Hot and sticky...inside. Â Forget eating outside, too hot. Â The interior has a 70's feel to it. Â Nothing updated since the disco days. Â Maybe not wiped down either. The absolutely most annoying thing was the kitchen door slamming every 5 seconds, no lie. Â If you sit in the main dining room, the swinging kitchen door is right there and slams every time the use it. Hello, is it obvious that could be a problem??? Â Felt sorry for the people right next to it. Â The service seemed ok, the food was ok, it's just the "Inn" doesn't feel like an Inn, but like an old worn out restaurant. Â A make over would help.
Review Source:Awful.  This place needs a restaurant makeover from stem to stern. Badly. When I asked our waitress for an ale, and she had only one to offer that doesn't appeal to me, I asked about other beers.  I'd asked for too much.  To shut me up she then offered to go through a lot of trouble, basically threatened, to read me a list of beers....not.very.helpful. Should have left then but stupidly ordered the crappy ale they serve..  Actually, we should have left after walking in and smelling the foul stench of something that had gone bad someplace in the house.  The 'surf and turf' sandwich I ordered was not good.... I didn't see or taste any evidence of  'turf' in the glob of slaw slabbered onto the bun, whereas the surf appeared to be a couple of small, overcooked shrimp rather than the scallops promised in the menu.  The french fries that came with the dish were several hours old. First time in my life I've ever seen someone screw up fries.  My dining partner had a burger, and he was not at all impressed with it.  No evidence of the "blend of 4 grounded prime cuts" or "herb mixture" promised in the menu.  Neither of us could finish the meals, and we usually lick the plates clean.  You might ask, "Why did you put up with this?  Why not say something?"  The answer is simple: It was a long day, we were tired, thirsty and hungry..and we had an invisible waitress, .  Not really sure where she disappeared to, because most of the other staff were in the bar area where we were seated...chatting with each other, or watching the Orioles baseball game on the tv's (NTTAWWT).  Can affirm these other reviews and only wish I had consulted Yelp prior to going over there, the service was slow and inattentive...the food overpriced and of truly poor quality (seriously? you'd serve fries that have obviously been sitting around for hours??? seriously?? ...just a bunch of slopped together crap..  All in all, just a horrible restaurant in a great location.  It really really needs a makeover.  But I'm so pissed, even if it got one, I'd never return.  The only reason I left a small tip is that the waitress never came by to pick up the payment and I didn't have exact change for the meal.  Wish I could give less than one star....or a negative star.  Or better, an anti-star that annihilates stars given by other reviewers.  O.M.G.!!
Review Source:Along with what feels like a million other people in Annapolis for the 4th, my friend and I wanted to get some good seafood by the water! Â So we stopped into Middleton Tavern. Â With the looks of the place and the look of the menu, I figured it wouldn't be too expensive. Â Then we sat down and actually read the menu. Everything was over my budget to begin with, but then I figured I might as well allow myself to splurge for the 4th. Â I have a thing for filet oscar, and get it whenever I can, so I decided to go for that! Â
It's the most I've personally spent for a meal in well over a year (others have spent more on me, but this was out of my own pocket...). Â
The filet oscar came with asparagus and mashed potatoes, which both LOOKED fantastic. Â The asparagus was perfectly cooked, actually. Â The mashed potatoes...didn't taste like anything. Â They might have been from a can...seriously. Â The filet tenderloins were okay, but absolutely nothing to rate over 2 stars. Â I have zero skills with cooking steak, but I could've cooked those like that. Â At medium well, they were a little pinker than they should've been, but I didn't feel like sending it back. Â The crab chunks barely even tasted like crab. Â I can't describe that effectively...if I had been blindfolded, I wouldn't have know that it was crab. Â It just didn't have any taste. Â The bernaise sauce that was supposed served with it...well, I couldn't identify it. Â Could I have asked about that? Â Sure. Â For the amount of money I was paying for the meal, should I have to? Â Nope.
At $32 plus tax and tip...SO NOT WORTH IT. Â *Service was good, so I still tipped well.*
Sorry, Middleton. Â I would not only not come there again, but I would not recommend it to anyone either. Â I would suggest that you get some real recipes for that particular entree.
She said..." Tried to find a cute place in Annapolis to eat for my moms birthday, however, we picked the wrong place! Looks cute from the outside, but I am sure there is much cuter and tastier places in the area. The decor was very old and dirty looking. The service was not great and the food was not something worth coming back for."
He said..."Eh... Â $10.95 for a $4 burger...sorry not for me, I'll go to Hardee's for a better burger next time."
An out-of-town couple who are friends of mine were coming to Annapolis to celebrate on of their birthdays. Â They asked me, a local, to recommend a place near City Dock that would represent Annapolis. Â Although I had not been there before, I suggested City Dock. Â I would join them for dinner.
When we got there, I recommended that we sit outside. Â It was a beautiful night in Annapolis and we had a great view of the City Dock area. Â
Our service throughout the experience I am going to tell you was fair. Â Not great, but fair.
I ordered crab dip appetizer and my friends order shrimp martinis. Â The crab dip was good, but it came with store bought crackers, not toast points like you would find elsewhere in Annapolis. Â Their shrimp martinis had two shrimp each. Â There were more just glasses of ice.
Two of us ordered the filet with crab. Â Not cheap. Â But it was a birthday dinner.
Both filets came out gray. Â They weren't grilled. Â They were reheated, microwaved or possibly boiled. Â The crab on top was good. Â The broccoli on the side was cold, as if they grabbed it off of a veggie plate. Â
I decided that I would try to eat it at least. Â My friend sent his back and ordered a cheeseburger. Â His cheeseburger came out and was something that had been reheated, bun and all, in a microwave. Â By this point, I gave up trying to eat my steak and decided to take it home to my dogs. Â
The manager came over. Â He was insincere to say the least, until I stated that I lived in Annapolis, recommended this place, and was VERY embarrassed. Â He took a large portion off the check. Â I was still mortified that of all the good eating places in Annapolis, I had recommended this place to out of town guests.
The manager took a large portion of the meals off the check, which was good. Â But I will not go back there again. Â The food is subpar to airline food or a high-school cafeteria.
Huh...I thought it would be a lot better for the price. The oyster shooters were amazing and I loved my grapefruit crush. For food, I ordered the Maryland crab soup and the seafood tower for two as an entree. The soup was yummy with big chunks of crab, but the portion size was small. The seafood tower was very so-so. The seafood did not taste very fresh like I expected. The calamari was not warm and even a bit soggy. It was overall okay, but I expected better. The service was fabulous, though.
Review Source:A historic property near the city dock in Old Town Annapolis, that works well in summer (you can take advantage of the covered terrace) and in winter when it feels suitably snug.
The property has a homely feel to it, and service has always been good when I've been there. Â Menu is mainly seafood focused, and on high side of mid-price, which is to be expected given the location.
Live music some nights.
Neat place near the waterfront. Lotta cool kitsch on the walls, and the locals are really friendly and eager to talk. Dinner was good, but we enjoyed coming back the next morning for an unofficial brunch of oysters rockefeller, crab cake sandwiches, and oyster shooters. Didn't get a chance to check out the piano bar upstairs, but I hear it's great. Will definitely come back whenever I return to Annapolis.
Review Source:The only good thing about this place was the location. Â We waited over an hour for very bad food when it wasn't even busy or crowded. Â The service was just horrible. Â Â We were sat next to an open service area and watched as they dumped food into garbage cans. Â Super disappointing.
Review Source:My mother-in-law was in town on Saturday for the day and she wanted to eat in Annapolis. After some shopping we went into the Middleton Tavern. It was about 11:30 and the restaurant was not even half full.
We were greeted by our waitress and she told us that it was her first day on the floor by herself. I was concerned but she quickly put my mind at ease when the drink order came right out.
Now there are three of us and we ordered a total of four dishes
1. One dozen oysters with champagne mignonette
2. American chopped salad
3. Blackened Mahi-Mahi with vegetables
4. Chicken Melt sandwich
The oysters came out right away with a side of cocktail sauce. No big deal. So I asked for the champagne mignonette and she told me that it was already on the oysters. I knew that this wasn't true so I picked up one and showed her that there was nothing on the oyster. She went back to check with the kitchen and came out with the sauce. There was an apology but it wasn't necessary because she is still learning the job. I tried the sauce one one oyster and it was terrible. A champagne mignonette is supposed to be made with champagne vinegar not red wine vinegar. So I finished the oysters with cocktail sauce. The oysters were small but fresh. They didn't have a lot of taste or finish but I'm not sure if the time of the year is right to get full flavor from an oyster. That is probably my mistake for ordering oysters to early in the year.
Now everything comes to a grinding halt. We watched people get seated but no one was getting served. After about 25 minutes the tables around us were getting their meals. During this time our waitress checked on us twice and brought us more drinks. She said that our food should be coming out soon. After 35 minutes we were served our meal. I had the salad so there isn't much you can say about a salad except it was what I expected. My wife enjoyed her fish and the mother-in-law thought the chicken was just ok.
Once we ate and asked for the check our waitress disappeared for 10 minutes. She finally brought the check and I kept her at the table while I quickly reviewed the bill and gave her my credit card. She came back rather quickly and thanked us.
I understand that the waitress was just starting out so there is no issue there. There isn't an excuse for the kitchen taking 35 minutes to make our meals when the restaurant is less than half full. You can get this type of food at plenty of other restaurants in Annapolis so the Middleton Tavern is not worth your time
Overall the experience was -- Meh....
Price - Seemed a little high for the portion size
Atmosphere - It has the look and feel of a waterside restaurant that needs the walls scrubbed clean
Noise - Fairly noisy
Staff - Courteous and friendly
After a long day of site seeing, my husband and I stopped in here for a drink and a small bite. Â
We ordered the calamari and the oysters...both were excellent. Â Probably the best calamari I had in a long time. Â
After a lousy dinner that evening at another restaurant, we wished we would have returned to Middleton Tavern for dinner.
Oh and the music was great. Â
The singer was Angie Miller. Â Wish we had stayed longer to listen to her.
So the place is an Annapolis staple for sure. But why does this place continue to be soooo expensive for the same seafood that all the other restaurants in downtown serve too? Makes me think they gouge tourists. Oysters Rockefeller, clams casino, steamed shrimp ($20 for 1/2 pound of u-40 size??) come on annapolitans, it may be time to stop going here until they get it together. $30 for a 6oz piece of grouper and a sad dish of green beans? The prices are ridiculous. snow crab legs were ridiculously priced and could fit on a 7 inch plate. I'm boycotting. The tourists will keep the legend in business but I will go elsewhere
Review Source:Allegedly, George Washington had his after party here upon resigning his commission. I sat at a table in the bar, ordered up calamari and crab dip and had a local brew. The service was great. The food was OK. The place didn't look all that old considering the history. On a stroll through quaint Annapolis, this isn't a bad stop at all.
Review Source:This is a fun place at the end of Main Street, right on the water. Â It's an old bar turned into a restaurant. Â It's neat to think about the people who may have sat where you are sitting through out the years. Â The food is okay, but this place is really about location. Â Reasonably priced bar food and quick service.
Review Source:It's an old pub, a piece of history in this navy town. Food is eh, service is delightful. Â But the banana chocolate chip cake is moist, decadent and oh so wonderful! Â I don't do pubs, so I went because the class folk went to reminisce about their glory days. Â Great wine list for a pub. Did I mention the chocolate chip banana cake!? Â OMG! Â Maryland crab soup was, eh, oysters were warm and bland, the crab sliders were decent. Â But that cake?!
Review Source:Decent seafood food. Â We had the New England clam chowder (pretty good), oysters sellman (don't think oysters are meant for bacon and cheese), beet salad (excellent! covered with feta and pistachio crusted goat cheese), crab sliders (also excellent, the cole slaw is great and it doesn't need the tartar sauce), crab middleton (good, but the side of rice and veggies are bland), and fish & chips (heavy breading on the fish). Â
I like that you can sit outside at this one (more places need outdoor seating).
Over the past 2 years I've come to like Middleton Tavern. First time we attempted to eat there was right after we moved to Annapolis and, unbeknownst to us, it was parents' weekend at the Academy. We tried to get a table for lunch and the place was just jammed. After killing over an hour at the bar waiting for a table, we left.
Fast forward to spring 2012. My cousin blows into town, haven't seen him in years, he wants to have lunch in historic Annapolis so I suggest Middleton seeing as how it's near the stuff he wanted to see and likely not too busy on a random Wednesday at 11am.
Turned out to be a really good decision. We were a party of 6 and tried everything from appetizers to soup to salads, burgers, sandwiches, and pasta. Everyone was thrilled with their food and the service was good. I had a cheeseburger that was one of the best I ever had.
A month later I was downtown with a friend and she wanted lunch. Specifically a burger at Middleton so we ate there on a busy Saturday and had pretty good service. The food was good and hot. We sat outside on this occasion which was a little cramped but nice for people watching. Who wants to be stuck inside (it's pretty dark in there) on a Saturday in June?
Glad I gave them another few chances. I'll be back.
Very, very mediocre and below average.
The first thing you may notice as soon as you enter the restaurant is how bad it smells. You know when a cleaning rag/towel hasn't been cleaned in awhile or when you forget about your wet clothes in the washer? It smells like that.
The service was fine. The food was very below average. I mean, it was fine but I was like ...... are you serious? I had heard good things about this place but it was like... uhhh.. those are the skinnest and wimpiest asparagus sticks I'd ever seen served to me in a restaurant.
The butter that came with the rolls tasted really funny. I really like bread and butter, but the butter tasted funky and sour. It was yuck.
The oysters were very meh as well.
Waste of money.
Great food, seemed like great classic rock atmosphere if that's your thing.
The downside for me was that we came for the food and the band was very loud and was a few decades behind our taste. Â We also arrived at 10:00 pm on a Saturday hoping for food, but the waiter rushed us because the kitchen was closing. Â I don't think you should seat customers if you don't have enough time for them to order. Â I'll certainly come back for those crab cakes, but I'll make sure to avoid nights when they have live music.
Yeah, so...this place is a kind of institution. It has a primo location. Atmosphere: is kind of like your college dive bar and historic inn had a baby. I managed to live in Annapolis for two years without eating here. That changed seven years from that time when the place I really wanted to go for crab cakes was closed. If I hadn't been starving, I would have kept going. My food was just okay...and kind of expensive relative to quality. The fries tasted as if they were made days before. I wasn't surprised by this, but you should know. Service was just okay. In a word: mediocre.
Review Source:Came here and sat at the bar to get some oysters and drinks. Â It is almost like a dive bar and their beer selection isn't that great. Â The oysters at $2 a pop were not that great and were from North Carolina. Â I was confused as I was in Annapolis, Maryland and was wondering why they didn't have oysters from closer by. Â Who knows.
Anyways I got an orange crush mixed drink too which was very good. Â The bartender was nice and personable; there is also keno here and we won! Â
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.
It was okay.
I didn't love it.
We were seated right away for lunch on Friday, which I know was lucky because it seemed like every table inside and out was packed.
Our server was very pleasant, a little space cadet-y though. Â I asked for an extra glass of water (I'm 9 months pregnant and they had those little glasses of water on the table) and she assured me they'd be by to fill me up frequently. Â Literally never got a glass of water after my first two gulps finished my glass. Â
Flagged her down for another diet coke, she went about her business and had to ask her again 10 minutes later after she shot the breeze with another table.
Pregnant ladies get thirsty!!
Prices - pretty steep, but you're absolutely paying for the location. Â A burger went for $9.50 if you got cheese, it was cooked well, not a huge burger, and you got about 17 fries. Â All of it was REALLY tasty, just a little small for the price. Â Husband got the oyster po boy and enjoyed it, Mom got the crab cake sandwich which was ominously listed as "market price" -
For three moderately priced sandwiches, and a beer...lunch was $55. Â So there you go. Â If we had been able to snag a table outside, I probably would have just shut up, but inside is a little dark, server is medium (in competency, not demeanor), and the bathrooms are all the way upstairs and gross!
The manager (or perhaps he was the owner?) was super friendly, as was everyone else. Â I won't be running back, but I'm not harboring any ill will towards Middleton.
Everything here is very very delicious, however the prices are a bit too high for what it is. This is your typical downtown Annapolis establishment. Indoor historic building with some outside seating, luckily the outside seating has a roof to shield from sun.
Went here on a Friday evening for dinner and was treated with excellent service and politeness. Requested a quiet table and they opened the second dining room for me.
I had the burger and my girlfriend had the steak sandwich. The burger was good, albeit small for 9 dollars. Her sandwich was closer to $16 I believe. These were essentially the two cheapest items on the menu.
We did order an appetizer and got the calamari. It was fried as most places are but it had some amazing semisweet, semi-spicy sauces on it that probably doubled the calories but were fantastic in taste! We both loved it and it survived about 5 minutes!
Overall, a nice place but over priced compared to some other places downtown. However, the quality and selections are probably a bit better so you are left with that trade off of "slightly better food with much higher prices or cheaper and almost as good." guess it depends on your wallet!
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.
Ho, hum.
My family and I visited this place after being on the water all day. We did not have high expectations. I was in search of a seafood place where I could get a decent fish or chicken sandwich with a basket of fries. My cousin wanted pasta for the kids. We were not looking for anything exotic, just some decent food. After briefly scouring the options, we settled on Middleton Tavern. But, in retrospect, we should have walked on.
This is just for our bar experience: downstairs seemed a little smelly like dirty people but maybe that's because everyone had been eating seafood there all day and it was hot hot day.
If you head upstairs you will find a piano bar every Friday and Saturday night- we caught a guy named Lawn (can't remember his first name). Entertaining and sang to our girlfriend who is visiting and in town for her birthday. Fun times in this cute little space. We weren't quite ready to leave when the music stopped and when I asked one of the guys working there if he would take a picture of us he said no, he just wanted us to move downstairs. uh. okay party pooper, we'll just go home.
What a charming and cozy place, fireplaces cranking, friendly staff, and nice fellow patrons. Â
We walked by this place on Thanksgiving about 5-10 minutes before they opened and there was a crowd of 20-30 people waiting to be let in. Â Only a few places in Annapolis were open on the holiday and we planned on hitting Middleton in advance. Â
After taking a walk around the docks and down to the water's edge we headed back to warm up and grab a quick drink before heading back to DC. Â When we arrived there was barely one seat at the bar. Â We sat next to an amazing and charming older couple from Ohio celebrating their anniversary, on one of their many trips to Annapolis every year. Â
They were having oyster shooters, an oyster swimming in cocktail sauce, accompanied by a similar sized dixie cup of beer. Â They looked pretty good, so we ended up having 8 of them. Â
The staff was quick and attentive, also incredibly friendly, when we got the bill it was seriously like $12 for both of us, ridiculous. Â Apparently this place has gone through a couple owners and looks throughout the years but this current incarnation really captures the feel that this was once a sailor's hangout with an amazing history including patrons like Washington, Franklin, and Jefferson drinking by the fire hundreds of years ago. Â
Well worth a visit if ever in Annapolis.
It seems really silly to go get oysters after a night of drinking at a wedding, but that's what we did. My friends had oyster shots and I had half a dozen of the house oysters.
The oyster shots were good because the beer came on the side in a little cup so you didn't have to chug the oyster in the beer. That made them more appealing to me. I once tried to shotgun an oyster shot that was vodka + oyster and almost ralphed all over the patrons.
The oysters themselves were good, but I had better. They were definitely large, but just a tad bit gritty so I would pull out little parts of the shell in my mouth. I'm not sure what variety they have and for a place with Oyster Bar in the name you would think that they would let you know what the house oysters were. And they only had one other kind on the menu labeled "specialty oysters" again, not sure what variety they were.
The serving sizes of other things were not very large, and for that price and taste--eh. The Maryland crab soup was hearty and delicious though, as was the chili that came with 8 thousand things to add to it like cheese, diced onions, etc. So that was nice.
I'd try another seafood place on the dock... one of them has bound to be way way awesome all around for that price and location.
Disclaimer: Â This is a completely biased review. Â I've never eaten at Middleton's, however I have enjoyed some beer there that was pretty tasty.
What I can tell you is that my former neighbor, Larry Lay, plays piano and sings there and he is crazy talented! Â Go, Larry! Â If you happen to see him, give him a shout out from his old neighbors Kristy and Alan!
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. Â 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. Â It was just sooo DISSAPPOINTING. Â 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. Â 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. Â 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.
Narrow doorways and stairways. Â Cramped rooms, hot upstairs in the summertime. Â This describes Middleton Tavern pretty accurately, but before you stop reading let me explain why. Â A tavern built in 1750 on the waterfront (Chesapeake Bay) is probably not going to offer the conveniences of a modern day bar. Â What it does offer is a glimpse of the way taverns used to be, meaning back even before our founding fathers freed us from the binds of Britain. Â Go to Middleton Tavern just to step back in time and enjoy this time machine for what it is, possibly the oldest tavern in America. Â
 Oh, and the food is pretty damned good as well.  The oysters are fresh, as would be expected, and served the only way they should be: raw on the half shell or as a shooter.  You can also find raw clams at the raw bar, or a bucket of steamers.  Seafood is their main forte, but Middleton also has a reputation for some very fine steaks and salads. Â
 Affordable isn't usually a word you'd find when discussing the marvelous atmosphere and delicious menu that Middleton Tavern offers, yet the prices for drinks and food are very comparable to other establishments in downtown Annapolis.  If you're looking for a good deal check out their happy hour.  Not as great deal as their rival O'Brien's across the street, but still pretty darned good.
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