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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?
    Classy
    Quiet
    Outdoor seating
    Good for groups

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    Recommended Reviews - Osprey Point Restaurant

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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

    Ask the Community - Osprey Point Restaurant

    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.”

    Mentioned in 16 reviews

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    Blue Heron Oyster House & Inn - Oyster sampler

    Blue Heron Oyster House & Inn

    4.4(44 reviews)
    0.3 mi

    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..

    Photos
    Blue Heron Oyster House & Inn - Maryland Crab Soup (not much crab, but tasty)

    Maryland Crab Soup (not much crab, but tasty)

    Blue Heron Oyster House & Inn - Crab Meat Centerpiece Appetizer! We drive 2 hours just for this!

    Crab Meat Centerpiece Appetizer! We drive 2 hours just for this!

    Blue Heron Oyster House & Inn - Lemonade very refreshing

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    Lemonade very refreshing

    The Retriever Bar and Oysters - The House Burger

    The Retriever Bar and Oysters

    4.3(40 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.

    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
    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 September 2026

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