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    Chessie’s Wharf

    3.9 (91 reviews)
    ModerateBars, Brewpubs, Burgers
    Closed 11:00 am - 11:00 pm

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    CHESSIE’S WHARF ATMOSPHERE

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

    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!

    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!

    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!

    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

    Triple chessie burger with bacon and a side of tots.

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    2 months ago

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

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    1 month ago

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

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    5 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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