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Chessie’s Wharf

3.8 (97 reviews)
ModerateBars, Brewpubs, Burgers
Closed 11:00 am - 9:00 pm

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CHESSIE’S WHARF ATMOSPHERE

What's the vibe?
Loud
Good for kids
Dogs allowed
Outdoor seating

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Recommended Reviews - Chessie’s Wharf

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Unreal Smash burger
Mark J.

The BEST smash burgers in Annapolis. I'm talking 10/10. Crispy lace beef to perfection. Great drink selection as well! I can't wait to go back.

Crab Cake Sandwich
Nneka W.

Love this place! I'm not a beer drinker at all...BUT this is a fun place to open up your pallet to the idea of bear. Their beer is different than any other beer I've had, and that's not a bad thing. They brew their own beer which makes this place more special.Their beers are lactose so they have a more creamier vibe, especially the sours. They also sell their beers in cans, which I've taken advantage of. I normally get a flight just to taste different beers to see what kind of beer I actually like. They also have regular cocktails which are pretty good (about $13-$15 each). The service has been consistent the 3-4 times I've been. Their servers and bartenders have always been friendly and helpful. The set up makes you feel like you're near a beach with all the windows and patio seating, etc. The music has also been pretty decent. The food is probably the best bar food I've had...seriously. The food is pricey...especially when their 5 $17 crab balls. The crab balls didn't really have filler at all and they were tasty, but too expensive for the quantity. Their burgers/sandwiches are smaller than a regular burger but honestly the perfect size from a business perspective, that's the case with all their serving sizes honestly. Anyways, their burger is juicy well seasoned and the crab cake sandwich is decent. The crab cake sandwich isn't the BEST crab cake sandwich I've had, but it wasn't bad. I would get the burger over the crab cake sandwich. Their Honey Old Bay wings are my favorite so far out of their wing flavors. Their wings are the perfect size and fried just right. The parking lot can be tight but there is also plenty of parking on the street. Check out the cute little ice cream spot down the street too!

Outdoor signage at night
Wesley H.

A litany of beer options on tap and to go if you like. Well lit atmosphere with great service. The food was top tier. The brisket burger was my favorite. The loaded tots with crab meat on top was a nice change of pace. I plan to try them with their chili next time. I did have a chili cheese dogs. Standard hotdog was the chili was very good might I add. I like that this spot had a guest list for on tap brews. I I'll definitely be returning very soon. I think our bartender was Kenny? He was great. My apologies if I messed up the name.

Burger with tater tots
Rebecca H.

I thought the food here was decent. The burger was good and came with tater tots. The fish and chips were good too but I think other places in Annapolis have better fish and chips. I liked the cocktail that I had. It had bourbon, mango puree, agave, bitters and lemon. Overall the food was good, but I'm not sure if it was memorable enough to come back again. The service was great and the place had a casual and open layout.

Kevin S.

We stopped by for snacks and drinks. The outdoor patio was perfect for the beautiful Saturday afternoon. This Wharf is walking distance from the Navy Marine Corp Stadium. The RAR Oktoberfest hit the spot. We smacked on the pretzel bites and tater tots. Friendly staff that offered drink suggestions. Nice pre game before heading downtown.

beer flight
Jessica S.

Picked this place for the chill atmosphere, outdoor seating, and wide beer selection. When we arrived there was some confusion about how to get seated as there's stairs and people waiting around for tables and no real "host service". We went to the counter and surprisingly, even though there were empty tables and bar seats, we were told there's a 25min wait because "there are people ahead of you." I assure you it was not 25 min and there were not many people seated before us. in fact, more people left so this was confusing. Got drinks at the bar but children aren't allowed there and they don't have any waiting area. Just FYI. Otherwise it's a kid- and dog-friendly spot with kid menus. Also asked about the happy hour menus that were displayed on a holiday Monday. Was assured there was happy hour by the host boy, but when we ordered we were told there's host boy was wrong and they took the menus away. Ok. It's not like this was the beginning of the shift at 11am--no it's 2pm and you have to wonder if people who ordered before were able to enjoy a deal that was withheld from us specifically. The food portions were small for kids and even for the burger. Ended up ordering an extra fries just to fill us up better. The affogato martini was special and cute but a little too sweet. I think vanilla ice cream with liquor was just a little too much. Should've been adjusted with something bitter rather than the same formula as an espresso martini. The beers were evidently good and other than the confusion and poor service from a select individual we had a good experience and would return.

Flight
Jess L.

Second time coming here and a great experience both times. It is a small restaurant with a small parking lot - we didn't have to wait for seats or parking this time but be prepared you may have to. There is street parking in case. My husband and I sat right at the bar on a Friday night around 7. It was crowded but there were a few seats. We each got a flight, split tots, and got burgers. There are a TON of beers on tap - definitely recommend a flight! If you've never been, RAR has really crazy sours! We each tried a few and they were all insane and delicious! They had a Cinnamon Toast Crunch cereal inspired sour - amazing. Foodwise, it's a small menu but everything we got was great. The burgers are $11 for a single for $13 for a double, no side included. We split an order of cheesy tots. Everything was great - the burgers are kind of smash burger style. Our Bartender was attentive, and our food and drinks came out fast. On our way out we got a bunch of single cans to take home - I love that you don't have to get 4 of a kind! They have a TON of flavors so make sure to check that out. Overall, we had a great time, food and drinks are great. In the summer- they have a nice patio! Only suggestion is to get a few more low top tables as folks with mobility issues need these and there are only 2 inside. We'll be back!

Seasonal mixed drink
Teresa R.

First, let me say that we were very surprised at the ratings for this place. We stopped here on our way to the Navy football stadium. When we arrived, we were greeted by a very nice young man who seated us within a few minutes although it was pretty crowded. Our waiter was Douggie and he was not only funny but had great recommendations and answered our questions with detail. He made our experience amazing. I ordered the "You Wild," wings which were a combination of BBQ and Buffalo sauce! I absolutely LOVED them! I asked for a side of sauce and it came out quickly. I also loved the painkiller drink! It was very tropical! My husband had the brisket burger and tater tots. He said both of them were absolutely amazing. It was a very lively restaurant with lots of nice Christmas decorations. We sat family style with other groups and were lucky enough to sit next to 3 people that we talked to the entire time we were there, making the experience all the better. We will definitely be visiting here again when we go to Annapolis! We highly recommend!

Rachel S.

Come here a lot! Love the rotating beers but my fave is country ride and the Hefeweizen! Love their happy hour- I got a $2 hot dog and we also got nachos! $5 RAR beers for HH as well. Love sitting by the bar but the outside is nice too especially in the warmer months. Love the bar tenders/ servers they are great and quick to refill your beer! Definitely recommend!

Coastal Shandy

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23 days ago

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2 days ago

Great customer service. Good food and beer. Bots was very friendly and made the experience very enjoyable.

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23 days ago

Came in here yesterday and the host with a bad fake tan was literally too busy drinking an alani and burping to help me

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3 months ago

Cool spot good beer good food good service I would go again when traveling though Maryland again.

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3 months ago

Wonderful burgers and service! We will definitely be back. Ambiance is fun. Great spot off Beaton path.

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Crooked Crab Brewing Company

Crooked Crab Brewing Company

4.4
(222 reviews)
12.5 mi
$$

We've been big fans of Crooked Crab for years, always taking family and friends from out of town to…read morevisit for the beer, the pizza, and vibes (which is really saying something coming from a native New Yorker!). So, it was a no-brainer to choose them as the venue for our wedding's welcome party. The pricing was very reasonable for such a large space and served as the bar tab for all our guests. We opted for in-house catering, and the pizza and wings were delicious as always. The staff was super accommodating and wonderful, making the food service, bar, and audio/visual a smooth experience. Our guests had an absolute blast and it was a great way to introduce so many of the people in our lives to one of our favorite Maryland institutions. Thank you Crooked Crab!

After traveling five hours I was hungry, thirsty and will admit maybe getting one claw crabby…read more Everyone here was awesome. Welcoming and friendly even when I tried to order at the bar instead going to the place at the end to order as the sign clearly states. Sorry I was born in Wisconsin. The wood fired Meat Lovers Pizza was tasty and enough for two. We had a pretzel order and the mustard was spot on. Our beer choice was Stringray Mysterio a very good stout. Also myself the navigator needed and wanted a Mead. So Pina Colada Crush was a perfect choice. We both loved the decor and vibes. The pizza oven which was a crab design was cute but I thanked the men preparing the outstanding pizza. All the staff were fantastic.

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Crooked Crab Brewing Company
Pep n' step pizza - Smoked mozzarella, house made red sauce, beef pepperoni, cupping pepperoni, jalapenos, red pepper flakes, hot honey
Pep n' step pizza - Smoked mozzarella, house made red sauce, beef pepperoni, cupping pepperoni, jalapenos, red pepper flakes, hot honey
Crab Cannon is good! I'm at the bottom.

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Crab Cannon is good! I'm at the bottom.
Castlebay Irish Pub

Castlebay Irish Pub

3.3
(113 reviews)
1.2 mi
$$

Annapolis houses the Naval Academy, but a visit to Annapolis would not be complete without a stop…read moreto Castlebay Irish Pub. Visited with a bunch of guys after touring the Naval Academy campus...a short walk from the campus, it's a great Irish pub with a great ambiance and selection of Irish beer on tap (Guinness, Harp, Smithwick, Kilkenny) as well as the usual American brand. In addition, it houses a great selection of whiskeys: Irish (Bushmills, Jamesons, Red Breast, etc. - the different varieties), bourbons (to include Pappy's, Blanton), scotch (MacAllans), etc. The dining experience pairs well with the beer and whiskeys. The meat for the reuben sandwich and traditional corned beef are selected and prepared in a traditional manner making it delicious. If you are lucky, you will meet the owner of the establishment, who will regale you with stories about past Academy graduates who would return to the pub after graduation or even about his playing in a rock & roll band. Great food, beer, whiskey, atmosphere, and if lucky, great stories and an experience. When visiting the Naval Academy, take a yonder down the street, you won't regret the visit.

TERRIBLE experience, and not just for us. Bar was nearly empty when we arrived (fewer than 10…read morepatrons), had the World Cup game on mute despite advertising it on the door, and refused to turn up the volume when asked. A patron next to us asked just before we did and got refused too -- then was abruptly cut off and denied service shortly after talking to us about their own bad experience there. ANOTHER patron, came in after we did, was also treated rudely and refused service. My own issue: ordered a lemon drop with tequila (not vodka.. it makes me sick). First one was fine. After a bartender shift change, the new bartender -- who was actually the shift lead -- made my second one, and it was clearly off; I suspected vodka was used. I asked for it to be fixed, was refused.. So I sent it back, and asked for it off the bill. Paid my tab in full, then noticed at tip time the charge was still there. Server said the bartender wouldn't remove it. When I spoke to him directly, he blamed me for ordering something "nobody knows what it is," and when I said I'd dispute it with my card instead, he attempted to snatch my card off the table. I refused to engage further with him, asked for someone else (refused AGAIN) so I left.. I will be disputing the charge with Amex since he was the only one with register access. Multiple tables treated poorly in one night. SKIP THIS PLACE!! Smug and disrespectful bartender pictured..

Photos
Great ambiance
Great ambiance
Bourbon - note the top left, a whole collection of Pappys
Bourbon - note the top left, a whole collection of Pappys
Castlebay's Irish Pub

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Severna Park Taphouse

Severna Park Taphouse

3.6
(241 reviews)
8.2 mi
$$

Stopped in for a few drinks and a bite to eat. Amazing food and service was even better. Adam…read morecontinued to go above and beyond during our entire visit. He was very personable while also being attentive to our needs as well as his other tables. If you ever go to Taphouse, ask for Adam!

I came to Severna Park Taphouse with a large group of 13 for lunch on a Sunday. They were able to…read moreseat us in their ample outdoor seating. The service was great, friendly and fairly fast for such a large group. Unfortunately that was the only good aspect of this. The drinks were served in plastic disposable cups. Very wasteful. If I had known I would've just brought my own reusable water bottle. When the food came, several burgers were cooked incorrectly. I got a veggie and cheese quesadilla and the buffalo cauliflower appetizer. The quesadilla was alright but way too oily. It was basically sopping in oil. The sides of pico and sour cream came in tiny plastic containers and seemed store bought; the sour cream was separated with overly thick cream surrounded by liquid. The cauliflower was supposed to be "flash fried" (whatever that means) but it was honestly terrible. Soggy and mushy and soaked in a super strong buffalo sauce. The other people in the group who ordered burgers commented that their food was dry. This place honestly should be treated as a bar where you'll come to drink their extensive offering of alcohol. The food was pretty terrible and I will not be coming back for it.

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Lobby
Lobby
Fried haddock sandwich with fries
Fried haddock sandwich with fries
Outdoor seating

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Outdoor seating
Frisco Tap House

Frisco Tap House

3.7
(422 reviews)
10.0 mi
$$

Cousin Frisco Tap House…read more I absolutely love this place! The customer service is top-tier every single time we come in, the staff goes above and beyond. We usually pull up deep with our car family, and they handle our large group with so much patience and positive energy. It never feels like a hassle to them, which says a lot. Frisco has really opened its doors to our car community by hosting a Cars & Coffee series, and that kind of support doesn't go unnoticed. You can tell the whole team genuinely welcomes us they treat us like family every time. Now let's talk about the drinks...always on point! I'm a lightweight, so I only need one, and somehow they manage to make it just right because about two hours later, I'm exactly where I need to be...knocked out in my bed . And listen...THE CHICKEN & WAFFLES?! Hands down my favorite. So damn good every single time. Crispy, flavorful, and just hits the spot. If you haven't tried it yet, you're missing out My goal is to try lunch/dinner menu!! #tellemdivazincsentyou

This was my first time coming to Frisco. It was the afternoon so not busy but the main bar was…read morepretty packed but it is Friday! Christian was our server and he made good recommendations for items to try. As I mentioned it was a Friday afternoon so it was busy in the dining room area in the back so I can't wait to come at night to see its true atmosphere.

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Frisco Tap House
Shrimp avocado seasonal
Shrimp avocado seasonal
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Chessie’s Wharf - bars - Updated July 2026

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