Jon Pruskowski
A great place for lunch and beers. Beer flights are a good way to sample the many beer options they have on tap.
The food is incredible. Shown in the pic is a triple smash brisket burger and WOW was it delicious! Wings were also very good. I tried the bbq+hot sauce blend on the wings at the recommendation of the server and was glad I did!
Highly recommend this place for a great meal and some beers in a pretty chill atmosphere.
… moreBrooks Perry
Chessie’s Wharf in Annapolis stays rolling out delicious burgers and ice cold RAR brewery beer ! Perfect for before or after a Navy football game or for watching sports with friends. Each burger comes with a Chessie burned into the bun. If you aren’t familiar with Chessie, it’s essentially the Chesapeake Bay’s take on Nessie from Loch Ness. The burgers were great – the perfect smash burger style – fries and tots were also delicious.
The space is on the small side but does have an outdoor area. It has a lot of long high top tables with 10-12 chairs and just a few booths. If it’s cold or poor weather, the small area does get packed and you may sit next to strangers.
If you’re a burger fan do not skip!
… moreDC A
I’ve been going to RAR Brewing in Cambridge since I discovered them in 2015/16. I was delighted to find them open a spot in Annapolis which is way closer to me on Kent Island than Cambridge. I’ve been visiting this location since 2025 & I like it a lot. I often order the fish & chips which are excellent. Well done Chris & staff and a bartender with a great name, Doug. Highly recommended!
… moreLori A
First, these are the BEST fruited sours I’ve EVER had. Absolutely delicious! The food is so fabulous, too. Our server is friendly and knowledgeable. We will most definitely be back! You won’t be disappointed!
… moreAshley Amian
Great selection of beers on tap, including lots of dessert beers! I’ve enjoyed the crushes here. Food is fine. Typical selection of fried bar food. Parking is very easy in this area.
… moreStefanie Yuhas
Everything on menu is great. Only thing we haven’t LOVED is the fish & chips but we overheard a waitress say recipe has changed since we last tried…so gonna have to give it a go next time. Parking is super tight which is a bummer but street parking is usually available. Indoor seating is all hightops except for 2 tables, so in less than great weather you may have quite a wait. Drinks and food are truly wonderful though, and the staff well trained.
… moreaaron thompson
Awesome attention giving from our bartender! It was busy but he still spent lots of time with us. Get the crabby pretzel!! Great beer and drinks to go along with the atmosphere. Strongly recommend!!
… moreJames Hawthorne
Had a great late afternoon lunch, the fish and chips was really enjoyable. Nice open area, with inside and out side seating. The customer service was excellent had an enjoyable experience.
… moreOlga Pachy
I had such a lovely experience at Chessie’s Wharf! I ordered the seasonal salad with chicken and a glass of wine — everything was absolutely delicious and so refreshing. The flavors were beautifully balanced, and the ingredients tasted incredibly fresh. The atmosphere is both lively and cozy, making it the perfect spot to unwind and enjoy a great meal. I’ll definitely be coming back
… moreRichard Collins
Great vibe. Knowledgeable and friendly staff. Great food. And the beer! Awesome! Best beer in Maryland and among the best I’ve had in the East Coast.
Loved it!
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