I was in town for a wedding on a Sunday and was looking for some quick cheap food to bring out while a couple of us were helping set up the wedding venue. Saw that this diner had a good looking menu so decided to come out and give this place a shot. Many of the food options were super cheap! The service was attentive and kind as well. I ordered a bagel with cream cheese and country ham and American cheese, and my boyfriend got their 6 inch roasted beef sub. Both were pretty reasonably sized sandwiches and we enjoyed eating it as both were flavorful and tasty. My boyfriend's sub also came with chips. All in all, was quite satisfied with our meal! read more

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A nice diner after a weekend camp or hike. Service was fast and friendly. Food was fine. A little pricey for what you are getting ($4.50 for a single waffle) but it hits the spot. I'd come again. Clearly a popular little local spot. It was 80% full Sunday morning when we stopped by. Coffee was okay, mug kept full. read more

Dempseys Grille - Belgian waffle (with a lot of butter) -$4.45 - Diners Near Me - Middletown, Maryland

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Yep it's a breakfast spot lunch and dinner on the weekends Food is great coffee is hot and taste good Iscrapple and they cook it right and it's the best Rappa ! The wait staff is friendly and attentive Just go it's good read more

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We stopped on our way from W VA to Baltimore at about 10 am on a Saturday morning. Apparently this is one of their busiest times. Nevertheless we were seated and greeted within 5 minutes by a very friendly waitress. read more

Dempseys Grille - Weekend after Thanksgiving - Diners Near Me - Middletown, Maryland

This is such a cozy small town diner which is what makes it worth going here. The food is really good but certainly not a place where you watch your calories. The staff are always friendly and the way the diner is set up you end up talking to the other diners near you. These are some of the things that make up the charm. Breakfast is a go to favorite for us here. If you are looking for a home town dining experience, I highly recommend you try this place out. read more

Such a cute and whimsical establishment! Their staff is so kind and breakfast there sets the tone for the day.

Great atmosphere. Not a big place but the food is very good. Great presentation of the their food.

What a quaint hometown setting! We had such a great experience on a day that those who were working there might not have seen it the same way. They were having a very busy, difficult rush. Things were getting overwhelming fast! My husband and I watched a fairly young group of staff join together and turn things around by working harmoniously together! It was quite impressive! We will definitely be back to try dinner as we had an awesome breakfast today! You had to be there! read more

Food is alway good, along with the service. Great place to grab a casual bite. I enjoy the hometown feel.

The waitress's at Dempseys are the best during the week! Go see Carla and Lisa for breakfast or brunch! Ask for an ooey gooey sticky bun or try their amazing breakfast potatoes! read more

Great traditional diner in a great little town. Everyone was friendly (especially the wait staff) including the locals who I talked to while we ate at the counter. The biscuits were actually buttered and then grilled before serving so they had a crunchy side to them. We will be back soon, even if it is just to get a great cup of coffee and a piece of pie! read more

Dempseys Grille - Country ham with eggs and sausage gravy on the home fries. - Diners Near Me - Middletown, Maryland

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Traveling from College Park, Maryland, to Columbus, Ohio, my wife and I decided to stop in Dempsey's for lunch. The Yelp reviews that we read from the road were generally very good, and always wanting to eat locally, we decided to stop in. When we entered, there were maybe three other people there, and the women behind the bar seemed a little bored. However, within about half an hour or so, the number picked up and business seemed to be going well. I ordered a Reuben sandwich and chips with coffee, and my wife had a Philly cheesesteak. We both thought the sandwiches were excellent. With diners, sometimes you get a gem and sometimes you get a dud. This was a gem, and we would be regulars if we lived there. The people working there were very nice, and the ambiance was much better than the typical brightly lit generic diner that hasn't been upgraded since the 70s. We both commented on the tasteful decor and the homey feel. If you're in the area and want a good sandwich at a relaxed diner, look them up. And if you're a local who hasn't tried the place yet, do so. read more

Although we've not been overly impressed with anything there, they have a local following and are conveniently in town. Food is just okay in our opinion. Prefer Mountaingate diner on. 40 or the Red Byrd in Keedysville much more. read more

I have been a Dempseys customer over a decade. the old owners left some big shoes to fill. the new owners are still learning. they need to get rid of the young employees who don't know how or care about the job they have, experience counts for a lot in the serving industry! I tip great when I receive excellent service! I don't believe the young employees have that quality. I think they finally hired a qualified manager. the food has always been good same with the service and prices. when the inexperienced servers and employees are fixed I think it will be the Dempseys we all know and love! I'll give them some time to work out the ones who shouldn't be there! some people don't belong in the service industry . the ones who do im pretty sure they worked there. I really enjoyed the servers who looked over 23 and had the experience to never mess up an order and cares about the customers sitting down till they leave with smiles on their faces and full bellys! The quality service is what made Dempseys so great along with the food quality and the prices take one of those away and it's just another restaurant! Hopefully they read this and make adjustments! I know I would! I enjoyed eating there after playing golf a mile or two away, my nephew told me about Dempseys. Before I went to main cup and they are really pricey so Dempseys was a refreshing change it's been over a decade now! if you had a bad experience wait two weeks and try again there worth it The new manager will work this place back into the Dempseys quality and professionalism we all know and expect!!! read more

My only complaint really is that the drinks come from cans, would rather a fountain machine. Steak and cheese sub is delicious and huge! Small local diner with a friendly atmosphere. read more

Dempsey's Grille in Middletown,Md is a small restaurant that does a good business. Why ? Because their food is good, as well as prices. Service is excellent, especially when my daughter-in-law Lisa waits on me, or anyone else. She is the best. It is about 9 miles from me but still enjoy going there. It has that old home atmosphere where everyone enjoys each other. read more

Recently changed owners and the entire vibe is off. Workers don't seem happy. New owners actually came to my table to talk bad about the staff and try to advertise his special hot sauce which he described as "mucus texture". I'm a regular and I will not be back. There is now a ton of really young kids that work here. Seems like the new owners want a hang out for their friends with downtown frederick vibes. But clearly have no restaurant experience. read more

Very yummy food great service very local vibes. Very nice sever said he's name was landon he was very kind and was able to help us out a bunch would definitely recommend. Give the kid a raise! read more

Delicious fresh food and friendly service. Love that breakfast is all day on Sunday.

A delightful surprise on Main Street . Great omelets and wonderful service . The avocado toast was b beyond supreme and highly recommended . read more

Dempseys Grille - Western omelet with a a few extra side orders - Diners Near Me - Middletown, Maryland

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I honestly can never figure out when this place is open. I literally live across the street and can honestly never get food here. Call today a solid 20 minutes before they close, and ask him if I could place a pickup order for a sandwich. Was answered with "uhhhhhhhhh, lemmie see... I knw one of our grills is closed.". Seriously? You're open for another 20 minutes, you make sandwiches and eggs. You're only open till 2, why are you shutting your grill down almost half an hour before you close. Not to mention you didn't even ask what I actually wanted, I didn't want anything that even requires a grill. Either way I told her "you know what, don't worry about it thank you." and left it at that. She said "ok" and didn't really seem to give half a care about it. If you're not even sure if you can make a sandwich in 20 minutes, just forget it. If you're really not interested in selling people food and more interested in going home, I will gladly take my business elsewhere. There are lots of new restaurants in Middletown. Just thought I would support the local business. The few times I have it's been okay, really nothing to write home about. Not to worry, I will go to Tapia's.....or Black Hog..... Or Cinco De Mayo...... Or Main Cup. In summary, lazy business that caters to local regulars (I live across the street by the way) and has no interest in growth. Literally go anywhere else in town before you try here. P. S. Finished this review before they closed. Food for thought. read more

Dempsey's is a friendly comfortable place to eat. The staff welcome you like family. The food is great as is the prices. You don't leave there hungry. Of course , Lisa is my favorite waitress, not only because she is my daughter-in-law, but because her bubbly personality makes you glad you stopped in. All of Dempsey's staff are great! read more

This place has grown on me. It's small, quaint and the food is pretty tasty. It's the perfect breakfast, brunch, and lunch spot in Middletown. It's definitely a spot that is well-liked by and caters to locals. The servers definitely have their favorites in terms of regulars (customers) but the reality is that there aren't that many restaurants around here and this is a cute small town grille. read more

One of my favorite diners to eat at. Always such friendly and fast service and quality food. The French toast was good and the orange juice was good but not very "large". The atmosphere, great service, and good food make this a great spot to stop and eat. read more

Dempseys Grille - French toast and a large orange juice. - Diners Near Me - Middletown, Maryland

Breakfast is my favorite meal of the day, every day and this place has everything I love. Good food, service, old school diner feel in a historic location. read more

I feel like their breakfast is their only decent thing. Don't eat the crab cakes. the people are the only great thing there

Found this place on google maps on the way home from ocean city. Cute little diner, hometown feeling. Great food, great staff. read more

Dempseys Grille - Diner - Diners Near Me - Middletown, Maryland

Stopped here for lunch since we were passing through the area. The options they had were very inviting and plentiful! I had the double bacon deluxe cheese burger with fries. The hamburger was perfectly cooked and the vegetables (lettuce, tomato, onion, and pickles) were fresh tasting and very good. They do have a kids menu and a great grilled cheese for the kids! They staff was very friendly and helpful. The service was very good as they did not let outlet glasses get low! Great Job to all of these folks and if we are ever back in the area, we will definitely eat here again! read more

Just moved out to Frederick. I have been looking for a good home style diner cooking, with a relatively fairly priced morning cocktail game. This place hits it all. $6 mimosas, cheap but delicious plates of food, and a pretty dang courteous staff and new owners. I will def be back. read more

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 Yelp! listing so hopefully more folks will stumble across this great joint. read more

Dempseys Grille - Diners Near Me - Middletown, Maryland

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Such a pleasant surprise to find such a fun place to eat when we were driving through town. We were so excited to see so many familiar family items on the menu, and even more excited to hear they were all homemade! Unfortunately, I would have to say the food was not quite as exciting. Good, but just not quite there. If you order the corn fritters, expect them to be covered in powdered sugar (?!?!). If you order a cream soup, expect it to compete with a Dairy Queen blizzard and be so thick/gelatinous you can hold it upside down without losing it. If you order any vegetables, expect them to come from a can. If you are excited for the homemade pies, don't worry... those also come from a can. My friend's BLT looked good, but nothing to write home about. The one redeeming food, was the carrot cake with pineapple cream cheese frosting. Yum! Overall- quaint environment, lacking in the food. Btw- LOVE that they have Snallygaster ice cream! read more

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We recently took an Airbnb in nearby Myersville, and ate breakfast at Dempsey's Grille two mornings in a row. Aside from the wonderful service, their extensive breakfast menu left us stuffed and satisfied. Among the items we sampled were the piping hot hominy; perfectly-cooked steak and eggs; delectable biscuits and gravy; and a fluffy chocolate chip pancake the size of a manhole cover. The bacon was crispy, the home fries were absolutely to die for, and even the coffee was good enough to drain several cups. Service was excellent as well, and very friendly, especially since we came in near the end of the breakfast shift. Everything was first-rate (we wouldn't have come back the second morning otherwise) and Middletown is lucky to have such a gem on Main Street! read more

Absolutely a complete dining experience! Great food, fun atmosphere, very pleasant staff, super service and beer and wine too boot!! Had a very lovely dinner out!!! Thank you everyone at Dempseys Grille!! read more

Fast and friendly service, solid diner fare (lump crab cake sandwich was excellent) great stop on the way from DC to Crystal Grottoes and Harpers Ferry read more

Clean, comfortable, friendly, affordable and good food. What more could you ask for in a local diner? If you liked Dempsey's before their renovation, you'll really love it now. I met a friend here for lunch, a few days after Valentine's, and the decorations were still up. The changes they've made in seating and decor are welcome improvements. They have a nice selection of comfort foods and some dishes with a twist (Beer Cheese Burger), which makes me want to come back to try more. My friend enjoyed the egg salad sandwich with bacon & cheddar, and I went with the classic Turkey Reuben, which was delicious. The coleslaw was fresh, crunchy, finely shredded and a tad sweet, which I like. The iced tea was freshly brewed and perfectly sweetened. Our server was friendly and attentive, and answered all my questions about the menu. They have a broad selection of homemade cakes and pies. We shared the apple spice cake, which was topped with marshmallow icing and drizzled with Carmel. It was moist and decadent. After lunch we chatted with one of the owners who spoke enthusiastically about the new changes. Definitely give Dempsey's a try!! read more

Dempseys Grille - Daily Specials! - Diners Near Me - Middletown, Maryland

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Dempsey's is the textbook down-home diner with a menu full of comfort food, a buzzing service counter, and a staff that's tops in slinging hash to the assembled hungry masses. It's no-frills food, but it comes fast, hot, and tasty. Had a heck of a grilled steak sandwich and cup of hot chicken vegetable soup on the side, with lots of strong hot coffee kept topped up by the efficient and affable counter staff. Within minutes of sitting down, I had a mug of coffee and a menu. A blink later, my order was in and before you know it there's a plate in front of you. And this place was packed. I was in, fed, and out the door with a boxed slice of apple pie to go inside of 25 minutes. Can't ask for much more. read more

New to the country from the city - we love great food and friendly service and Dempsey's give us both! My daughter and I enjoyed a perfectly grilled Rueben and burger. Our next visit was breakfast - chipped beef gravy and eggs - YUM. And the coffee - nice rich dark blend - this Seattleite was totally satisfied. This is one finely run establishment - sit at the bar and enjoy the great service! read more

I really love this place. It is what it is and it's just great. Dempseys is a quaint diner in the historic part of of Middletown, MD, on Main St. The food is good, menu pretty diverse, and prices are OUTSTANDING. There is a swivel seat diner bar in addition to the main seating area which really amplifies the character of the place. Sitting there with a coffee allows me to mentally disconnect from 2018 and takes me back to my childhood sitting in a similar scene with my dad and grandfather, and watching them talk and read the paper (they always gave me the comics section). There are a couple of specific employees who are really friendly, and overall, I recommend eating here for a quick and casual bite. There's hiking and lots of exploring opportunities nearby, and Dempseys is an excellent choice for a before or after hike meal. Enjoy! Tony read more

Unassuming on the outside but don't let that fool you. You won't leave hungry and you will definitely be back. The food and staff are fantastic; great service, great tasting fresh food and great prices. We have had just about every hot sandwich and special on the menu and we have never been disappointed. Turkey dinner night's Fridat night's are our favorites. Bring your family, go early and go hungry! Cheers to the chef for my delicious Reuben and fries last night. Hot and fresh-yummy! read more

This is a great local family restaurant. Super friendly and a town staple. Two must haves--burger deluxe or taco salad.