Dempseys Grille

A great diner in the heart of Middletown. The club sandwich and roast beef were great. I will definitely be back.

They have a shrimp salad in season that is a mouth experience. The beef vegetable soup is a must according to granddaughter. Also love Reuben, corn fritters & fried chicken. True homemade comfort food. Only complaint is they’re only open till 2pm on Sat, Sun & closed on Monday. Might have to stop for breakfast on our way home in WA state.

Great home cookin friendly folks. I enjoyed my meal greatly. Enjoy the small town environment. I didn’t feel like just a customer I was extremely welcomed. Will come back often.

Took my son here for a quick bite for a Saturday morning breakfast. Service is down-​home friendly, food is good diner food, and it is all set in a great small town.
My son couldn’t figure out what he wanted; when he did, it wasn’t on the menu, but the waitress hooked us up and made him an al-​a-​carte style breakfast.
My go-​to breakfast spot.

Our favorite place to run in for a meal. It is always like eating with family. If you’ve been out mowing or just stepped out of the spa, you’re always welcome at Dempsey’s. The food is cooked to order right in front of you. The soups are home made and better than any place in town. The portions are generous and the prices are reasonable. They have had the same staff there for years and they know all of their customers and their likes and dislikes. Good food, comfortable people, there’s not much better than that.

The family decided to go out for lunch on our way to South Mountain Creamery. Based on other reviews we stopped and were pleased with the experience. We had Rubens, Crab Cake sandwiches, Corn Fritters and Tater Tots. The Ruben was nicely grilled, plenty of sour kraut, light dressing and great/​lean beef. Crab cake sandwich was the right kind, not killer crab, but on a sandwich it doesn’t have to be. Loved the powered sugar on the Corn Fritters. Lunch for 4 for under $ 50 including tip. Great friendly service to boot.

This place is a great place to get a home cooked meal. I love their steak and cheese sub. with grilled onions and peppers. It’s right up there with Pat or Ginos steak and cheese in Philly.

Stopped in to grab a quick lunch. I had a cup of the beef veggie soup and a turkey bacon Swiss sandwich. Both the soup and sandwich was great. My gf had their tomato basil soup with a grilled ham and cheese. Their tomato soup was amazing! Best I have ever had hands down. Both of us ate for $ 25 and that includes tip! Definitely recommended! Good food at a low price.

This place was what I was looking for. A small town diner with great tasting food and good prices. The staff was friendly and the service was quick for what I expected. We will be back for sure

My favorite place. The soups are amazing, The breakfast is amazing. The desserts are– you guessed it– amazing! The staff is friendly, the place is clean and the prices are reasonable. Everything you’d want in a good place to eat!

Thursday night’s special chicken parm and Italian night. Chicken parm and homemade sauce excellent. Wife had the softshell crab and crabcake club, which was the special for the week. Outstanding! Staff is over the top friendly, and prices lowest in the county. I love how the owners are the cooks and really provide a great atmosphere. Staff is tenured which they seem to have low turn over. I hear the breakfast is terrific with low prices and no gimmicks…

Middletown is Lake Woebegon in central Maryland. You really can’t ask much more for a hometown experience than an authentic greasy spoon like Dempsey’s. The food is full-​on American comfort. You’ll find the place packed in the early morning and at the lunch hour on weekdays and weekends.
They do breakfast really well but their cheesesteaks and homemade chili are out of this world.
Let’s face it though. We like the food but we really like the cozy feeling the venue and the staff engender in us. The staff is genial and friendly and the owners are usually working alongside their employees. Mike and Sybele, you’re the bomb!

As diners go, this is a good un! Can’t beat CHEAP slightly greasy food on a historic main street. The desserts are a must.

(10/​30/​2013) Good, basic, little diner on a quaint main street in a rural town. Open early for breakfast, serves the standards. Wandered in around 10:30 am on a weekday, grills already switched over from breakfast to lunch. Started with a cup of the Chicken and Corn Soup (like classic chicken noodle with lots of dried parsley and canned corn); chicken-​y well-​salted, but not salty, some coagulated proteins in the broth, chock full of lots of shredded chicken breast and curly wide egg noodles. Had a Grilled Reuben, piled thick with salty decent quality corned beef, 2 slices of Swiss and plenty of Thousand Island dressing. Sandwich was griddled pale golden and came very quickly, maybe too quickly, some parts of the sandwich were stone cold, parts of the cheese were not melted. Overall, good value, mostly friendly (some paranoid vibes when I took a few snaps, maybe that’s unusual out here, or maybe I just don’t look like I’m from around these parts).

Stopped in for a hot soup on a rainy day. Service was unbelievable and soup was good for a country diner.

My whole family has been coming here for years, even before it turned into Dempsey’s Grille. The staff is always great and you feel like you’re at home. I have never gotten a bad meal there. Sometimes the wait is a little long but for the food quality it is definitely worth it. Homemade cakes, pies, etc. as well and you can’t go wrong with any of those.

What can I say? I got kids. You got hash browns. We were meant to be.
And the homemade chili ROCKS!

What a great find in Middletown!
Ever go to a diner where everything seems from a can … salty … lame? Right. How about the OPPOSITE? Great mushroom and onion gravy on your fresh mashed potatoes … awesome chili and homemade beef vegetable soup … etc etc etc
Will certainly be back …
PS I fixed up the Unilocal!listing so hopefully more folks will stumble across this great joint.

Oh, I love Dempsey’s. Classic «Main Street America» diner, with yummy food that always tastes homemade. Delicious iced tea. When I was pregnant I used to walk there just to get an iced tea (to-​go), then walk home. I love it. «Let’s go to Dempsey’s for Breakfast» is music to my ears. If you go in a couple of times, the staff will start to remember you, they might even have an iced tea sitting at your table before you sit down :-)
Great small-​town service. Unassuming, unpretentious, and you can watch Main street roll by the windows while you eat.

Best chicken salad i have had in a long long time. Very friendly staff and nice local atmosphere.