Dempseys Grille

4.5 ( 545 reviews )
Checking... 6:30 AM - 8:00 PM See Hours
$10–20
116 W Main St, Middletown, MD 21769, United States
+1 301-371-7400
Dempseys Grille, located in Middletown, MD, offers a delightful taste of classic American comfort food in a cozy, welcoming atmosphere. As a family-owned establishment, it fosters a strong sense of community and inclusion, making every visit a warm experience. Reviewers rave about their well-crafted menu, which includes everything from delectable breakfast options to savory lunch dishes. The homemade approach is evident, particularly in standout items like bacon, perfectly crispy and full of flavor, and deliciously seasoned home fries. Alicia Jones particularly highlights the desserts, specifically the cheesecakes, noting that the blueberry variant holds a special place in her heart. The diner’s charm is enhanced by the friendly nature of the staff, with many customers commenting on the personal connections formed between the owner and regulars, contributing to a homey feel. Whether you’re indulging in their famous fish sandwich or a hearty corned beef hash, Dempseys Grille is praised for flavor and quality. It's a hidden gem worth revisiting, where each dish feels crafted with care and the comfort of home.

Amenities and More

  • Accessibility
    • Has wheelchair-accessible car park
    • Has wheelchair-accessible entrance
    • Has wheelchair-accessible seating
    • Has wheelchair-accessible toilet
  • Service options
    • Offers takeaway
    • Serves dine-in
    • No delivery
  • Highlights
    • Has fast service
    • Serves great coffee
    • Serves great dessert
  • Popular for
    • Popular for breakfast
    • Popular for lunch
    • Popular for dinner
    • Good for solo dining
  • Offerings
    • Serves alcohol
    • Serves beer
    • Serves coffee
    • Serves comfort food
    • Serves food
    • Serves healthy options
    • Quick bite
    • Serves wine
  • Dining options
    • Serves breakfast
    • Serves brunch
    • Serves lunch
    • Serves dinner
    • Has catering
    • Serves dessert
    • Has seating
  • Amenities
    • Has toilet
  • Atmosphere
    • Casual
    • Cosy
    • Historic
  • Crowd
    • Family friendly
    • Good for groups
    • LGBTQ+ friendly
    • Popular with tourists
  • Planning
    • Doesn't accept reservations
  • Payments
    • Accepts credit cards
    • Accepts debit cards
    • Accepts NFC mobile payments
    • Credit cards
  • Children
    • Good for kids
    • High chairs available
    • Has kids' menu
  • Parking
    • Free of charge street parking
    • Free parking lot
    • Plenty of parking

Reviews For Dempseys Grille

Alicia Jones
May 28,2025
Everything about Dempsey’s exceeds expectations. The menu and ingredients are incredibly thoughtful. Everything down to the seasoning is made in house. The desserts are to die for - special shout out to the cheesecakes. I tried strawberry, original and blueberry - all were fantastic but the blueberry has a special place in my heart. This is an outstanding family owned and ran business that supports diversity and inclusion. They have choices for everyone - comfort food, gluten free options, diabetic options, you name it. I will certainly be back and recommend to all. Good people, good food.
Tara K
Apr 21,2025
We chose Dempseys for our alphabet letter date. The food was good and the fish sandwich was delicious!
R S
Apr 15,2025
Had the corned beef hash. Only thing I would say is make sure you order everything you want. If you want hash browns or home fries you need order them.
Tatiana Burkhead
Mar 29,2025
Small restaurant but when you walk in, you feel welcomed. They were a little busy when we got there. It seems like the owner knows a lot of the customers. The food came out quickly and was very good. It seems like the 3 teens are related (which is cool, but do not fully know). Will be stopping by if we are back in the area!
Bre Harwood
Mar 22,2025
We had a wonderful breakfast at Dempsey’s!! The eggs were flavorful, toast was soft, bacon was crispy, and home fries were seasoned well. It has such a cute little diner atmosphere, too. Highly recommend! :)
Kevin Kline
Mar 14,2025
My wife and I chose Dempsey's as our "D" restaurant for our ABC adventure. This place was probably my favorite so far. The music was literally my Spotify Playlist. Carly the hostess and waitress was a doll. Our food came out hot and we didn't have to wait a long time either. We shared the chili cheese fries and they were bangin'. I had the Dempsey's patty melt and chili topped baked potato. And guess what?! They were both bangin'! I mistook the sour cream as mayonnaise and put half of it on my burger and it was still bangin'. My wife had the cod sandwich and onion rings and she said they were both bangin. It was so chill inside and very comfortable. Chairs were nice and sturdy for my big back self.
Joy Gatewood
Mar 10,2025
Small town charm and world class food. The chicken salad is the bomb. Their cole slaw may be the best I've ever had. I ordered avocado stuffed with chicken salad & a side of Cole slaw - and got a serving size so generous I had to get a to-go box. I plan to return next time I'm in the area and recommend it.
Scott Wheeler
Mar 10,2025
Wonderful local restaurant serving breakfast, lunch and dinner. The breakfasts are outstanding and offer items a la carte or a full breakfast. There is plenty of seating and they also have counter seating. One of the nice things about Dempseys is that it has a delightful, quaint, hometown feel where customers feel welcome, folks talk to you, and there is a relaxed atmosphere. Another nice advantage of this place is that seating seating and dining area are well maintained, modern and very clean. This is a must stop if you're in the middletown area.

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