My new favorite place in town. Love this little hidden away gem where the service is great, the servers listen to what you ask for and deliver exactly what you wanted. Crispy bacon on my club? You’d be amazed how often I say that and get limp, chewy bacon. Not here. And price wise I think it’s one of the better deals in town for most items. Check it out…you won’t be disappointed.
Atmosphere: 5
Food: 5
Service: 5
Susan Kim
I did not expect such a fantastic lunch. All the good places in chestertown were closed for lunch so this seemed to be one of the few places open. I am so glad we went. The ahí tuna salad was as good as any I have had at upscale Baltimore restaurants. I got the Ruben sandwich without meat. Soooo good! And the club sandwich my mom got I heard was quite tasty. Our server was super professional. And the lighting was great. Not too bright or fluorescent. The only recommendation would be to have the fire going during lunch and not just dinner
Atmosphere: 4
Food: 5
Service: 4
Howard Gilson
For the last couple of years, we have spent most of September and October in the Chestertown area. Uncle Charlie's is one of our "go-to" places to eat. The food is well prepared, relatively inexpensive. The portions are large. The staff have always been more than great, like eating with family. Really enjoyed the crab mac and cheese, seared tuna salad, cioppino and the nachos. Only slight miss for me was the crab&pasta. While the parpadelle was great, I thought the pesto overwhelmed the crab and made the dish too heavy for my taste. Stop by. You won't regret it!
Atmosphere: 5
Food: 4
Service: 5
Chris Fleming
Just had probably one of the best burgers Ive ever had. It was topped with crabmeat and was perfect. Thank you Charlie for the wonderful meal!!!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Nachos
Beth Hart
Great food, friendly service & very good dining experience! Definitely recommend
This was the WORST LUNCH EXPERIENCE I CAN RECALL HAVING!!!! The service was EXTREMELY slow, the food was terrible. I grew up in Southern Maryland and had seafood during my time there. I enjoyed REAL crabcake cakes. As an adult, I have lived in the Midwest where good seafood is impossible to get. My Aunt had heard this was a great place for lunch, so we thought we would make a family afternoon outing of it. It took us two and a half hours to get there from Callaway, Maryland. While sitting there, still not having been attended to, two more customers came in, the server sat them. AFTER WAITING TWO HOURS, no exaggeration, the server FINALLY came to take our order. I, along with my sister, ordered the crabcake sandwich. Again, having had to wait a ridiculous amount of time for the orders to be served, my "back fin lump crab meat sandwich came all mooched together looking more like a breakfast cereal. I stopped the server to asked how the chef had prepared the crabcake, her reply, " If I tell you, I will have to kill you." then she went on her way. It was so bad tasting; I could not eat it. I ate the potato chips that came with the meal and that was my lunch! When my bill came, the server had charge me for Cole slaw that I had not ordered. She then tried to explain that she would just deduct the cost of my iced tea which cost less than the Cole slaw and it would be even. I had to tell her that was not correct. She would need to correct the bill and give me a new bill. We did finally get through with that experience and I shall NEVER do it again! A SUBWAY is in front of the business. You would be better served enjoying a SUB than eating there for lunch! It is VERY expensive. The sandwich, chips and tea cost me $28.00 without a tip!!!! No charge for all aggravation!!!!!
Rabbi Jessica K. Shimberg
We had a wonderful dinner and absolutely lovely experience once the owner seated us after expressing great dismay that we had failed to make a reservation. The service was excellent, our waitress was wonderful and the kitchen staff brought out delicious food. Crab dip appetizer was so good I would have licked the dish!! Caesar salad was OUTSTANDING (and I am a caesar salad snob); fresh and high quality romaine; clearly house-made dressing — perfect balance of ingredients, not too salty and could taste the anchovy and lemon. Other salad tasted was also excellent (ahi tuna salad). Dessert (key lime pie, made on the premises) was FANTASTIC. Rueben was the only disappointment—too salty and greasy and onion rings weren’t worth eating after such wonderful salad and appetizer.
Atmosphere: 5
Food: 4
Service: 5
Recommended dishes: Key Lime Pie, Salad
Allison Campion
We had pulled into town late and managed to find this restaurant.The staff was attentive, even a hour before closing, and very pleasant.We had a couple of appetizers and shared a sandwich. We left stuffed!
Atmosphere: 5
Food: 5
Service: 5
Zeda Ruhl
I only had dessert but I looked over the menu and I'm definitely going back! The restaurant is was and clean and the servers were very nice. I really liked that there is a fireplace that they light in the winter time.
The food was delicious. Everything was fresh especially the corned beef. My girlfriend loved her chicken sandwich. It was moderately busy but Emily managed it very well.
After trying to go to another local restaurant, where we were turned away because of being a 6 top...we found Uncle Charlie's.At Uncle Charlie's, we were greeted with open arms and sat immediately. Everything was amazing from drinks to dinner! The Washington Riesling was very nice...great peach notes and not too acidic. We had a variety of items: The delicious crab pasta, amazing shrimp scampi, Charlie's burger, Ahi Tuna salad with the best dressing ever, ceasar salad, onion rings and kid mozzerella sticks. We all finished every last bite!!Thank you to the staff for being so friendly! Emily was an amazing server, too!!Definitely recommend this treasure!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Burger Special with Onion Rings, Pasta & Crab, Salad
Sara D
This place was awesome. The food was great and very fresh. Homemade pasta and key lime pie. However you really have to find it off the street. Maybe bigger signage but thank goodness we came across it we highly recommend this restaurant. Excellent
Wes Vinton
Best burger I've had in a long time. Everyone I interacted with was incredibly friendly. Definitely coming back here in the future.
Atmosphere: 5
Food: 5
Service: 5
About Cupcakes
After trying to go to another local restaurant, where we were turned away because of being a 6 top...we found Uncle Charlie's.At Uncle Charlie's, we were greeted with open arms and sat immediately. Everything was amazing from drinks to dinner! The Washington Riesling was very nice...great peach notes and not too acidic. We had a variety of items: The delicious crab pasta, amazing shrimp scampi, Charlie's burger, Ahi Tuna salad with the best dressing ever, ceasar salad, onion rings and kid mozzerella sticks. We all finished every last bite!!Thank you to the staff for being so friendly! Emily was an amazing server, too!!Definitely recommend this treasure!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Burger Special with Onion Rings, Pasta
Russell Wallace
This restaurant is a very nice lunch or dinner option for those traveling on the Eastern Shore near Chesapeake Bay. The menu is the same as in many similar restaurants, but the recipes they use are different and very tasty. Trust your GPS to get you there. It's a bit hard to see from the road at the end of a tiny shopping center.
My new favorite place in town. Love this little hidden away gem where the service is great, the servers listen to what you ask for and deliver exactly what you wanted. Crispy bacon on my club? You’d be amazed how often I say that and get limp, chewy bacon. Not here. And price wise I think it’s one of the better deals in town for most items. Check it out…you won’t be disappointed.
Atmosphere: 5
Food: 5
Service: 5
I did not expect such a fantastic lunch. All the good places in chestertown were closed for lunch so this seemed to be one of the few places open. I am so glad we went. The ahí tuna salad was as good as any I have had at upscale Baltimore restaurants. I got the Ruben sandwich without meat. Soooo good! And the club sandwich my mom got I heard was quite tasty. Our server was super professional. And the lighting was great. Not too bright or fluorescent. The only recommendation would be to have the fire going during lunch and not just dinner
Atmosphere: 4
Food: 5
Service: 4
For the last couple of years, we have spent most of September and October in the Chestertown area. Uncle Charlie's is one of our "go-to" places to eat. The food is well prepared, relatively inexpensive. The portions are large. The staff have always been more than great, like eating with family. Really enjoyed the crab mac and cheese, seared tuna salad, cioppino and the nachos. Only slight miss for me was the crab&pasta. While the parpadelle was great, I thought the pesto overwhelmed the crab and made the dish too heavy for my taste. Stop by. You won't regret it!
Atmosphere: 5
Food: 4
Service: 5
Just had probably one of the best burgers Ive ever had. It was topped with crabmeat and was perfect. Thank you Charlie for the wonderful meal!!!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Nachos
Great food, friendly service & very good dining experience! Definitely recommend
Dietary restrictions: Low salt, heart healthy diet - met!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Nachos, Salad
This was the WORST LUNCH EXPERIENCE I CAN RECALL HAVING!!!! The service was EXTREMELY slow, the food was terrible. I grew up in Southern Maryland and had seafood during my time there. I enjoyed REAL crabcake cakes. As an adult, I have lived in the Midwest where good seafood is impossible to get. My Aunt had heard this was a great place for lunch, so we thought we would make a family afternoon outing of it. It took us two and a half hours to get there from Callaway, Maryland. While sitting there, still not having been attended to, two more customers came in, the server sat them. AFTER WAITING TWO HOURS, no exaggeration, the server FINALLY came to take our order. I, along with my sister, ordered the crabcake sandwich. Again, having had to wait a ridiculous amount of time for the orders to be served, my "back fin lump crab meat sandwich came all mooched together looking more like a breakfast cereal. I stopped the server to asked how the chef had prepared the crabcake, her reply, " If I tell you, I will have to kill you." then she went on her way. It was so bad tasting; I could not eat it. I ate the potato chips that came with the meal and that was my lunch! When my bill came, the server had charge me for Cole slaw that I had not ordered. She then tried to explain that she would just deduct the cost of my iced tea which cost less than the Cole slaw and it would be even. I had to tell her that was not correct. She would need to correct the bill and give me a new bill. We did finally get through with that experience and I shall NEVER do it again! A SUBWAY is in front of the business. You would be better served enjoying a SUB than eating there for lunch! It is VERY expensive. The sandwich, chips and tea cost me $28.00 without a tip!!!! No charge for all aggravation!!!!!
We had a wonderful dinner and absolutely lovely experience once the owner seated us after expressing great dismay that we had failed to make a reservation. The service was excellent, our waitress was wonderful and the kitchen staff brought out delicious food. Crab dip appetizer was so good I would have licked the dish!! Caesar salad was OUTSTANDING (and I am a caesar salad snob); fresh and high quality romaine; clearly house-made dressing — perfect balance of ingredients, not too salty and could taste the anchovy and lemon. Other salad tasted was also excellent (ahi tuna salad). Dessert (key lime pie, made on the premises) was FANTASTIC. Rueben was the only disappointment—too salty and greasy and onion rings weren’t worth eating after such wonderful salad and appetizer.
Atmosphere: 5
Food: 4
Service: 5
Recommended dishes: Key Lime Pie, Salad
We had pulled into town late and managed to find this restaurant.The staff was attentive, even a hour before closing, and very pleasant.We had a couple of appetizers and shared a sandwich. We left stuffed!
Atmosphere: 5
Food: 5
Service: 5
I only had dessert but I looked over the menu and I'm definitely going back! The restaurant is was and clean and the servers were very nice. I really liked that there is a fireplace that they light in the winter time.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Jicama Slaw, Lamb Shank, Chocolate Covered Strawberry Cheesecake, Crab Bruschetta, Diet Miller, Uncle Charlie
The food was delicious. Everything was fresh especially the corned beef. My girlfriend loved her chicken sandwich. It was moderately busy but Emily managed it very well.
Atmosphere: 4
Food: 5
Service: 5
Restaurantji Recommends
After trying to go to another local restaurant, where we were turned away because of being a 6 top...we found Uncle Charlie's.At Uncle Charlie's, we were greeted with open arms and sat immediately. Everything was amazing from drinks to dinner! The Washington Riesling was very nice...great peach notes and not too acidic. We had a variety of items: The delicious crab pasta, amazing shrimp scampi, Charlie's burger, Ahi Tuna salad with the best dressing ever, ceasar salad, onion rings and kid mozzerella sticks. We all finished every last bite!!Thank you to the staff for being so friendly! Emily was an amazing server, too!!Definitely recommend this treasure!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Burger Special with Onion Rings, Pasta & Crab, Salad
This place was awesome. The food was great and very fresh. Homemade pasta and key lime pie. However you really have to find it off the street. Maybe bigger signage but thank goodness we came across it we highly recommend this restaurant. Excellent
Best burger I've had in a long time. Everyone I interacted with was incredibly friendly. Definitely coming back here in the future.
Atmosphere: 5
Food: 5
Service: 5
After trying to go to another local restaurant, where we were turned away because of being a 6 top...we found Uncle Charlie's.At Uncle Charlie's, we were greeted with open arms and sat immediately. Everything was amazing from drinks to dinner! The Washington Riesling was very nice...great peach notes and not too acidic. We had a variety of items: The delicious crab pasta, amazing shrimp scampi, Charlie's burger, Ahi Tuna salad with the best dressing ever, ceasar salad, onion rings and kid mozzerella sticks. We all finished every last bite!!Thank you to the staff for being so friendly! Emily was an amazing server, too!!Definitely recommend this treasure!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Burger Special with Onion Rings, Pasta
This restaurant is a very nice lunch or dinner option for those traveling on the Eastern Shore near Chesapeake Bay. The menu is the same as in many similar restaurants, but the recipes they use are different and very tasty. Trust your GPS to get you there. It's a bit hard to see from the road at the end of a tiny shopping center.
Atmosphere: 4
Food: 5
Service: 5
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