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    Harbor Shack

    3.7 (91 reviews)
    ModerateMexican, Seafood
    Open • 11:30 am - 8:00 pm

    Harbor Shack Photos

    HARBOR SHACK ATMOSPHERE

    What's the vibe?
    Very loud
    Casual
    Happy hour specials
    Outdoor seating

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    Recommended Reviews - Harbor Shack

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    Situated on the harbor the covered decks face the boat docs. Inside dining is also available.
    Debbie M.

    Touted as the locals place to eat, it is fabulously divvy! We had good service and enjoy dining on the deck that overlooks the marina. I ordered the Red Grapefruit Crush, which was very refreshing and delicious. Since we are in Maryland, we ordered the crab dip appetizer. It was creamy and is served in a bread bowl that you break apart to eat. It is a mess eat, but the dip is creamy and delicious. It has an undercurrent of sour cream or maybe cream cheese and it plenty to share with others. My husband had the fried shrimp for dinner with the veggie of the day, local corn on the cob. He said it was crispy and very good. I ordered the Maryland crabcake which was flaky with crab and I had a salad and the corn as well. All of it was prepared perfectly, came out quickly, and was sized perfectly. For dessert we shared the hot apple tart which is served with creamy cinnamon ice cream. Yum! Highly recommend Harbor Shack.

    Crab dip
    Ric T.

    This is a waterfront restaurant with a great open atmosphere. Stephanie and her mini crew were very accommodating. Good beer, great seafood, especially the crab dip and good discussion made this a very nice evening. There's also a gift shop and plenty of parking. Very casual dress.

    a plate of salad and a drink
    Valerie S.

    My husband and I had lunch at Harbor Shack last summer with some friends. The restaurant is comfortable and welcoming and right on the water. The service was fast and friendly. The food was great (I had a really good steak, mac and cheese and salad), and the rum buckets were even better. I loved the cute little store across the parking lot as well. We usually go to Waterman's when we're in Rock Hall. I think I will push for Harbor Shack next time as it just had a newer and more laid back vibe to me.

    Chicken bacon ranch sandwich
    Puppycat U.

    Great service, food was very good, do recommend the chicken sandwich if you come here. All the locals love going here so you know that this is the spot

    Pepsi cravings
    MaryLou B.

    Gorgeous place!! Inside under the roof in this open floor plan... no walls so there was a beautiful cross breeze! The staff is personable and have happy faces. No rush, casual atmosphere... almost feels like I'm on vacation!!! Ms Kay and Stephanie really make you feel like I'm having dinner at my family's house, kinda like a family reunion (except I have never been here). The crowd seems like it is hometown locals hangout type. Push some tables together and it's a family seating. We were a party of 9! And we had NO wait!!! We called ahead and Ms Kay said it would only take 10 minutes to get the table ready! We got there and it took less than 2 minutes! All the dishes were on point! So flavorful and savory! Huge portions! We all shared and did a tasting tour and there was smiles all around the table!!! I wish I could take this place to my town!!! It was a memorable experience :)

    Crab cake

    This place is really good I really enjoyed the crab this is a place that I recommend to others coming to rock hall

    Waterfront at Harbor Shack

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    11 months ago

    Great meal and great service! Had a delicious burger and quesadilla! Will be back again!

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    1 year ago

    What a great way to celebrate spring! Great food, drinks and service. Happiness on a cloudy day! Chris

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    2 years ago

    Great local hang out. Waterside draws in travelers. Good food., great service. All the staff enjoy their work

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    3 years ago

    Excellent! Food (soft shell crab) drinks, and service (bartender)! So happy that we stopped there!

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    4 years ago

    Lively atmosphere and great service! There is nothing sleepy about this joint. Great selection of daily specials. Will return!

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    Blue Heron Oyster House & Inn

    4.4(44 reviews)
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    Friday evening, we arrived for a later dinner and we were immediately greeted by the hostess and…read morewere seated within a few minutes. We started with the flavorful and lightly crispy Thai chicken tenders. We will order these again! My husband ordered the prime rib, of which I had a taste, and it was delicious! I ordered the crab cake dinner and it was tasty. We enjoyed the nice choice of rice or 3 kinds of potato. We did decide to splurge with dessert. The flourless chocolate cake was so yummy and my husband's bread pudding smelled, and apparently tasted, just like fall. It is not your traditional bread pudding, but a wonderful dessert nonetheless. The restaurant is nicely decorated for this Chesapeake Bay community. It can get quite lively and while there are acoustic tiles on the ceiling, it was hard to talk until the dining room was only about half full.

    We've been coming to Blue Heron since it opened. We loved the food, the ambiance, and the service…read moreis consistently good, although quite slow on weekends. Our last few visits have been disappointing. They took the oyster po boy off the menu (one of our favorites!) and the portions have gotten smaller, not as tasty and pricier. Must also mention that the hostess - face of the establishment, should try to smile. I appreciate it must be difficult to deal with hungry patrons for hours, but still..

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    Maryland Crab Soup (not much crab, but tasty)

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    The Retriever Bar and Oysters - The House Burger

    The Retriever Bar and Oysters

    4.3(40 reviews)
    11.0 mi

    The Retriever Oyster House in Chestertown left us with a mixed impression, one that deserves a fair…read moreand constructive take. We had just come from a college football game and, on the fly, decided to grab dinner here based on the recommendation of the one local in our group. There were seven of us, and most went for the double smash burgers with fries, which were excellent. Kim, our server, was outstanding, prompt, accurate, and attentive throughout the evening. The bartender also added to the positive side of the experience, making sure everything at the table ran smoothly. The issue came at the door. We had tried to call ahead to let them know we were on the way, not realizing that OpenTable was their preferred system. When we arrived, the host made this clear, but in a way that was unnecessarily sharp and cold. It set the wrong tone for the night. In a town where friendliness is the norm, the contrast was striking. The experience began under a haze that was difficult to shake, even though the food and drinks were excellent once we sat down. To be constructive, this is less about policy and more about hospitality. A host sets the tone, and a welcoming explanation could have changed everything. Something as simple as, "We usually use OpenTable to handle groups this size, but I'm glad you're here, let's get you taken care of," would have gone a long way. Instead of frustration, it could have created a positive first impression and likely earned a loyal group of returning guests for years to come. Inside, the atmosphere was lively, with locals enjoying themselves in a loud and fun environment. Our group of longtime friends who have been convening in Chestertown for two decades fit right in once we were seated. However, the bad first impression lingered, and as a result we only had one round with food before deciding to leave a lot earlier than our normal rhythm for an evening out. We ended up taking our bar bill to another venue. Great food and excellent table service carried the night, but the host made sure we will not be returning as part of our annual tradition. This is a restaurant with strong potential, and it could go from good to exceptional with just a little more attention to how guests are greeted.

    This was a fun place. We came visiting friends while in town for the Tea Party weekend, so they get…read morea little pass for being busy. I'm not sure the menu was all that imaginative, but the food was good and we enjoyed some oysters, onion dip, and I had the chicken sandwich. Our waiter was very attentive. The only thing I may add is to think about better flexibility on seating. It's a very large bar but the sit down area isn't greatly configurable. We'd put in for a group of 6 but it was not possible for them to seat us all at one table.

    Photos
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    Harbor Shack - mexican - Updated October 2026

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