Chessie’s Wharf — Restaurant in Annapolis

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...

In West Annapolis, spent most of my day…. Waiting for a table! Arrived an hour after opening and the wait was 1-1.5 hrs. Went DTA and came back. Got a beer at the bar while we still waited. They had great guest taps! Highly recommend Triple crossing!

After we were seated we ordered our flights and food. We waited for about 20 mins for our flights to come however there was a problem as some kegs were empty without notice on the menu.

They had an extensive menu for drafts and cans. They also had a full service bar for cocktails. The beer was delicious and tasted fresh. They had an assortment of IPAs, stouts, and sours!

The food was a step above bar food. We had the chicken wings(old bay hot sauce), chicken sandwich and the pretzel bites with beer cheese. Our friends ordered some other food but their fries were disgusting looking. They did order a new batch for us and looked so much better.

Service was okay even-though it was busy. Our server didn’t seem happy to be there.

There isn’t much parking so we parked in the street. Both inside and outside are reservations only. The bar is first come first served.

The bathroom is single use only and only one of them has a changing table. Both of them are wheelchair friendly.

I would recommend coming here near opening or closing if you came in the weekends.

I am happy to see for RAR coming to Annapolis and helping out the West Annapolis Area. I recommend checking it out just be mindful of the potential long wait...

Located in West Annapolis where the Mexican Café use to be (which was basically demolished). Anyone who goes to Annapolis frequently knows that parking can be an issue. With only 18-20 parking spots, be prepared to park on the street (find a legal parking spot) and walk to the restaurant. I got there around 3 pm and it was not very crowded but when I left at 6 pm, the restaurant was packed.

Being a brewery, it looked like there were about 35-38 taps available with 15 RaR beers actually on tap and 8 guest beers. Also, plenty of canned beers available. There are 12-14 seats at the bar with other ‘shared tables’ inside. Outside there are 4 covered picnic tables (everyone was inside because of the weather). Bernie and McKenzie were our servers. Both very friendly and attentive. Beers ranged in-between $5 - $8. Additionally, you can get beer flights (four 5 oz pours) for $10 (RaR beers only). All the beers were excellent. Typical bar food – appetizers, a few salads and burgers/sandwiches. For an appetizer, I had the 1 lb Boneless Chicken Wings (Chicken Feast – JO & Malt Vinegar Powder) with blue cheese. A little on the salty side but very tasty.

As of today (01/23/24), no Happy Hour nor military discount. Merchandise was available. Don’t miss the ‘singing fish’ that are on the wall. On the hour “performances”. Overall, great experience. Look forward...