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    Chessie’s Wharf

    3.9 (88 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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    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.

    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.

    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!

    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.

    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!

    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.

    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!

    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!

    Coastal Shandy
    Natasha M.

    So I asked my Waze to take me to Annapolis and it took me straight to Melvin Ave. I was in the mood for a brewery and there was Chessie's, 400' away. I sat at the bar and the bartender immediately provided me with both the food & brews menus and I had to try the mysterious described Dark Side Deluxe and I paired it with an amply portioned fish sandwich. Both were decadently delicious. I also had the coastal shandy, which was just the right balance of sweet and hops. The tasting room was full of good spirits & vibes and the bartender always checked in on me to make sure I was good.

    Locals grabbing a beer
    Lisa G.

    We were kind of the last customers served for the day at 8:30pm - as an out of towner quite surprising the whole city's restaurants close at 9pm but overall great ambiance, tables were nice and big and mostly inviting Felt a little rushed to finish in 30 mins - beers were good just not great! We would love to come back next time through town

    Cheesie Deluxe no raw onions, fried instead
    Rob B.

    Wow, been dining in this building for 30 years but this rendition is 100% new! It's a beer bar at its heart but its open air atmosphere is a trip to the park! A beautiful place to come on a beautiful day. The menu is limited but the Chessie Deluxe burger, I substituted fried onions for raw, was delicious. The smash style burger was full of beefy flavor, unfortunately the roll is too soft to hold up to the delicious burgers. Outstanding service and friendly faces make the experience best in class!

    Triple chessie burger with bacon and a side of tots.
    Taylor L.

    I love love LOVE RAR. But I live in Kent Island and can't justify driving an hour to Cambridge for their draft brews. When I heard they were opening one up in Annapolis, I was so happy! I've been to Chessie's Wharf multiple times since it opened in late January and I gotta say it's always a great experience. A much quicker driver than heading to Cambridge! The staff are friendly and happy to be there, the food is always great and the beer is (as always) incredible. The interior role its namesake provides a nautical vibe that perfectly captures the location it's in. Every hour there's a wall of singing fish that will sing a song! The vibes are all around immaculate. Unfortunately I have to dock a star off although it pains me. Why? Well because as much I love this location it's incredibly small. The first time I went (over a month after it opened) it was packed. I had to wait 2hrs to be seated. It was worth it but I doubt most people will have the same amount of patience as me. Chessie's Wharf is an incredible small area with limited parking. The first time I went, I visited around 6pm on a Saturday night and it was packed the entire time with barely any room to stand. And unfortunately all the beer was tapped out that day (including guest drafts). All they had were cans for sale, which wasn't a problem especially since they offered me a chilled glass but it certainly was disheartening that the cans they had for sale were limited (RAR is a popular brewery i am unsurprised it doesn't help that they get their beer from HQ since there's no space to brew it from the location!) Every other time I go I always try to go when they open because by 1pm it remains packed pretty much the entire day. Even when I go before it opens there's usually a line of at least 10 people formed outside at least 20 mins before the doors open. Small space, parking and always packed. With it getting warmer I expect that to continue or get worse! Overall Chessie's Wharf is a great addition to the Anne Arundel County brewery scene. It's nice RAR is finally expanding beyond Dorchester county and its cans at various liquor stores in the state. I just wish that Chessie's Wharf had a bigger space and more parking. Hopefully RAR continues to expand to to the western shore and open another location in the next year or two.

    And cocktails

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    11 days ago

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

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    4 months ago

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    19 days ago

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

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    11 months ago

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    4 months ago

    Food was great, many beer options, and service was great. Open seating concept. Has a parking lot but fills quickly.

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    1 year ago

    The food and service were great. But don't plan on having a conversation. Very good atmosphere otherwise.

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    Crooked Crab Brewing Company - The cold brew and the pizza from elsewhere

    Crooked Crab Brewing Company

    4.4(214 reviews)
    12.5 mi
    $$

    I'm in Maryland, how can I not hit a brewery called CROOKED CRAB?!?…read more Pizza was on the menu... crisp thin crust and plenty of toppings. Beer was great, and I tried quite a few! Backfin was my favorite, I'll have to come back!

    I wanted to enjoy this place especially off the strength of two colleagues along with the reviews…read moreraving about this place. I will break it down with pros and cons. Pros: Great variety of beers on tap hefty pours on the tasting package Regulars come here to hang Plenty of seating Extremely chill...we brought a game and were able to play while we enjoyed our drinks Cons: If you have dietary restrictions you will starve; I have a gluten allergy and could only order the wings as the menu is limited to one brisket sandwich, wings, or pizza. They also did not have gluten free or cauliflower crust Many of there beers on tap are not updated on the menu so unless you inquire with the staff you will not know as I ordered a mead that was not included on the menu This is a self serve place, you go up to order and they bring it out to you I will not go out of my way to visit again as we left hungry and then had to make another stop; however if in the area would return again. if ocmpared to Jailbreak Brewery I would choose jailbreak everytime.

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    Crooked Crab Brewing Company - Inside right

    Inside right

    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

    Crooked Crab Brewing Company - Crab Cannon is good! I'm at the bottom.

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    Castlebay Irish Pub - a whole bunch of bottles

    Castlebay Irish Pub

    3.4(110 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.

    Great local Irish pub that made us feel welcomed. Nikki was our bartender and treated us like we…read morewere friends. The burger was delicious! Caramelized onions made just right by Kenny the cook! Thank you for the exceptional experience!! See you next time

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    Castlebay Irish Pub - Great ambiance

    Great ambiance

    Castlebay Irish Pub - Bourbon - note the top left, a whole collection of Pappys

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    Severna Park Taphouse - Check out all our week day specials, including hand tossed pizza and calzones every Thursday

    Severna Park Taphouse

    3.6(241 reviews)
    8.2 mi
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    This is a go to, laid back spot where you can get some quick, easy bites.. The drinks are well…read moremade, and the food is good as well. I usually get the crab dip and black and blue burger. I've also had the beyond burger as well, which was good. Service is usually pretty quick, even if it's bus. The atmosphere is very chill as well.

    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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    Severna Park Taphouse - Lobby

    Lobby

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    Fried haddock sandwich with fries

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    Frisco Tap House - Seasonal veggies

    Frisco Tap House

    3.7(421 reviews)
    10.0 mi
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    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

    Representing 2024, F is for Frisco Tap House. Been here a few times for Tuesday night trivia &…read moreonce a Saturday during the day for trivia semi-finals mostly in 2023. In May 2024, I brought my girlfriend to trivia. In July 2023, I had brought a prior g/f. I've gotten food here a few times, occasionally just a drink, sometimes I just drink water depending on what's going on. I've never been impressed with the food. I got a steak, quesadilla, etc., and nothing is great. One time I was considering getting a burger, and I found out that they had pork in their burgers, which is wrong; I don't eat pork. The only thing that was great was their pretzel, which I had a couple of bites of someone else's on that Saturday trivia semifinals, in which I had plans for my birthday late lunch birthday deal over in Annapolis. I needed to get there by lunch time as the price is a lot more expensive at dinner, which starts at 3 there. Drinks are good here at Frisco. Service can be pretty slow here sometimes although last time I was there 2 weeks ago, they were surprisingly fast. The 3-stars is mostly for the mediocre food.

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    Frisco Tap House
    Frisco Tap House - Shrimp avocado seasonal

    Shrimp avocado seasonal

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    Chessie’s Wharf - bars - Updated May 2026

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