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    Osprey Point Restaurant

    4.5 (49 reviews)
    PriceySeafood, Salad, Soup
    Closed Closed

    Osprey Point Restaurant Photos

    OSPREY POINT RESTAURANT ATMOSPHERE

    What's the vibe?
    Quiet
    Classy
    Good for groups
    Outdoor seating

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    Sherine And David G.

    My husband took me there for Valentine's week end this year. We stayed for 3 nights. He booked us a gorgeous room, "the Escapade" that has breathtaking views of the Chesapeake Bay. The service: let me emphasize with vigor how far above and beyond the folks at the Osprey Point Inn go to make their guests happy. They have been bending over backwards to make our stay the best it could possibly be since the night of our arrival, always going the extra mile, always managing to surprise us with a thoughtful gesture. On a scale from one to ten, I give the service a 20. The restaurant: I'll say it flat out, the Inn's restaurant is the best restaurant of the area. I am a total foodie, I am from a long line of older foodies, and everyone in my family cooks, which makes me a pretty tough food critic. We have been dutifully sampling the local fare at other restaurants in the area, none of them even come close. Their Executive Chef, Matt Whitehair, is managing to be inventive and stay fresh in his approach to classics, while still staying true to what made them classics in the first place. The dishes are therefore never boring, while still maintaining their "comfort" factor. The main ingredient always shines, showcased by its accoutrements, but never lost in them. His tea smoked seared scallops are divine, and I seriously advise you to try them if you are in luck and they are on the menu. We are having dinner there again tonight, and I'm already looking forward to trying his lamb (served with a pear puree, glazed carrots and fingerling potatoes, and complemented with a gastrique reduction , if you please...). I also want to point out that I have a medical condition that forbids me to eat any type of nuts or seeds, and that the Chef himself took the time to accommodate the Valentine's menu to make my dining experience as good as it could be. In a nutshell, if you are in the area and want to have a seriously fantastic dinner, go to the Osprey Point. If you are not from the area and are looking for a comfortable romantic getaway where you can enjoy your wine and have a fine dining experience without having to worry about driving back to your hotel, go to the Osprey Point. Basically, just go to the Osprey Point.

    Wintry landscape overlooking the marina.

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    1 year ago

    Our table for six was ready on time. Food and service were excellent. Beautiful location. We will be back!

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    1 year ago

    We enjoyed the lovely ambiance, the wonderful service and excellent food! We will definitely be back again.

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    Great meal, good service, nice ambiance. Enjoyed by all ages. It was great for mom's birthday dinner!

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    Page 1 of 2

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    Review Highlights - Osprey Point Restaurant

    After a nice ramble through some of the very quaint shops, we headed back to the Inn to stow luggage, etc.

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    Harbor Shack - Mussels Alfredo

    Harbor Shack

    3.7(87 reviews)
    0.6 mi
    $$

    Touted as the locals place to eat, it is fabulously divvy! We had good service and enjoy dining on…read morethe 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.

    Nothing makes you less likely to return to work after lunch than sitting at one of their dock…read moretables, munching down a great lunch and staring at the variety of ice cold beers. prompt friendly service, but I sensed being "off season" gave us the best experience. Prompt refills on drinks. 8 of us ate, everything from crab cakes to club sandwiches were fresh and tasty. Fries had a clean cook to them , crisp but not over cooked. Solid but not stellar value.

    Photos
    Harbor Shack - Situated on the harbor the covered decks face the boat docs. Inside dining is also available.

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

    Harbor Shack
    Harbor Shack - Dock view

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    Dock view

    The Retriever Bar and Oysters - The House Burger

    The Retriever Bar and Oysters

    4.3(37 reviews)
    10.9 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.

    Photos
    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

    Osprey Point Restaurant - seafood - Updated May 2026

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