Chessie's Wharf — Restaurant in Annapolis

This is a very trendy, over-stylized restaurant offshoot of the RaR brewery with a tiny parking lot and ok but not great food. The first time my family tried going the lot was packed so we went somewhere else. we eventually went out just the wife and I for date night months later. I'm not a fan of the communal tables. It was very cold outside so our only options were the bar or joining a bunch of large groups with little children at the communal tables. They only had 2 tables of 4 seats in the whole place and both were taken. We sat at the bar. The bar stools look cool, but no back and no cushion and although it is bolted to the floor mine was kind of wobbly. looks cool but not great in execution is kind of the theme of this review.

We got the wings and the tots to start. wings were ok, but small. Tots were the best thing we ordered. Did 2 flights of beer and shared them with my wife. Some were ok, none we were wild about. The menu said they could only do flights of the core beers but the bartender said he could do flights of any beer on the menu that were RaR brews. We both got burgers. they aren't listed on the menu as smash burgers, but that's what they are. they were ok. The bun had chessie burned into it but besides that there was nothing special about them. standard smash burgers. style over substance. I was happy that my onions were genuinely caramelized instead of just seared on the flat top for a few mins. sides like fries are extra.

Overall kind of trendy and hip but "meh" experience generally indicative of the Annapolis restaurant scene. they had a very large portion of the building dedicated to their merch. merch is all well and good, but you don't need a whole deli counter dedicated to it unless you are a tourist trap. plenty of better places nearby that just aren't trendy. if you want good beer, go to the old stein inn. for really good burgers, chad's.

Also the restaurant has only 2 unisex bathrooms. not nearly enough for a bar this size. we went on a Sunday night before a Monday holiday and there was a line to the bathroom. also they need door handles that indicate if the bathroom is...

We are a family of five that eats out regularly. We dine all over and have no issue spending money on a quality experience. First, the good, our server greeted us promptly, was very friendly, took time to explain the menu and gave a couple recommendations. His service was excellent throughout and as such the 5 star rating for service. Second, the place is just great from an atmosphere standpoint. West Annapolis is a gem and this place fits right in. We sat outside and I could definitely see a nice fall afternoon sampling beers with Navy football in the background. Lastly the food, this is where things fell off considerably in terms of value. This place seems to be suffering from shrinkflation in the worst way. A family that order one pretzel bite app ($11, but then added beer cheese for another $3.5 was effectively what looked be 2 pretzel sticks cut up). The single burger reads on the menu at a reasonably priced $11, until you want cheese $1, bacon $2 and some fries $3.50. Now I’m not opposed to $16.50 for a burger and fries. What I am opposed to is effectively a glorified slider. One of our kids literally ate it in about 4 bites. Similarly, my wife ordered a house salad ($14) and added chicken $7. It was one chicken tender cut up on the salad. Again, no issue with a $21 salad if it has more than 4-5 bite sized pieces of crispy chicken. Finally, my cheese chop which is their version of a cheesesteak. Was recommended by our waiter and the flavor was very good. It was however $17.50 once the tots were included. It was effectively a hot dog roll with about 2.5-3 oz of beef on it. My wife and I were astonished. So I guess we will stick to stopping there for beers and perhaps and app but we couldn’t in good faith recommend for dinner with a family that includes multiple children/teenagers based on what they are putting out. As always, YMMV. Our total for a family of 5 with tip with about $185 that included one round of drinks...

This is our favorite watering hole. The staff is really friendly, they have a great team, service is ace even when they're slammed. Orders are taken and filled really quick.

Love the outdoor space and the fisherman's wharf design of the building. All the details at this joint are thoughtful, playful, and intentional. It makes for a fantastic place to hang out with friends or kick it by yourself to kill time.

Some comments say the table design is cramped. I find it cozy. But folks who can’t squeeze through tiny passages for whatever reason might find the picnic tables on the patio the only comfortable seating (they have heaters and fans out there), and the indoor space might not be easily navigable.

Anyway, beyond potential accessibility issues, the craft beer selection is unmatched. RaR makes some tried and trusted beers, some of the best in the area available on draft, and on top of that the brew co. keeps an extensive rotating selection of new beer/ale creations brewed by them, plus a rotating draft/can menu that always has good picks. They are known for their IPAs and incredibly unique, diverse fruity milkshake sours. Also fun seasonal cocktails, and a wine list.

I love the straightforward but actually good food menu. Yes it's burgers sandwiches tots fries like any brewery, but it's not greasy or huge portions. You can get a good bite to eat and beer.

Go here. Actually don't, because given how great it is, it gets crowded. But the wait is never long and you can pack in around the bar or building while waiting...