Chesapeake Landing Restaurant

The potato skins with crab were very good with great crab on the top. The main crab cake platter seemed to have had an entirely different crab meat with a bit too much filler. Waitress was missing for a while a few times and had to go to the counter to ask for the check, waited 8 minutes after we were finished with no show at all. It is okay. Price was pretty good but I would have been willing to pay more for better crab cakes. Good tater sauce and bad cocktail sauce.

We were told by a local that this is where they go for good seafood when in the St. Michaels area and she was right. We saw a number of the folks operating shops in St. Michaels eating in here. This is not a fancy place, but it serves really fresh seafood. You can tell because they have refrigerated trucks out back being loaded up with local seafood to be distributed elsewhere.
My wife had the stuffed oysters, which were excellent and I had a grilled crabcake, which was one of the best that I have had in a long time. Even the salads that came with the meal were large and very fresh.
When it came time for dessert, we asked if anything was made in house and our server said that only the bread pudding was made in the restaurant. We inquired about the Smith Island cake and she said that wasn’t made locally either, so we opted for the carrot cake, which our server recommended. It was excellent.
We also split a bottle of white wine, which was a recognized label and I was surprised by how inexpensive it was.
Overall, I would highly recommend this restaurant for food quality and value. Is there a whole lot of ambiance? Not really, but the food is awesome. If I were in the area, I would certainly go there again.

I have to admit that this is not the trendy, on the water, designer seafood place in town. This is the spot for the locals about 2 miles away from the tourist crowd.
Thankfully, that is what I was looking for.
The oyster stew, crab salad and seafood wraps are wonderful and inexpensive.
Bountiful portions and sides (potato salad and cole slaw are an art form; they do it well here). I hate I missed the evening oyster buffet, but plan to return. Steamed seafood, take out, and multiple desserts with a full bar make this a great dining experience. Be sure to try this spot when in the area.

The hierarchy around St. Michaels is (painfully) clear: the tourists, while appreciated, are lower than whale poop. Weekenders who own property are whale poop — and full time residents are the whales. So a restaurant that happily treats all guests as equals is a real find.
Chesapeake Landing is great. The staff is professional AND friendly; the food is local and really, really good. Anything with crab (crab cakes, crab-​stuffed shrimp, crab soup) is outstanding. Scallops are sweet, plump, and juicy. And the oysters — oh, my, the oysters! — are as fresh as you’ll ever get. Especially on…
…the Friday night Oyster Buffet. Raw on the half shell; steamed: lightly breaded and fried; stuffed (an Eastern Shore specialty); oyster fritters; oyster stuffing — all you can eat, along with a variety of other stuff. (Side note: fried chicken used to be on the buffet, but it wasn’t there this week. That’s a shame, because it’s incredible!). The price is reasonable. Make sure you make a reservation, because this is The Big Night and you may not get in without one.
The Landing also sells raw seafood including crabs and oysters in season. And it’s open year round; it’s a great place for a nice lunch on a cold Sunday afternoon in January. Enjoy!

I had a combination platter and was disappointed. The broiled seafood was flavorless and flat. I think the «baked potato» was microwaved as it was rubbery. The locals must not be particularly demanding.

Service was quick. My companion’s oyster stew was bland. My chicken and dumplings was overcooked and flavorless — my companion will eat almost anything you put in front of him so the fact that he wouldn’t eat the meal I couldn’t stomach is pretty telling. I’m told this is where the locals eat but our meal fell flat. I wouldn’t return.

After having a horrible lunch at a local place on the water, we were just hoping to find somewhere to get fresh delicious seafood. This place was awesome! We sat in the bar area and were greeted by our waitress right away. We had the crab stuffed mushrooms and they were all crab meat — no filler. We also ordered steak, crab cakes and snow crab legs. Our food came out timely, was cooked correctly and better than we had hoped. We will def come back here to eat.

Stopped there for lunch one day and had a burger. It was cooked to my liking on their grill. My wife had a turkey wrap which she enjoyed as well.
We stopped there before we left for home and bought some crab meat. They even asked if I wanted it packed in ice. Their take out seafood prices were fair for the area. When we got home that day we made some delicious crab cakes.

My wife and I split the crab dip, filet mignon with stuffed shrimp, and finished with the chocolate turtle cake.
If you like crab, you’ll really like the crab dip, it’s all crab meat and a few spices with a moment of silence for the ‘dip’. The filet was cooked perfectly. I enjoyed the stuffed shrimp, but my wife didn’t. She got a small piece of cartilage in hers; I’m not as picky about that.
The cake was excellent.
Given that we were just a few miles outside of St. Michaels, it was a good price for a well-​prepared meal. With two cocktails, the total came to $ 63 with taxes.

Next time I go, I will choose a simpler, «cleaner» dish that is just pure, fresh fish and seafood. I ordered the seafood stir fry and all the seafood (crab, shrimp and huge scallops) were great; the stir fry part really detracted from my enjoyment. One sister ordered fresh, seared tuna and it was perfect. Other sister ordered crab cakes and although it was really good, it was on the small side. Side orders of sweet potatoes, popular down here, were very good, as was the warm bread. Décor is all about nautical stuff on the wood-​paneled walls, the wait staff was friendly and thorough, and there is a bar area, as well as a retail area when you first walk in so that you can purchase refrigerated and frozen seafood items. There are rockers and a picnic table on the outside, front porch, and also «loud» and large posters on the fencing along the parking area. Ignore this part, and go enjoy some simple and fresh seafood.

Oh it made me sad — especially since it’s so close to home base. They were under-​staffed and it took forever to get our food which wasn’t the best (burger). I will go back and try again because it takes restaurants at least 3 months to get off their feet.

We got a recommendation to check out Chesapeake Landing from my boss who has a summer cottage near St. Michaels — «it’s where the locals go!» he told us.
We showed up around 7pm on a Saturday, and much to our surprise, we were easily sat immediately. Yippee! The restaurant definitely has sort of a 90s-​ish feel with the décor. It somewhat reminded me of like a Luby’s or something but it was clean and what not. We at least felt comfortable in shorts and tee shirts from being touristy and outdoors all day. Our waitress was really sweet and was there when we needed her but not around every 5 minutes.
We started with a few drinks — I had the apple strawberry sangria and my fiancé stuck to beer. The sangria was the only low point of the meal — it was just super sweet and not really my taste. I later switched to house wine. We ordered 30 medium crabs, macaroni and cheese, and fried green beans. The mac and cheese was delicious, definitely cafeteria style like the kind I grew up with, not the fancy gourmet kind we normally see in DC. I loved every bite, true comfort food. The green beans were delicious and crispy. Then came the real treat — the crabs. This was my first real time with eating crabs Maryland-​style. Our table was covered in paper, then they brought us a bucket and this giant tray of steamed crabs. I had no idea what to do, but another server saw me staring confused at the tray, and she expertly showed me how to shell it. 30 crabs later, my fiancé and I were happily stuffed.
The bill was surprisingly low — we each had 2 drinks, split the large order of crabs, and two sides — all for $ 60, with tip! That’s crazy for an excellent meal, a fun experience, and great service. I would highly recommend this place to anyone who is passing through the area.

Good was very average/​slightly below/​overpriced! Waitress was very slow, Tables were sticky and who puts bacon on a spinach salad? husband shrimp were overcooked, corn bread is a very dry/​oily corn cake. Sorry but I don’t think it’s worth it

Passing through the area at lunch time. Food was delicious, portions were good and service was friendly. Will stop by again when I return to the area.

We went there at the direction of a few locals who recommended it for seafood. We got as far as ordering appetizers because we were weary of the reviews. We got the bacon scallops and the crab pretzel. The scallops were overcooked and chewy. The pretzel was old, and chewy as well. The only good thing was the crabmeat which was unfortunately served with velveeta cheese. We had a glass of wine and a beer. The bill was $ 32 bucks. Would never got back again unless I was hangry and this was the only choice.

Look, don’t let the décor fool you. Yes it looks like a waterfront joint, but then again, look where you are, you are on a spit of land that is fundamentally surrounded by water, in a series of towns who are still heavily dependent on the work carried out by Watermen. The front is a seafood sales place and you can buy seafood there so all of the trendsters who are letting this be their driving criteria for a low score need to stick with Red Lobster.
We had dinner there last night (3÷14÷15). The food was excellent. It was cooked properly and delivered in a timely fashion. There were a sizable number of people there but we were able to be seated with no problem. The apps were excellent and we ordered bacon wrapped scallops and a cup of crab bisque. The scallops were perfect and the bacon wrapping done right, not scorched crispy but not greasy soft and they had stayed wrapped on the scallops, no toothpicks. The bisque was bland, but at least it wasn’t tainted with Old Bay. Also they serve you a basket that is a mix of break and cornbread, both of which were good.
My wife ordered the lobster tail (she just wanted a lobster tail) and I had the surf and turf. Steak was cooked as I requested and had a nice sear on it. the lobster was cooked correctly as well. The wait staff were friendly and made sure we were topped off with regards to our drinks.
And while there may very well be a eighties feel to the décor, it wasn’t dirty. It was clean and organized and looked very much like a real shoreline restaurant instead of a place that bought a bunch of sea-​themed chachkis like some chain restaurant. I would definitely recommend it to anyone in the region.
P. S. Today we went back and bought four lobster tails to take home with us. Fair prices there as well.

Don’t expect any special from the vintage 80s décor or the mediocre service. It’s all about the seafood. Fresh delicious and straight from the local waters. Can also take food to go from the seafood market. True favorite of locals.

By far the best seafood in Maryland, fresh, huge portions, well prepared and cheap! Wow did I love this place! I wish I lived close by. You know food is good when locals go there in crowds.

This place should be on Kitchen Nightmares. It looks like a bait and tackle shop up front, and looks like a timewarp to the 80’s in the back. My girlfriend asked what seafood was fresh and the waitress said «only the rockfish, oysters, and crab is fresh, everything else is frozen.» What makes that worse is there are over 30 different types of seafood at this poor excuse of a restaurant.
I ordered the crab cake sandwich (which by the way was canned crab, not fresh) and it was served with a side of tartar (which was mayonnaise only). My girlfriend ordered a ¼ lb of shrimp and had to return it because it was so overcooked it was inedible. The salad had frozen, old cucumbers on it and the onion rings were soggy and tasted like vinegar.
This place is truly awful in every aspect of a restaurant and its a shame because this island NEEDS some good food.

Epically bad. Honestly, we couldn’t truly tell if it was the service, the kitchen or both. But all we know is it was a terrible experience — worst I’ve had in a long, long time. We tend not to post bad reviews, only good reviews for places we really enjoy. But this was bad; so bad I just felt compelled.
I’ve lived in Maryland for many years, most of those years on the Eastern Shore, and I just don’t know how a place with the reputation that this place has could so badly mess up seafood. Imitation lobster in the $ 30 pasta dish. Cream of crab soup that was as pasty and gross as they come — straight out of the Sysco can. Stuffed flounder that, if it wasn’t for the mayonnaise that was the «crab imperial,» it may have been the driest flounder I’ve ever had. Stewed tomatoes that were just bland. At least the onion rings and corn bread was good — gave us enough sustenance to make the drive home.
And did I mention that we walked in at 4:30pm on Sunday afternoon and walked out at 6:45pm? There was only one other table (of 2!) when we sat down. Not kidding. Service was painfully slow and inept.
As common of a place there is. And if you’re from the lower shore, you know what I mean.