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Old Barn Brewery

4.0 (1 review)
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8 months ago

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Chessie’s Wharf

Chessie’s Wharf

(87 reviews)

$$

My wife and I were looking to try something new in Annapolis and came across Chessie's Wharf on…read moreYelp. When we arrived, it was pretty busy. All the outdoor seating was full, and inside there was only one table available. Most of the tables are larger, so we noticed some groups sharing space, which actually worked out fine. The restaurant has a great open-air feel even indoors thanks to the large garage-style door that opens up an entire wall. For drinks, my wife ordered iced tea and I had a Peach Mule. The mule was good, but next time I'd skip the rim garnish. They also have a big beer selection, and the prices seemed very reasonable. For food, we ordered the brisket burger (single patty with cheese, topped with shaved brisket, jalapeño slaw, raw onion, pickles, and sauce). They offer a deal where you can add a side and drink for $5, so we added onion rings and also ordered the Serpent Fries as an appetizer. The fries came out first and looked great and they did not disappoint. Fresh cut with bacon, pico, scallions, and a serpent sauce (seemed like a beer cheese). Really flavorful, I did ask for ranch, which was an extra $0.50. I understand charging for extras, but not everyone uses ketchup or mustard, so that felt a little unnecessary. The burger came out shortly after, and it was excellent. We split it, and it was packed with flavor. Honestly, adding bacon would make it even better a "Triple B" (Bacon, Brisket, Burger) would be perfect. The only letdown was the onion rings. The onions inside were very thin and overcooked, leaving them dried out with little flavor. Even without the over-frying, the onions themselves just didn't have much taste. Definitely something they could improve. Overall, it's a great spot for burgers and fries, and we'll definitely be back for that. We saw other dishes come out that looked good too, so there's more to try next time.

BLUF: RAR beer and bar eats like burgers and tots with minimal parking…read more What I love about Chessie's Wharf is that it plays on the local lore of Chessie the Sea Monster. Also, the decor is great and the tap line is long. Aside from RAR beers there are a few rotating handles with beer from "guest" breweries. But no need to venture out to guest brews, RAR has great selections. If you're not a beer drinker they also have spirits and seltzers. I'm not sure about wine but I suspect they have a few options. Foood selections are comforting and simple - mostly burgers, wings, fries, tots and salads. For slightly more special options they have a brisket burger, crab dip and a few other tantalizing selections. I'll gladly work my way through the whole menu. I love that they brand Chessie into the buns. So cute! Chessie's has bar seating and lots of community tables so introverts be aware. When the weather is nice they have a great patio. To relive the memories of this great neighborhood bar, they sell merch and canned beer.

Preserve - Pork Terrine

Preserve

(500 reviews)

$$

At Preserve, consistency is not the point, evolution is. Each visit feels slightly different,…read moreshaped by a menu that shifts with the seasons and refuses to coast on familiarity. That restlessness works in its favor. The space is compact, almost disarming at first. Then it settles around you. There is a quiet intimacy to the room, the kind that feels less designed and more lived in. It leans closer to a welcoming home than a polished dining room, without losing its sense of purpose. The food carries that same balance. Thoughtful, seasonal, and just unpredictable enough to keep you paying attention. Cocktails follow suit, measured and deliberate, never an afterthought. For Annapolis, where good options are not exactly rare, this place still manages to separate itself. It belongs firmly in the top tier of the city's dining scene, and it earns that position every time it changes the menu and starts over again.

Located on Main Street with bar, inside/outside seating. Wonderful decor and a great drink menu…read more Food menu was great as well and not too overwhelming. This is a place that has lots of drinks and foods that have some unique and creative flavor profiles. We were greeted immediately and sat at bar. Server acknowledged us quickly and was very friendly. Checked on us throughout the time we were there. Ordered a tequila cocktail that was amazing. Highly recommend!!! So so good. Their cocktail menu has the spirit and then a description under of the drink. No actual names. Lots of interesting drinks. We grabbed a couple of apps. Got the pork bites and smoked fish dip. Both were tasty and had interesting flavors that worked. The portions were great. You can tell that great care and thought is put into to the menu. The burger and fries looked amazing - on special and lots of people around us were ordering it. Would have ordered that if we were eating a bigger meal. This is a gem of a place. Truly crafty food and drinks. Highly recommend trying them out. Would come back again.

Adams on Fourth - Really yummy sweet potato casserole

Adams on Fourth

(32 reviews)

The Good: location, ambiance, staff, speed The Not So Good:…read moreThe food. We got the crab and artichoke dip, the brisket tacos, the arugula salad, and a burger. The best items were the arugula salad (fresh and a good value), the fries (fresh), the burger bun, and the bread that comes with the crab cakes. The crab dip had good flavor but the portion felt v small for an appetizer and not a single piece of legit crab meat. In Maryland the crab dip has at least a couple real pieces of meat. The burger was...fine. They charge extra for cheese. The real tragedy was the brisket tacos. The brisket was DRY, overdone, and near flavorless. It almost seemed like it had been sliced and then reheated. The bourbon sauce was so sweet, like maple syrup. And the "coleslaw" was equal parts cabbage, raw onion, and green pepper. Weirdest coleslaw ever. So the tacos ended up tasting like maple syrup covered onions. I have literally never in my 39 years of life sent something back, but I sent those back. It was inedible. The waitress was super nice and sweet about it and took it off the bill, so there's that. We gave it 6.5/10. We might go back for the nice clean open space if one of our friends wanted to go there, but with soooo many restaurants around it's unlikely we would seek it out again.

Love coming here! Probably frequent this establishment a few times a month! Had dinner with the…read morefamily/cousins last night here and we had a great time! I had a soup and a salad. Can't go wrong with the French onion soup! Also indulged in an Aperol spritz, which was very yummy! We sat upstairs because we had a big crew and it was nice because we could still see the tvs at the bar and watch the playoffs.

Old Barn Brewery - breweries - Updated May 2026

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