I came here on a Thursday night after Induction Day at the naval academy. It is in a very convenient location, with so many shops and ice cream shops to walk around and look at in downtown Annapolis. The restaurant itself is fairly spacious and clean, with nice decor. There was live music that started around 8-9pm that provided some nice background music. The service was pretty good, considering we were a large group of 8. They refilled our waters pretty diligently, and the food came out relatively quickly. I ordered a crab stuffed filet, and it was delicious. I also tried my husband's rib eye and it was cooked to the right temperature, and just melted in your mouth. The prices are a little steep, about $30-50 for an entree, so just keep that in mind when choosing to dine here. I would probably go back for a special occasion, otherwise, I would opt for a less expensive dining option in Annapolis. read more

Great divey spot in Annapolis! Ordered the house oysters and some crushes. The oysters were HUGE. The drinks were good and the service was great. read more

Came here with a group of friends on a trip as the original restaurant we wanted was packed. When we were ready I ordered the Popeye muffin (egg, spinach and ham) and a coconut mojito. All I have to say is that the texture of the muffin itself was moist (toasted but somehow still held water residue), and the eggs had no real taste to them. The ham was decently cooked but the saltiness was too over-baring for the rest of the dish. I would compare the food to something you would get at a hotel breakfast. The mojito was pretty good, but definitely not tall enough for the price you pay. In a sense, you might be paying for the atmosphere as their wall decor is really neat and holds a lot of historical context, but it does seem like they squeezed in tables by the entryway to maximize on space that made it seem too cluttered, even for an old-styled restaurant theme. There might be other good dishes on the menu but be wary of the above mentioned read more

It was a cold and windy day for our group's outing. We picked hearty items off the menu such as chili, etc. The food was very good. They have an excellent cocktail and wine list. read more

The Middleton Tavern is like a little piece of history. It is seeming small but has plenty of seating and a bar. The food is fresh, delicious and well-prepared. The lighting is perfect allowing for a nice atmosphere that encourages conversation and dining. The coffee was strong but not bitter; very enjoyable. I plan to dine there again. And the prices and the wait staff were very good. read more

Middleton Tavern - Martha and George Washington - Seafood Near Me - Annapolis, Maryland

Fantastic Bloody Mary with superb homemade pickled veggies. And fireplaces to keep you warm!

Food was TERRIBLE. My family and I visited Annapolis this weekend and we were beyond disappointed by the food at this place. Both salads were sub-par. The Caprese Stack was completely tasteless and only had one piece of basil. I had to drown it in salt to make it edible. The Cesar salad was 98% lettuce. Barely any toppings. Both salads had add-on meat. It was $7 for three "jumbo" shrimp (they were medium at best) and another $7 for a tablespoon of crab on the other. The sandwiches and fries were rated a B. I gave an extra star because the service was great. Otherwise this was a one-star experience. Save your money! read more

This place has a weird odor. Ugh. Came here for Father's Day brunch because everyone else was packed. Thought, "why not?" Now I see why. The food was meh at best and it feels really old in here. The restroom was dirty with graffiti and standing water everywhere. The food was just ok, better than fast food but not worth a return trip. Oh, and the confederate memorabilia? Really disappointing. This place needs a serious upgrade. read more

Middleton Tavern - Seafood Near Me - Annapolis, Maryland

I will NEVER go to Middleton's again! They changed the amount of a tip on a check AFTER the people had left AND had signed it! The waitress had HAND WRITTEN her tip (incorrectly!) onto the split checks. She incorrectly put the tip amount onto one of the checks and by the time she realized it, the couple had already left with the amount SHE had put on the tab. She then went to change it and I told her and HER MANAGER that she could NOT change a tip AFTER the person had left and she did not have consent of the card holders. (I even took a picture of the tab so we knew how much it was originally) She did it ANYWAY and they were charged on their check the HIGHER AMOUNT!!!! Check your tabs if you go here!!!! read more

Middleton Tavern - Waitress changing TIP and total without Card Holders Consent - Seafood Near Me - Annapolis, Maryland

Have to stop in every time while in Annapolis. This place has been here since the 1700's. The bar is the preference to start the evening. A little happy hour and some keno. The staff is always friendly. The food can be hit or mis depending on what you order. Crab cakes and crab cake sliders are excellent. The Bloody Mary was a meal in itself. Pickles, green beans, bell peppers, olives and limes even before you start. My favorite is shrimp shooters! Yep, shrimp instead of oysters with a light beer chaser. They are served in very small cups, separated and delish! This is s must stop for going downtown. Enjoy! read more

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My husband and I ate here for dinner. The food was good and thr service was excellent. Daniel was our server who was great, very friendly and attentive. read more

AMAZING! I had a dang out of body experience w the oyster shooters here! I decided to bust out of my "bachelor" existence and see the rest of the world..and found it here. Don't dare go to Annapolis w/o at least one shooter! This was my first time to this beautiful place, walking around is almost an art here, like San Francisci, having come here 6 months ago, unlike Rockville, which is more like a gulag, than this lovely town. I'm so amazed I'm looking at property already! read more

Worst eggs Benedict. Tangy. Uncooked home fries. Hostess puts us in corner next to garbage and never said we can sit off porch and have more room. Saw I had my grandson never gave a kids menu and crayons, all the other kids had them. read more

This place is a total tourist trip but I can't stay away. I love my free oyster shooter with Yelp check in and I like that it comes with a shot beer back. There's oysters aplenty and their huge. I've also had the crab cake and the lobster sandwich on visits. I've never sat anywhere but the raw bar which is always packed, but there's ample dining room seating. While the decorations are old fashioned and on point, I just don't think I would enjoy the quiet ambiance as much as the faster pace of the bar. I'm also a big fan of the place's proximity to the water and city center and that there's always a seat. I'll keep returning, but I never expected five star dining. Just convenient drinks and oysters. read more

Middleton Tavern - Oysters and Cosmo - Seafood Near Me - Annapolis, Maryland

Service left me waiting... food left me wondering. So we went for lunch... and were hopeful this place would do the trick, it's always busy... I got a Salad that was supposed to have Macadamia nuts and feta with a mango lime sauce. Yeah.. umm.. ok, they gave me some mixed greens on a plate with 1 and a half macadamia nuts... I checked the whole plate... yeah... then the cheese was scant at best... I didn't finish my salad. It was just sooo DISSAPPOINTING. The waitress was like.. oh.. can I take that away and I just let her cause I was in a rush.. she didn't even ask why I didn't eat more than 20% of my meal... knowing I was probably still hungry. Now Neil fared a bit better with a deli sandwich with chips... not very memorable cuz as I am asking him right now, he can't remember. The check was $26... too much for a half arsed salad and small sandwich. Did I tell you when we walked in the host just told us go ahead in if you want to sit inside.. he sounded offended we didn't want to sit inside. It was a big dank,dark and small roomed inside... I liked that coziness, but not if the food and service is going to stink. Great location, but there are better places to spend your dough. read more

They say George Washington drank here. We came here for the history, to say we drank where the great men of our history drank. We got that experience, but it wasn't what we hoped. It opened in the 1700's and I'm not sure the place has been updated much since then. Overall the experience just felt disorganized. There were typos on the menu, and the waitress was not very friendly either. The music was awful and the in-ceiling speakers are in major need of replacing. The food was decent, but basic. Just not the experience we had hoped for. We weren't really sure what to hope for, but what we got wasn't it. It's cool to say we've been here, but with so many great choices in downtown Annapolis, I'm pretty sure we won't be back. read more

Came here with my best friend who so happens to be a very picky eater. After walking around the circle on Main Street and walking in and directly out of Market Place, we decided to sit down outside here at Middleton Tavern. The patio was welcoming and the view was great. We love to people watch and look at the ridiculous outfits that Main Street has to offer on such a hot day--we even saw two girls just walking around in bathing suits?! Anyways... We LOVE love LOVE oysters so of course we decided on getting 1/2 dozen to share. The platter came out with two very large oysters and the rest so small in comparison! My friend wanted to complain, but I honestl7y wasn't in the mood to deal with managers on a day that already started off awful. I ordered the Soft Crab BLT with no Mayo and she ordered the Flatbread. Our food was GREAT! We even ordered a glass of wine each and used our Yelp log-in check-in FREE oyster shooter. THE SHOOTERS ARE THE BEST! They come with TWO oysters in the shot with a baby shot of NattyBoh beer. Perfect lunch. Bathrooms do need some updating and maybe some more signs? There were a lot of drunk people (even at 2:30pm) that had NO idea where the bathrooms were and kept asking us...we were outside!! read more

Middleton Tavern - Oyster shooters! - Seafood Near Me - Annapolis, Maryland

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A wonderful traditional colonial pub and restaurant. The bar at the side has Great character and the food is fresh and nicely prepared. I especially recommend the muscles,the best in town. read more

2.5 stars is generous. We waited 25 minutes at our table with no acknowledgment. It was if we were invisible. It wasn't even that they were busy, but we waited patiently for awhile before heading down the street. read more

As I can't find my review from the other day, decided to repost. Food was ok until a lady screamed and kicked a live roach off her leg while dining. Roach was in middle of floor after that holding onto food. Manager was alerted and retreated without apology to the whole room stating, " I can promise you that I spray weekly, but still have a problem in one area." Go elsewhere, I saw a review from 2019 showing a picture of a roach, so it's been infested for some time. Reported to Annapolis health department on 7/4/2023 from our visit on 7/3/23 read more

Not the worst restaurant ever, but we definitely won't be going back. I ordered the mussels, and half of them were closed. The open ones were cold. When I mentioned how many were closed, our server said they were "supposed to be that way" and told me to just pry them open. I'm no mussel expert, so I ate 4 raw mussels before my friends told me they weren't supposed to be that way. My friend ordered a burger with cheddar, and received blue cheese. She scraped it off, while the server watched, and then a different server offered to take the blue cheese covered burger to the back to melt a piece of cheddar on it. It still tasted like blue cheese. I've worked in several restaurants, and I can say I've never been allowed to take a burger back to the kitchen and place cheese on it and bring it back to the table. My other friend's burger came out 20 minutes after everyone else's food, and was cold because the server left it sitting back there. While I was eating, a server let a dirty napkin fall into my food from the bus tub and did not offer to replace it. For how much money we spent, I couldn't believe how bad the experience was. We tipped 20% because I'm a server myself and some things weren't her fault, but I'd never recommend this place to anyone else. Also, another server refilled our water for us before we left because our server never noticed the empty cups. read more

Not sure what is up with all the bad reviews...This place is an institution! It's old and creaky and quite possibly haunted. The hot crab dip, crab/lobster bisque and crab cake are on point. It's a bit dusty and dark but you can't beat the location and the feeling that you are surrounded by history. Our server was quick and friendly. Food was hit and flavirful, the seafood Cesar looked awesome and our kids all enjoyed their burgers. Also right now if you check in on Yelp you get a free oyster shooter (shot of beer with a raw oyster in cocktail sauce.) read more

Middleton Tavern - Seafood Near Me - Annapolis, Maryland

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This historic tavern from 1750 has such fun atmosphere to enjoy a nice meal in (especially if you like brick fireplaces). My family and I went here for dinner and although the prices were on the high side, we all had really nice meals. They have a huge menu with lots of different seafood, steak, chicken, pasta, and salad options, as well as a la carte sides that are good size portions. I ordered the baby lettuce salad with grilled chicken and a sweet potato on the side and I left there very satisfied! read more

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I rarely leave poor reviews but was so disappointed in my experience at this establishment I feel obligated to share. We arrived close to nine and were approached by someone outside asking if we'd like to eat at the restaurant because the restaurant we were planning on going to already closed. He told us they were serving until 10 and we decided to eat inside because it was cold. As he walked us in the server looked at us with straight irritation. (Later we find out they were supposed to stop serving at nine which explains why everyone was cleaning around us and not excited to see us). We look at the menu and decided to eat as fast and inexpensive as possible so we could leave. After sitting down for one minute the waitress comes over and asked if we know what we'd like, she never gave us any specials or advice. Saying we need a little more time she walked away irritated. Five minutes later we ordered lobster soup, bagel pizza with fries hot wings and naked wings. The woman who brought our food out was the first person since sitting down that was friendly which was a breath of fresh air. The lobster soup was lukewarm and so so so rich I couldn't eat it. The fries and hot wings were barely cooked and just looked disgusting. The best thing was the bagel pizza my granddaughter had and that was nothing to write home about either. I am so thankful we didn't go in there and order a nice entrée or I would have been thoroughly livid with that type of service and quality of food. Towards the last 15 minutes of our meal the waitress finally smiles and actually show some concern or interest in us. Another thing I find quite odd is the menu is quite pricey but the whole staff is in shorts and T-shirts without anyone even acknowledging or saying hello to us. One of the main parts of eating out is having a great experience and this one failed miserably read more

We sat outside and had great service!! Food was decent and had a good vantage point for people watching. Would def go back just for the great service and people watching. read more

Never let someone who can't cook choose the restaurant. Yes the mussels came in an impressive heap, because the mussel flesh was the size of a fingertip! The seafood salad was a disappointing ripoff, two small scallops, two shrimp which tasted of chlorine and were inedible, and a scant tablespoon of crab meat. The bread was gummy dinner rolls. Glad I did not order an entree! Sign me Tourist, Trapped. read more

First visit was during USNA's Parent's Weekend in 1981; my plebe summer friend was from Maryland and they knew about this restaurant. Most recent trip was yesterday and the food is absolutely awesome. Fresh oysters, crab meat, mussels, crab balls, steamed shrimp, man did we eat like a school of sharks! We were in the bar because that was where the action was happening. Live band, people dancing, our group mowwing it down, beer flowing and life was good! Bartenders were efficient but over-extended I think. They were serving drinks AND food to a full bar of people and it was a handful. So, we had to wait a few minutes, no big deal. We were ordering 2 or 3 things off the menu, eating it, and then deciding the food was great and ordering more. Saw some midshipmen there but it also looks like plenty of locals also like this joint. read more

There was a long wait at the Iron Rooster, so we ended up coming here. Their menu is sort of pricey and they don't have many vegetarian options. I ended up getting the penne pasta with vodka sauce and fries on the side since I really wanted fries. Their fries have skin on them, which I don't like, so it was just okay. The pasta was really good but I still don't think it should be $16. My boyfriend just got a regular burger because it's hard to go wrong with a burger, but he said it was terrible and he couldn't finish it. The meat tasted like it was microwaved. For the price and quality of food, we won't be back here. read more

Middleton Tavern - Penne vodka! So good! Fries were ehh though. - Seafood Near Me - Annapolis, Maryland

Delicious mussels in a white wine garlic sauce with onions, tomatoes and perhaps a touch of Old Bay. Outstanding lobster-crab bisque with fresh baked bread. Cosmos and cocktails a thumbs up. Friendly service. Super romantic quaint old Colonial atmosphere. A nice option on the Annapolis waterfront. read more

Middleton Tavern - Cozy up by the fire in this historic pub on the charming Annapolis waterfront. - Seafood Near Me - Annapolis, Maryland

Barely average. Food, service and drinks are all forgettable. The high spot was the crab cake. Very flavorful and with a good sauce. The beer selection is poor so we chose mixed drinks that were way too sweet. The servers gave the impression they didn't want to be there. There are much better choices in the area read more

Came here and sat at the bar to get some oysters and drinks. It is almost like a dive bar and their beer selection isn't that great. The oysters at $2 a pop were not that great and were from North Carolina. I was confused as I was in Annapolis, Maryland and was wondering why they didn't have oysters from closer by. Who knows. Anyways I got an orange crush mixed drink too which was very good. The bartender was nice and personable; there is also keno here and we won! Over all it is an ok place to stop for a drink mid-day but it is nothing special and I would expect more from a place close to the water in Annapolis. read more

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

Host was super unkind but their bartender was very kind and friendly. They have good foods and drinks!

the main bar tender could not be more rude I tipped him 25% on one drink and he said.. and I quote " THANK YOU SO MUCH 2$ now I can retire." super dirty and obnoxious staff horrible place... there are so many restaurants and bar I recommend you go anywhere but here read more

1 star for ambiance, 3.5 stars for food, 4 stars for service Ambiance feels like you're at your best friend's grandma's house. The building is extremely old and smells old too. Decor is random, including heads and bodies of hunted animals and old china. Food was pretty good, especially the veal pasta entree and Alfredo pasta. Steamed mussels were also very yummy. The seafood Caesar salad, tomato & cheese dish, sirloin burger and prime burger were decent but nothing to fight over. The oyster shooters are cheap ($2.25/shot) and delicious!!! Make sure you get a round of these for everyone in your party! Our 2nd bottle of wine that we ordered while eating appetizers came out after we finished our entrees. The server explained that a part of the cork broke and went in the bottle. The bartender had to filter the cork particles out of the wine so it took a long time for him to bring it out to us. However, we still found cork in some of our glasses. The wine tasted fine and they gave us a 30% discount on the bottle for bringing it out late so we didn't complain, but I expected better at a restaurant that runs around $40 per person. read more

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

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Amazing food experience!!! You will not be disappointed at all. We had three appetizers: crab balls, calamari, oysters rockefeller. All were beyond belief. Being from Louisiana these dishes were superb with the distinctive flavors. The oysters Rockefeller was the best I have ever had, gave me goosebumps. The crab dip was mind blowing, each bite making you crave more and more. Then came the main course, the salmon Oscar! A literal tear formed in the corner of right eye as the flavors exploded in my mouth. It was beyond, again anything I had experienced, cause taste is not sufficient enough to describe this. You must at least let these amazing dishes enrich your lives. We had the amazing pleasure of dinning with the executive chef, tyvm Mr. Authur, for making this a life changing experience as well, as a time I will never forget. I look forward to your visit to the great state of Louisiana, as you are now and forever family! read more

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

This is a good place for out-of-town visitors to get an OK meal. The atmosphere is nice, the service is good, and the food is acceptable. We shared a mussels appetizer. The mussels were small but clean in a flavorful broth. Even though we asked for extra bread, it came with two tiny bits of stale toast. I had to return my order of fried oysters because they were full of shell pieces. The house gave me crab balls that were quite good. There was a Yelp offer for an oyster shooter that I loved. The oyster was clean and complimented by the house-made cocktail sauce served with a beer shooter. read more

Not sure why this place has low reviews! We enjoyed our oyster shooters and crab cake sandwiches. I would have preferred a better bun for the crabcakes (sesame bun for seafood? Seems store bought) . Also fries weren't evenly proportioned, my friend got a healing place and I had 10 at most on my plate. Service was great though! Good place for casual lunch outside. read more

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I felt kind of bad giving two stars, but Yelp's description of "Meh. I've experienced better." was just the exact descriptor of my experience. I did eat here outside during the pandemic and despite restaurants just beginning to reopen, service went quite well! However, the food was nothing at all to call home about. I had the burger and my parents the crab cake and the crab cake sandwich. Everything seemed pretty sub-par like we could make at home. I do like the outdoor seating and ambiance! read more

Ok, not sure why this place has low stars...the food was AMAZING and our waitress was super helpful with navigating some dietary restrictions. Awesome atmosphere and again, food was incredible. Will be coming back! read more

The Middleton Tavern is perfectly okay on a random Saturday night in June. Trying to manage expectations here - after all, you can only get so many stars when draught beers (Blue Point Toasted Lagers) are served in clear Dixie cups. Pretty crowded night around town, but we were able to walk up and grab a table on the front deck. Beers (decent draught selection and the typical domestics), oysters (DE River variety), peel-and-eat shrimp, Maryland crab soup and Maryland crab cakes on fried green tomatoes - pretty good. Service was a bit touch and go, but server was doing the best she could with a great disposition, given the room she had to work with. Deck was pretty tight. We'd definitely stop in again. read more