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    Old Barn Brewery

    4.0 (1 review)
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    9 months ago

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    Chessie’s Wharf

    Chessie’s Wharf

    3.9(89 reviews)
    3.4 mi
    $$

    I had no idea this place existed til a coworker of mine selected this place to go on his last-day…read more Such a cute, clean place to come - with an even better happy hour menu! The staff was super attentive, frequently asking if we needed anything or if our cups or plates needed to be replenished. I would love to return for some of their locally-brewed beer and IPAs as well. Pictured with my review, you'll see my margarita from where I sat at the bar, and happy hour meal, the boneless chicken wings and fries. This place was the perfect place for an office farewell!

    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.

    Photos
    Chessie’s Wharf - Inside seating

    Inside seating

    Chessie’s Wharf - Espresso martini. Very good with whatever ice cream they used.

    Espresso martini. Very good with whatever ice cream they used.

    Chessie’s Wharf - Brown and a Hazy. Both excellent.

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    Brown and a Hazy. Both excellent.

    Crooked Crab Brewing Company - The cold brew and the pizza from elsewhere

    Crooked Crab Brewing Company

    4.4(214 reviews)
    12.4 mi
    $$

    I'm in Maryland, how can I not hit a brewery called CROOKED CRAB?!?…read more Pizza was on the menu... crisp thin crust and plenty of toppings. Beer was great, and I tried quite a few! Backfin was my favorite, I'll have to come back!

    I wanted to enjoy this place especially off the strength of two colleagues along with the reviews…read moreraving about this place. I will break it down with pros and cons. Pros: Great variety of beers on tap hefty pours on the tasting package Regulars come here to hang Plenty of seating Extremely chill...we brought a game and were able to play while we enjoyed our drinks Cons: If you have dietary restrictions you will starve; I have a gluten allergy and could only order the wings as the menu is limited to one brisket sandwich, wings, or pizza. They also did not have gluten free or cauliflower crust Many of there beers on tap are not updated on the menu so unless you inquire with the staff you will not know as I ordered a mead that was not included on the menu This is a self serve place, you go up to order and they bring it out to you I will not go out of my way to visit again as we left hungry and then had to make another stop; however if in the area would return again. if ocmpared to Jailbreak Brewery I would choose jailbreak everytime.

    Photos
    Crooked Crab Brewing Company - Inside right

    Inside right

    Crooked Crab Brewing Company - Pep n' step pizza - Smoked mozzarella, house made red sauce, beef pepperoni, cupping pepperoni, jalapenos, red pepper flakes, hot honey

    Pep n' step pizza - Smoked mozzarella, house made red sauce, beef pepperoni, cupping pepperoni, jalapenos, red pepper flakes, hot honey

    Crooked Crab Brewing Company - Crab Cannon is good! I'm at the bottom.

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    Crab Cannon is good! I'm at the bottom.

    Preserve - Pork Terrine

    Preserve

    4.3(502 reviews)
    4.0 mi
    $$

    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.

    We had made a reservation here for a Sunday brunch at 11. It wasn't overly busy when we came. This…read moreis in downtown Annapolis so there's some street parking around. Bright and open inside with friendly service. We ordered a handful of mimosas and got a couple of small bites to share. Sourdough Foccaccia - this was pretty good, warm and toasted. Pork Bites - I loved the flavor but thought this was pork belly and not ground pork. Overall, flavor was good but the texture wasn't great. Crispy Kale - this is very popular here and we really enjoyed it. The cumin yogurt really brought it together. Pickled Squid - Not what we expected but I actually really liked this dish. We did also order the Coconut Panna Cotta for dessert. The raspberry was pretty prominent here and wasn't as custard like as expected, just a little too soft but the flavor otherwise wasn't bad. Overall, everything was pretty good and I would visit again to try other items on their menu.

    Photos
    Preserve - Seating

    Seating

    Preserve - Fish Dip

    Fish Dip

    Preserve - Bar area

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    Bar area

    Cheers & Spirits - Official Logo

    Cheers & Spirits

    2.5(16 reviews)
    1.6 mi
    $$

    Bottom Line: Decent selection with some cool business ideas but service is lackluster…read more I'm desperately searching for my new go-to liquor store - the kinda place where you go every week and the staff recognizes you and offers a warm hello. I started my quest with Cheers & Spirits since they are so close to where I live and run coupons on the back of my Safeway receipts. I was able to find both beer and wine that peaked my interest so that was good. (I did not check out the liquor selection.) Where this store left me disappointed was with the customer service, or lack thereof. I guess I am old fashioned because I still have false hopes that store staff will say hello and offer assistance. Despite being the only person in the store, there was little service to be had. One employee had their head down distracted by their paperwork. Eventually, another staff member did come offer assistance when he saw I had my arms full (literally). I tried to engage him in conversation about various craft beers but he either didn't know the product or didn't seem too enthusiastic to talk shop. I'll give Cheers & Spirits another try because all businesses have their off days, but I'll also keep looking for my new go-to spot.

    Under new owner & management! C&S is in a great locations with plenty of parking & has a great…read moreselection of wines and spirits. Staff was very helpful. I'm glad there's been a change.

    Photos
    Cheers & Spirits
    Cheers & Spirits
    Cheers & Spirits

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    Old Barn Brewery - breweries - Updated May 2026

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