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!

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!

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.

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!!

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.

We came here with family who live in the area, and we loved our visit! Great service and food, and really good beer and mixed drinks. We ate on the patio and had a 5 month old baby with us, and had room to take the baby on walks, and enjoy a very leisurely dinner with very tasty drinks and food. Fish and chips, burgers, and crab and cracker ball appetizers were perfect. The beer list was good with lots of other local beers included, so we could get a nice sampling of Annapolis area breweries. We'll happily return here when in the area next time.

Food and service were fabulous . My wife asked me to come again during the fall season. Strongly recommend visiting if you're in the neighborhood.

8/3/2024 2.5 Star Ambiance: cozy industrial brewpub. Thank God it's NOT another kitschy sports bar. Loud music playing but still family friendly. The family-friendly environment may subject to change once night falls for a "rowdier" crowd. Clean, not cluttered. There are both inside and outside seatings. Parking lot is very small (maybe up to 10-12 cars), but it appears to be street parking. However, it may be difficult to find parking space anywhere or one may find themselves parking far away and a long walk from the establishment if they happen to arrive after 5pm on weekends. Seating between bar seat is spacious, (not cramped up like most bar seatings). However, not a lot of tables inside the establishment. Seating issue and crowding arise once it becomes a full house (especially, on weekends). Service: we were greeted immediately and shown to available seating at the end of the bar. Staff are hospitable, not pushy. Foods came out at a decent time. Foods: plenty and variety of ales are available. Cocktails, wines and spirits are also offered. Menu is small, which is a good thing because one is relying more on the sales of alcohol rather than foods. Hopefully, the foods are freshly made with a smaller menu. Sandwiches and burgers are pricey without any sides to their orders. We ordered an ale, Southside Mojito, the crab cake sandwich ($26), a lobster roll ($32) and a side order of onion rings ($4). We had better beer battered onion rings as these lack seasoning. The drinks are good. Crab cake sandwich: where's the crabs? Where's the old bay or seasoning? Heavy-handed on the fillers and salt. Small portion for a sandwich (rather it's between a slider and a sandwich portion). It DOES NOT come with any sides. Lobster roll: again, where's the seasoning? Where's the lobster? Again, Heavy-handed on the salt. Indeed the roll is buttery and lightly toasted. But for $32 (listed as market price), the roll was about 5-6 inch (like a mini hot dog roll). And it DOES NOT come with any sides. The bigger picture - people may come for the beers, ales as it's a cute neighborhood brewery/pub. And it's new. But for the long term investment and power stay, the prices should at least match the sizes of sandwiches/burgers/sides. People will spend the money for alcohol, and for that in itself, the sandwiches/burgers should come with sides. As a brewery place, you depend more on the alcohol rather than the foods. Having bar foods is an added bonus. The tater tots, fries, onion rings are not that expensive to buy (as you buy them in bulks) - compared to how much they are being charged at this pub. The bottom line is - will we return? Maybe twice a year, not as often. And only for the alcohol. We don't mind paying the hefty prices, if the foods are great. But in this instance, the foods are edible and the portions are small - definitely not worth the many trips when there are better establishments nearby.

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

Delicious food, fun ambiance, great service! Next time I really want to try some wings, they looked so good! Also, if you're a fan of funnel cake, you'll Love the fried Twinkies!

It's loud, the bar seats are incredibly uncomfortable...but sipping on a Nanticoke Nectar and scarfing one of their deluxe smashburger (with jalapenos) is still worth it--even if I have to stand up and wear noise-cancelling headphones! It's not a steal as the prices are a little higher than you might expect (but if you're broke they do have a $3 hot dog!), and it's definitely not a large burger...but one bite and all the minor deficiencies are forgotten in a miasma of gustatory delight. Nectar lovers can also opt for a special treat of Jalapeño Nectar. Friendly (and busy) bartenders know their stuff as well. Def worth a visit, imho.

We came with our dog on a hot summer day and our server brought him a bowl of water (with ice) without us asking. We really appreciated that! Sitting by the tables on the right of the restaurant provided some nice shade and breeze. We enjoyed our wings and lobster roll. The orange crush could use an extra splash of liquor but it was refreshing.

There's a lot love about this place. First, let's talk about the BEER, food feedback at the end; There are a lot of breweries. They're not all good... then there is RAR. They made a name for themselves in the very out of the way town of Cambridge, MD and people would STILL travel hours and line up for another hour to buy the beer. It's that good. The beer is excellent. All of it. Some of the best around. Some reviews here have talked about cost, so let me put that into perspective; They have $5 pints every day! ...along with $6 and $7 options. You can sit in Annapolis and drink their very flavorful Lite offering for 5 bucks. That's not bad. The beers many come here for would be the New Englands and Fruited Sours and those are $9 pours. While it is more than I like to spend on a beer, from the source, at least it is a 16 oz pour!! You do not have to search far to find breweries giving you sad little 10-12 oz. pours for the same price. So have a couple of the high ABV pints, enjoy them, and jump to the $5/$6 options which is what you should be drinking anyway after those 9% hazys. They have flights for $10! Four different Four oz. RAR pours for 10 bucks. That is pretty good. You can sample beers that people are lining up next to you to buy in $9 to-go cans, but you get to try several different varieties fresh from the draft. And finally, in addition to a huge selection and variety of their own beer, they have a constantly rotating selection of guest taps. Usually 2 beers each from 4 different brewers. It's a different list every time I go in. They also have a full liquor menu of craft cocktails I'd like to try. I have seen many of them served, made with extreme care, and guests seem happy. With all that, it is not a surprise that this place has been packed every weekend and most weeknight evenings. It's a mixed blessing, of course. You want them to do well, but you would like to get a seat. They do have a large outdoor heated deck that is just going to keep getting better as the weather warms up. The staff is great- Management, bartenders, and servers. Very friendly and enthusiastic. If they had any opening month bumps they are constantly correcting and hiring new staff to fill in. I'm sure the popularity, while appreciated, exceeded their expectations and they would have doubled the size of this place had they known. That said, it's really beautiful inside with long community tables that make you feel like you are in a proper social beer garden. Get to know your neighbors. Enjoy it. The FOOD is all excellent but served in comically small portions. There is no getting around that. You look at the menu, you read the descriptions, your sandwich comes and you did not know they even made rolls that small. It is unfortunate, but just know that ahead of time. You are getting child sized meals but at adult quality. Look at this as a place to drink great beer with friends. The food should be something to munch on while enjoying a draft. If you come with a group as a dinner spot you may be disappointed. If cost is not an option for you, then just order extra food/sides and you'll be fine. I look at this as a place to drink that has snacks, rather than a place for food that has beer. I tried the Chessie Burger which is an excellent smash burgher. Nothing not to like but the size. Same with the Cheesesteak. I was shocked by the tiny bun, but it was stuffed full of rib eye with a unique beer cheese sauce. The loaded tots vary... sometimes they can use a little more "loading", but all good. The Fish and Chips are a unique offering to this location and were very good, if not small. The couple next to me got the lobster rolls which are listed as market price and cost $35 each. They were plump chock full of lobster, but they were turned off by the amount of food they got for the price. Buffalo wings look great. They are sold by weight so you'll get a pound of wings which seems on par, from a portion standpoint, with other pubs. My friend got the veggie burger and said it was probably the best veggie burger he's ever had. Only other nit is the servers will ask you if you want chips or side of sauce (when I asked for hot sauce for my cheesesteak) but all that is an added cost. It's not a lot, but just ask "how much" anytime someone offers to bring you something. It's okay, I know that's effort on their part I just wanted to know up front. So, by the time I added a small side of potato chips and hot sauce, my mini cheese steak was $16. I've had $16 cheese steaks that were the size of my arm. This isn't that. So, even with a couple nits up top, yes, this place is still 5 stars. How could it not be? They have no reason to increase the portion size of the food when you can't get a seat on the weekend as it is. :) Come for the beer! Everything else is just gravy on your experience. Such a well planned out establishment. Enjoy. Bring friends. Buy some 4 packs to-go.

My boyfriend is a RAR Brewing fan so we decided to check this spot out. While the place and decor are nice and fit right in with Annapolis, it is very loud inside and hard to talk to each other. Service was okay. Waited maybe 10 mins before anyone addressed us, then maybe another 5 mins before our server arrived. We ordered drinks and loaded tots with crab meat. The tots were good. We eventually ordered a burger and their lobster roll. While we were sitting there sitting our tots and enjoying our drinks, I was watching all the food come out and the lobster roll came by. It looks awesome so I thought I'd give it a try... a little disappointed as the roll wasn't toasted and it was half claw meat and half what I guess was lobster meat kind of shredded/spirals, almost like it was langostino or something. It was actually a little weird. My boyfriend said the burger was good. Not sure we will be back because tots, two drinks each, lobster roll, burger with onion rings was $110 not including tip.

Wait time about 20-25 minutes. I got the text via toast app to let me know my table was ready. Def Order a beer while you wait Or walk around and enjoy the breeze. Good music, good vibes. Great ambiance of chill and laughter. Congested but still spacious. Family friendly. You have the option to sit indoor or outdoor. A busy Thursday night but we got our meals out in time. Staff were attentive despite looking like chickens with no heads. Food was great, single patties cooked well done. My fish and chips cooked to crisp, well done. Our drafts were a combination of funk... fruity, and spice. Hubby and I also shared the foam lovers rock a draft of a coffee lover's delight. Bathrooms clean and tidy and there's a baby station available. Def enjoyed my time here with my family and our meals hit the spot. Get yo' brewing on

I'm a big fan of the affiliated RAR Brewing brewery/foodpub out in Cambridge so I put Chessie's Wharf near the top of my list of spots to check out when I heard they were expanding closer to the DC area. Chessie's Wharf just opened last month; drove up from Fairfax County in Virginia late Sunday afternoon last week to check it out. First thing I noticed was that it seemed to be in a prime location in West Annapolis within just a 5-7 minute walking distance from the Navy football stadium, which was nice. There was limited space in the parking lot, but I was able to find a spot and there is plenty of (free) street parking available on a Sunday. Upon entry, the place was smaller than I thought it would be, though was very packed for both inside and outside seating. There was a bit of a waitlist for seating but, luckily, a spot opened up at the bar after 5 minutes or so so I grabbed that. RAR Brewing is known locally for their excellent craft beers, though they're probably most well-known for their Out of Order series of sour ale (fruity sour) beers. These beers were available in abundance at Chessie's Wharf (and happen to be my favorite series of beers from RAR), so I ordered a couple pints, including the Blueberry Birthday Surprise smoothie, as well as a flight of their other flavors. The beers were all fantastic as expected. I did notice that the pricing for most of their 16oz pints was $9, which is slightly higher than their pint pricing in Cambridge. Flights of 5 of pretty much any beer you want at a smaller size are also available, though I don't recall the pricing (though remember it was reasonable). In addition to beers, RAR Brewing also has very solid pub food, in particular the popular Chessie burger, which I've for a long time felt are some of the best burgers in the D.C. area. I ordered the burger here at Chessie's and the burger was great, just like it is at the Cambridge location. Like the beer, I noticed the burger was also slightly (by maybe a $1 or so) more expensive than it is in Cambridge (was $11 just for the burger a la carte). Overall the food and drink menu they have at Chessie's Wharf is basically the same as what they have in Cambridge so if you're familiar with the selections there, they apply here as well, albeit slightly pricier it seems. (The food/drink at Chessie's Wharf and other RAR Brewing locations is a bit pricer than most other food pubs you may be used to) Chessie's Wharf has most of the other RAR beer offerings available, such as the Nanticoke Nectar and Pulp, and even has beer offerings from other popular outside breweries like 450 North and Dewey Beer Company. With that said, and as a warning, quite a few of the beers stated on their menu actually weren't available; the bartender ended up having to write down for me the list of beers available for the type I was looking for. The fact that there was only one TV for the seating inside with no TVs directly facing the bar was also slightly off-putting. Despite (minor) concerns about lack of seating space during peak hours, number of TVs, and pricing - the high-quality local craft beer and high-quality food means this spot definitely gets a recommendation from me. I'll definitely be back when I find the time!

Expensive mediocre crab cake, service kinda slow. If you're not drinking beer this isn't a spot you should go to.

The atmosphere and location is great. The food is average. We had the loaded tots, fried fish, and two hamburgers. The fish was really bland and the texture of the breading was pancake like. If I went back, I would just order the burger and fries and I would possibly try the wings. It's not the best burger as it is lacking flavor. You can get on the waitlist from their website which is convenient.

Such a cute place! My husband and I went for a lunch date and we had a great time. It was a beautiful day to sit outside and the deck area is really cute. I got fish and chips and they were delicious. I was worried it would be too heavy but it was the perfect portion and nice and crispy. My husband got a cheeseburger and I had a bite..it was delicious! He got a beer and enjoyed it too. I heard the server offer a family a kids menu so we will definitely be back with the kids.

We didn't stay after waiting for about 10 min to be acknowledged. Nice interior tho and several things on the menu that looked good. Just felt too impatient.

Ehhh... prices are a bit high; food was good but smaller portions, service was terrible. It's a craft brew "shack", with elevated food, not much seating and a staff that looks lost. Clearly, they hired a certain type of employee and it shows. Pherm, crooked crab and forward brewing have the same offerings with better service.

I have been a fan of RAR for many years and have visited the Cambridge location countless time. I was excited to hear about their new Annapolis location. The first week they opened, I happened to have an appointment around the corner and stopped in after to check them out. I forgot the exact time I was in but the place was already packed. It was way smaller than I anticipated it to be unless they have an upstairs or downstairs that wasn't open yet. Other than bar seating, they have long community tables so if you are a party of two, you will most likely be sat in between other parties. There is barely enough room to get in and out of your chair if someone is seated behind you. I had to get up a couple times for people to sneak through. The music was loud and my husband, two feet across the table, couldn't even hear what I was saying. The environment wasn't our thing the day we stopped by so we had a two beers and the drunken tots before rolling out. The tots were delicious and I definitely recommend them. We will try again some time in the future because I really want to love the place.

This is a fun place for lunch or after work. Great burgers and sandwiches and a wide selection of tap beers. I would like to see desserts added.

The food was average and the service was below average. But the drinks were good and the vibes are nice.

Went for lunch because I love their beer and have really enjoyed their spot in Cambridge. Very different experience in Annapolis, sadly. Burgers and chicken sandwich were small but tasty. Tater tots were quite good, hot and crispy. Onion rings were limp and flavorless and went uneaten. Crab balls were $16 for five balls the size of a quarter that had little to no crab meat and fell apart when you tried to pick them up. Basically they are outrageously expensive, crab flavored, poorly prepared hush puppies. In a seafood town like Annapolis this was appalling. Order came so slowly that we had to wolf it down and sprint back to work. Crab ball appetizer arrived as we were getting ready to leave. This place is not going to last long if they don't get their act together. Can't get away with food and service like this in Annapolis when lots of far better food options are close by.

Burgers and wings were just ok. Wings are small and burgers are pretty bland. For what you're paying, you're not getting your moneys worth in my opinion. Great atmosphere and beer, but food is only ok for the price.

Stopped by on Fathers Day we were seated very fast. The food was amazing, I got the lobster roll. Big pieces of lobster the roll was soft and warm with butter and old bay on the top. Best lobster roll I've ever had.

Food is really good, I had the pretzel bites ($11) and the veggie Chessie burger. Prices are not worth it though!! You have to pay $4 extra for beer cheese with the bites. And the burgers are tiny, for $14 too! And, that doesn't include fries or chips, gotta pay extra for those. Service is not good either. They're slow and we changed servers 3 times. Had to go to the bar to order another round of beers and the bartenders weren't any better. Rather rude if you ask me. Not sure if I'd go back

At Chesie's Wharf in Annapolis, my experience was truly exceptional, especially since I shared it with my mom. The atmosphere was lovely, complemented by the delicious craft beer and mouthwatering food. The steak sandwich, in particular, was a standout dish that left us craving more. The service was impeccable, making our visit even more enjoyable. I would definitely return to Chesie's Wharf for another memorable dining experience in Annapolis. Also McKenzie was our server and she was 10/10 See ya down the road!

Chessie's has a To Go ordering station that made it easy to place an order. The ambiance is open air and very nice on great weather days. Food was great!

I ate at Chessie's Wharf midday/midweek. I ordered boneless chicken wings which turned out to be deep fried balls of bread that may have had some chicken hidden inside. The garlic parmigiano dressing was dry cheese thrown on top after frying. Too salty and on the whole, barely edible. The service was excellent but the food menu was iffy and overpriced.

Hefeweizen is amazing. Have tried the wings, crab dip and drunken tots so far and everything has been delicious. Best spot in West Annapolis

The beer at this place is amazing. Definitely really pricey but the vibe and food options are amazing. Waiters were attentive and their beer selection has so much to offer from a bunch of local places. Their jam berry beer is THE BEST. Definitely recommend (make sure u bring some cash tho)

Excellent burgers but it's so loud inside that you can't hear yourself think. Very hard to have a conversation

Great time in a fun atmosphere! The loaded tots were delicious, and I highly recommend the burger!

Awesome! Get a flight of draft beers. Any food is great. Service is fantastic. Don't miss the singing fish on the hour.

Went right as they opened and got a nice seat. They have long community high-tops and a couple regular height 4-tops and bar seating. Smallish food menu but the burger was FANTASTIC!!! I ordered a double(only $2 more) with American/lettuce/Mayo and onion. Chose Mayo over the special sauce as I hadn't tried it. Next time the special sauce goes on! It's Mayo based, slightly tangy, slightly spicy. Nice to have a casual, beer and burger place in the neighborhood! We will be back. Service is good even as they got more and more crowded! By the time we finished our burger and onion rings(they were pretty good), there was no parking left and place was almost full up.

This place has great atmosphere and potential. Beer is good to mediocre. I'm glad to see they have a veggie burger option, but fries are optional. If you want a burger with fries, you're paying nearly $20. We had the crab empanada for an appetizer, and it was good, but it's basically a hot pocket. One. For $14. We've given this place two tries and it's just underwhelming. Food is absolutely overpriced.

The atmosphere and service were terrific. The food was super even our dog got a doggy burger. But, the beer was the real surprise. I loved the Blue Milk. I am sorry this was the weekend my son graduated from the Naval Academy. I will need to find another reason to go to Annapolis.

Annapolis has needed a place like this for a while now. The only close-ish alternative is Forward in Eastport. Love the open indoor/outdoor areas, great drink selection and the food was fantastic. Plenty of menu options, I got their jerk wings and tots - good serving size and worth the $. Staff was really friendly and going through the "in the weeds" stuff that any new place experiences, they were working their a** off. Do yourself a favor and check out Chessie's!

Went around 5:30 on a Tuesday. Place was small and has family style high top tables. A bit odd IMO. My husband and I were able to get a table, but the wait staff were not overly friendly. We had to ask for a food menu. We ordered a salad with grilled chicken, an order of wings and a fried chicken sandwich. All were mediocre and the prices were high. There were only about 10 wings and they were little and a tad over cooked. The Chessies Chicken sandwich was over cooked and small. Not worth $10. So, we were underwhelmed and not likely to go back. The best part of the night were the singing bass fish on the wall.

If you appreciate craft beer, this place is heaven on earth. The selection and quality of beers is incredible. Nobody else in the Annapolis area comes even close to Chessie's for its beer list. The food is excellent but, portions are modest and menu prices are not. The main problem is seating and this is why I would not return. Family-style seating can be fun but, the tables are so close together that no one can access or egress an interior seat without asking one or more people to get out of their seat to make room. I saw one guy who was so frustrated after being asked to make room 5 times that he smacked his metal tray across the table and walked out. If you sit on the end, you will have to get up and move your chair several times during a single meal during any reasonably busy period. The seating is essentially like a movie theatre where the whole row has to stand up in order to allow someone from the interior to walk out to the aisle. This situation would be easily remedied by moving the long family-style tables further apart. Until they do so, I will just stop by for their retail beer sales and forego the restaurant.

Food and beer are both excellent. Great atmosphere, only problem is it's very hard to get a seat on the weekends. If you can get a spot you'll enjoy it.