Chessie's Wharf

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.

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! 🍔🍟

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!

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.

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.