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Ratings and reviews

RATINGS
Food
Service
Value
Atmosphere

Details

CUISINES
American, Diner
Meals
Breakfast, Lunch, Dinner
FEATURES
Takeout, Seating, Highchairs Available, Wheelchair Accessible, Table Service
Reviews (46)
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46 results
Traveler rating
23
17
2
1
3
Traveler type
Time of year
LanguageEnglish
Traveler rating
23
17
2
1
3
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Reviewed April 14, 2022

From the moment we entered, everyone was so kind and accommodating. They have gluten free bread and are all very knowledgeable! The food itself was to die for! It was so delicious, I couldn’t stop to take a picture. Such a great find!

Date of visit: April 2022
Helpful?
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed August 29, 2021

Food is just OK. Portions are small and the prices are high. Typical small town diner/breakfast place. Prices are more like New York City than rural Maryland. Omelettes are way overpriced and they don’t come with home fries or breakfast potatoes. I won’t return there.

Date of visit: August 2021
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Reviewed September 1, 2020 via mobile

Middletown has opened a lot of new "up market" restaurants in the last few years... I hope you give Dempseys a chance for simple, good food. Ample parking around back, good service, we get carryout a couple times a month and they always get it...right. I don't know if it's intended or just by happenstance but I started a keto diet this year and they frequently have keto friendly option as specials and on their main menu. When I wasn't keto, their turkey rachel was LIFE. So good. Perfect coleslaw. Yum. Might go back to carbs just for that.More

Date of visit: September 2020
Helpful?1  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed March 16, 2020

This is our favorite breakfast spot in the area. Food is good. There's a new menu, with some new additions to the usual breakfast fare. Service is great, always with a smile, often with some snappy banter. Fun.

Date of visit: March 2020
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Reviewed December 27, 2019

Went there on December 27, 2019 for some pancakes and to show a foreign guest what a small town breakfast joint looks like. I ordered pancakes and after eating one, discovered dry clumps of pancake mix powder throughout the second one. It was gross to...have these clumps in my mouth. I crushed one of the clumps on my plate to show the waitress. She went to the kitchen, came back and said "sorry, I guess we didn't let the batter sit long enough" Upon paying, another waitress asked how everything was and I told her it was terrible. She got owner, who offered to give us the breakfast for free and gave me an excuse like "we try our best but there are always some people..." implying we were "difficult customers". I refused the offer of a free breakfast for both of us and had her deduct the pancakes. My partner felt sick afterwards from the oil his omlette was fried in or margarine on his toast. We wont be going there any more!More

Date of visit: December 2019
Helpful?1  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed November 23, 2019 via mobile

We love Dempsey’s. Classic diner food with great service, nice atmosphere and great food. Their homemade soups and chili are the best!

Date of visit: November 2019
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Reviewed November 10, 2019 via mobile

Stayed in Middletown for 2 nights while on vaca. Decided to go to Dempsey's to get chicken for supper. Order the chicken dinner she said they didn't have any chicken because they were changing their menu. Husband ordered a fish dinner. He wanted the smaller...portion, she gave him the bigger portion. there was four of us for dinner and they were out of a lot of food. Went to pay the bill and told her you charged us wrong he told you the smaller dinner you gave us the bigger dinner. She refused to do anything about it. The entire meal and service (she never refilled drinks, took dirty dishes or offered desert) was not good. We would never recommend this place to anyone. One of the worst meals we have ever had while on vacation!!#More

Date of visit: October 2019
Helpful?1  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed June 22, 2019

Went to Dempsey's while visiting brother...Had a very good Crab cake sandwich,price reasonable.Would deinitely go back again.

Date of visit: June 2019
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Reviewed April 28, 2019 via mobile

Dined here several times. Food and service is always good but the last 3 times we have visited, we have been over charged. They don’t print receipts so I suggest ask for a printed receipt before you pay to verify you are being charged correctly.

Date of visit: April 2019
Helpful?2  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed February 24, 2019 via mobile

We stop in here any chance we get. Food is home made, delicious and very tasty too. Servers are always great. We love that it’s close to home and a very reasonable good meal. There is some parking along Main Street but a municipal lot...not far away, and it’s free. Dempsey’s offers daily specials and are closed on Mondays. Check it out!More

Date of visit: February 2019
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Reviewed January 19, 2019

We enjoy going out to breakfast on the weekends and this is the only place that accommodates early risers in Middletown. The staff has always been very friendly and kind. Breakfast was very yummy! Nice that they has specials. They seem willing to customize anything.

Date of visit: December 2018
Helpful?1  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed January 2, 2019 via mobile

Our party of 8 went there on December 26,2018 for an after Christmas family breakfast. We go there often and have always received great food and service. I'm happy to say that this visit was no different.

Date of visit: December 2018
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Reviewed October 26, 2018

After driving by this place for years we decided to give it a try. We were not disappointed. It is a pretty basic operation with a fairly extensive menu. Additionally, there were a number of specials. Everything we had was good and the service was...friendly. If you are looking for a good basic meal this is the place.More

Date of visit: October 2018
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Reviewed October 7, 2018 via mobile

Website said they were closed but it wasn’t on Sunday! Almost didn’t stop but glad we did. Good food made to order right behind the counter. Service with smile. Will definitely stop again if in the area.

Date of visit: October 2018
Helpful?2  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Reviewed September 23, 2018

Hometown style cooking. Busy, noisy, but breakfast is wonderful. Not expensive. I like the corned beef hash.

Date of visit: September 2018
Helpful?1  
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Frequently Asked Questions about Dempsey's Grille

Yes, Dempsey's Grille offers takeout services.

Dempsey's Grille is rated accordingly in the following categories by Tripadvisor travelers:
  • Food: 4.5
  • Service: 4.5
  • Value: 4.5
  • Atmosphere: 4.5