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Harbor Shack

3.7 (87 reviews)
ModerateMexican, Seafood
Closed • Closed
Updated 3 months ago

Harbor Shack Photos

HARBOR SHACK ATMOSPHERE

What's the vibe?
Casual
Very loud
Good for groups
Outdoor seating

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Recommended Reviews - Harbor Shack

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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.

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.

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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15 years ago

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10 years ago

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12 years ago

Great find! Enjoyed bacon, spinach salad w blackened chicken and crab cake sandwich. So relaxing and beautiful view.

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13 years ago

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11 years ago

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12 years ago

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The Retriever Bar and Oysters - The House Burger

The Retriever Bar and Oysters

4.3(37 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.

Fantastic dinner experience at The Retriever Bar during our Chestertown getaway! We popped in while…read morestaying at Brampton 1860 and loved it. The House Burger was cooked exactly to perfection. We also tried the shrimp & grits, which arrived beautifully plated. We couldn't resist splitting the apple strudel for dessert, topped with locally made ice cream from Stams. Special shoutout to our server Kassie, who went above and beyond with her hospitality and gave us some great tips for things to do around Chestertown. The bar area has a great atmosphere too. We'll definitely be back on our next visit to Brampton to try more.

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The Retriever Bar and Oysters - The bar

The bar

The Retriever Bar and Oysters - Apple strudel

Apple strudel

The Retriever Bar and Oysters - Shrimp & Grits

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Shrimp & Grits

Harbor Shack - mexican - Updated May 2026

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