess to seat us. Once we were seated our server was friendly and efficient. We sat outside on the water and had a great view of the boats. The food was tasty. I got a lemon crush and she got the skinny dip (sweet tea vodka and lemonade). We shared a bunch of appetizers including the steamed shrimp, crab dip, steamed mussels, and a side of fries. read more

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The history and location are what brought us to the Middleton Tavern. We ate here about 30 years ago and remember a great time. Not much has changed since that first visit. The crab meat sandwich was served with broken potato chips and a dry, uninspired bun. It could have been elevated with kettle chips and a brioche bun at least. The Ruben sandwich was good. The beer was tasty. Overall, the servers were awesome. Cheerful, attentive and engaging service. The patio/porch is a great place to enjoy a drink and watch the happenings in town. The ambiance inside is dark and dusty. Everything needed a freshening. There's a difference between historic and tired. read more

That Donnie is something else. What a gem they have there. We drank ice water for an hour without ordering any food, and he offered to change my son's diaper and help my mom to the ladies room. That's customer service! We will def come back next time we eat at Buddy's. He is a Saint! read more

Was okay. Was one of the first places I tried in Annapolis. Got the Crab Dip and Caesar Salad with Lump Crab. The Crab Dip was great. The Crab on the salad was great, but overall, it was a little underdressed. Came back a second time (the same week) and waiter told me they were out of salad? Eventually, I got a salad and then they forgot my Seared Tuna. She never poured us any water. We had to go to her stand and do it ourselves. Not the best service. read more

...if nothing else, feel free to come here for oyster shooters. Unfortunately, that is all I have to say about this location. Jay, the server, was decent. The food, my grilled Ceaser salad wrap, was also decent. That -- is about it. I'm usually more detailed with my reviews, but this place didn't give me much to review. Bland if you will, subpar if you will. More than likely, I will not be returning. There's plenty of other spots in downtown Annapolis that are better than this establishment, if you're looking for Annapolis dining. read more

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Cool tavern. Nice outdoor seating. Food is good and not too expensive at happy hour. Service is slow but friendly. Decent tap list. Kid friendly. A place worth checking out. read more

Stopped in for a light lunch. Reminded us of a Mcsorelys south. Really liked the history and ambience. The crab and lobster bisque was fantastic! That alone will bring us back. The service was very attentive and friendly. read more

This place was so great in the past. You walk in now and it smells of cleaning supplies. The food was just okay. The pasta was mushy. The vegetables were not fresh. The meat was okay. We used to go out of our way to go here. No more. So sad. read more

I was headed to a Hip-Hop yacht cruise along with my friend and chose this place to get a small snack and the recommendation was crab balls and I was not disappointed! And that bread! Our server was awesome and friendly, can't remember his name, but I'll be back!! I want to explore other menu items! read more

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The food was served hot/fresh with friendly, helpful service in an historic structure with great decor and various settings paying homage to the history of the area and the Naval Academy. read more

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We were just at this location waiting to be seated. The waitress that was sitting patrons outside (she was short with black hair in a ponytail) was extremely rude, to the patrons already seated and towards a coworker. In addition to this, when my husband asked about a table, she was rude, shouting at us and even told us "there are other restaurants out there". Now I understand why this place only has 2.6 star review. read more

Middleton Tavern is a great location and ambiance. That said if I'm going to spend $100 for two people I can find a better place. First we were taken to an empty side room and told we could pick a table. We picked the only table for two that was set up. I liked the smoked bluefish (with ritz crackers and horseradish--authentic), but the fried oysters were encased in quite a solid thick crust it was hard to taste the oyster unless you pulled off half the coating. The fried green tomatoes should be labeled eggplant Parmesan because those were the dominant features (I assume the bottom was a green tomato but can't say for sure). There are so many places to try in Annapolis. For the price and quality I'll try some different next time. read more

I only came to this place for the recommendation of the famous oyster shoots and I highly recommend it, great combination but I recommend ordering several, the atmosphere is typical of an American tavern and the place has years and a lot of history anthe super friendly staff! I recommend sitting at the bar read more

Middleton Tavern - Shrimp Shooter - Seafood Near Me - Annapolis, Maryland

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For history, haunts and hunger - all can be satisfied at the Middleton Tavern! Whether you wish to dine out or in, there's plenty of space. Service is quick and friendly and the menu is stacked with anything you'd expect from a tavern and more! I stuck with the fish and chips as default and because I like to test out that dish for a first time visit. The fish, chips and slaw were fresh and yummy! As for the haunts, nothing spooky on this visit but apparently there's quite a history of random activity - especially at the bar! read more

Stopped in on crappy rainy April day . Was cozy warm . Excellent coleslaw. Service was great . Friendly . Had tge fish and chips , very good and arrived hot . read more

Middleton Tavern - Had a great lunch . Excellent cole slaw . Nice and cozy warm on a rainy crappy day . Fish and chips was grwat . - Seafood Near Me - Annapolis, Maryland

Family living in Alexandria, VA took us up for a Naval Academy tour...which is well worth the stop. Easy to do in a couple of hours. Staff takes You on carts...minimal walking. Had lunch afterward at the Middleton. The food was fabulous. We decided to start with oyster shooters woth their beer chaser. You can do with or without vodka...do the vodka. Of course, seafood is fresh. I ordered the steamer special off the luncheon menu. They brought them in a big bucket which more than filled my plate. Shared with four others and couldn't finish. Our table asl enjoyed grilled calamari, oysters rockafeller, fish....service was wonderful, Maddy! Maddy L was also sweet. There was so much more to be explored there. Would love to revisit again. read more

Middleton Tavern - Middleton Tavern - Seafood Near Me - Annapolis, Maryland

Came here to sit at the bar. The atmosphere is very cool and unique! The crushes here are great. The bartenders were all great and so friendly. They gave us other suggestions on places to go. Their oyster and shrimp shooters were awesome!! We ordered the mussels to much on and they were done just right. So flavorful. I'll be back! read more

Middleton Tavern - Seafood Near Me - Annapolis, Maryland

For a place to state on their menu to ask the food server about their extensive whiskey and scotch choices, was perplexed that ordering a Knob Creek Manhattan was something the new bartender had never heard of. Even had to explain to the food server that Knob Creek was a bourbon to use in the Manhattan, not that a Knob Creek Manhattan was some "type" of Manhattan. Oh well. I guess that's what you should expect when most of their signature cocktails feature Deep Eddy vodka. Beyond that, the tuna appetizer was very good and both our entrees hit the spot. Was shocked to see the 2.5 rating on Yelp post dinner, as Google Maps ( which we used to choose dinner) had them at 4.5 stars. read more

Walking through Annapolis and saw Middleton Tavern, we came here because it said established in 1750 so assumed it had to be good for being open that long. Sadly we were a bit disappointed and not sure if they changed the menu but it was super underwhelming. We started with the calamari and it wasn't bad but the sauce it came with just didn't match the atmosphere and wasn't great. I got the tri tip sandwich, and the flavor was decent but the meat was ice cold and the bread was hot so it had a weird overall temp, unsure if that was done on purpose. Fries are not seasoned and ranch is not good. My partner got the Catalina burger and he was a fan of that so maybe I just got the wrong thing. Atmosphere was quirky which I do like but overall was an ok experience. read more

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Unfortunately the food here was incredibly BAD. 0 stars for the food, but 1 star because I feel really bad for the servers who work there :( we ordered fish and chips, oyster shooter and beer. Oyster shooter was ok, but too expensive ($4). Fries were so mooshy, felt like they were 2 day old. Fried fish was also not crispy, fish itself wasn't great either. Cole slaw wasn't fresh at all. The worst part was, we paid $20 for this insensible food. Skip this place spend your money elsewhere read more

Middleton Tavern - Fish and chips - Seafood Near Me - Annapolis, Maryland

Very bland unseasoned food. The place was empty on Friday night. Only 1 meal of the 4 could be recommended.

Eat here at your own risk. 1/2" of dust on everything. Windows are moldy and the bathrooms were worse than a truck stop. Can't imagine what the kitchen looks like. read more

Middleton Tavern - Mold growing in the bathroom adjacent to the kitchen. - Seafood Near Me - Annapolis, Maryland

So good!! The crab cakes were amazing our waiter claimed them to be the best in town. Such a cool place you can tell there's a lot of history. Would defiantly go here again! read more

Middleton Tavern - Crab cake - Seafood Near Me - Annapolis, Maryland

Service was great, food was okay. Lately, DTA restaurants have been severely lacking. My most recent experience with Middleton Tavern was no different. The location is great, and the staff were very accommodating, however, the food was overpriced and "mid". The fried fish tasted obviously frozen, sauces were store bought, and the portions were all small, however the price was not. Maybe visit for the drinks, decor, and history, but skip the food. read more

Ok so a friend recommend it. I believe it has potential to be great. The history is amazing and you can totally see the presidents hanging out here. My wife ordered the caprese salad and the Maryland crab soup. It was just ok. The caprese salad was the best thing we had. I ordered the salmon Oscar it was good but not worth the money. Everything's felt like it had sat on the heater too long. Was disappointed with paying a lot of money for subpar food. Probably won't return to this place. read more

Middleton Tavern - Salmon Oscar - Seafood Near Me - Annapolis, Maryland

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Wonderful service and atmosphere! Accommodated our group of 9 for Happy Hour beautifully. Good menu options and fresh seafood! read more

We came to Annapolis for a day to walk around and grab a bite to eat. Came in on a Friday, and the place was pretty empty. We ordered a burger with fries and steamed mussels. The burger was okay, but the mussels were not. There was very little flavor to the broth. There was a very nice size portion of mussels, but they were just not that tasty so I ended up not eating a lot of them. Our server was okay, although we did have to ask for the check more than once, and the attentiveness should have been better with a very empty restaurant. read more

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Went to the Middletown tavern to have a nice dinner before fireworks last night, which didn't work out to be. The hostess at the tavern was the most rude hostess I have ever encounter. She point blank said there was no tables available and told us there was a a 30 minute wait and didn't even write down any info about our inquiring for a table. She had a very disrespectful attitude and should be formally trained on how to be a hostess at a restaurant when it comes to talking to potential customers. I only reason I gave one star is because I had no choice to be able to post this comment. read more

A historic property that was established as a tavern in 1750. Right across the street from ego alley and docks. We had a variety of food and everyone enjoyed there lunch. My crab cake sandwich was good. The fries are pretty standard and OK. It was a cool damp day and the chili really hit the spot. The staff was really nice and helpful. Our food came out in a reasonable time. There were a few TV's with different football games. read more

My son and his family joined me yesterday for lunch at Middleton Tavern. The food was excellent and our server Kathryn was efficient and very friendly. We will definitely be back and hope to have Kathryn wait on us again. Ray Gordon Bel Air, Md. read more

When I heard about the Middleton Tavern being the oldest bar (established 1750) establishment around, I had to visit for myself. And what a cool place it is. The Tavern was frequented by members of the Continental Congress meeting in the State House on such historic occasions as the resignation of General Washington's commission, December 23, 1783, the ratification of the Treaty of Paris ending the Revolutionary War in January 1784, and the Annapolis Convention which laid the groundwork for the Federal Constitution Convention held the following year in Philadelphia. It was a dreary damp afternoon and only had a few hours, but if I missed this, I would never forgive myself. I wasn't there to eat, just to enjoy an ice cold beer, just as history would have been back in the day. I bellied up to the bar, with only a bartender to greet me. And since I was here for my first time, I had to try a Middleton Oyster Ale. What a delicious ice cold draft beer. I really enjoyed it. After a few pictures of the place and a visit upstairs to see what was up there, I exited to the streets and walked around a little while longer before leaving with a great big grin on my face. Be sure to stop in and let them know I sent you. read more

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Ambiance only thing available was sports bar where we were informed could order pizza and tostie out of lunch hours on phone. Got to pub not packed had few people in there. got to the bar and told him we had call and we knew was out of lunch time. Said no pizza tostie only premade and ham and cheese only. not what we were told 30min prior on phone. Places order for tosite and got rushed to paid on the spot not mention of drinks . We asked if could order drinks so had a second transaction with misable blunt and rude (older bar staff) he was not busy and two other there at the bar helping. With the attuide we collected drinks placed them on the bare area table and walked out to find better service. Highly recommend Goolwa saltwater cafe. Great food service thaks for saving the day. Had a fulltime carer with first outing away from person she was caring for in over twelve months. (there was a carer with her) was a chance at restbite. read more