Dempseys Grille

Middletown, MD · American restaurant

Rating
4.5/5
★★★★★ 4.5
Reviews
20
Rank in Middletown
#11
of 24 restaurants
City Percentile
44%
rating percentile
Address
Dempseys Grille, 116 W Main St, Middletown, MD 21769
Phone
(301) 371-7400
Website
dempseysgrille.com
Status
Opens soon · 7 AM

Dempseys Grille is a restaurant located in Middletown, MD. It is one of 24 restaurants listed in Middletown. Its 4.5-star rating matches the Middletown city average of 4.5 stars. It ranks #11 of 24 restaurants in Middletown. There are 10 photos associated with this location.

About Dempseys Grille

Newly renovated landmark diner located along the National Road in Historic Middletown Valley. 60 miles from Washington and Baltimore. Serving an updated diner menu with healthy options.

Hours

Saturday7 AM–8 PM

Customer Reviews

★★★★★ 5.0 Maria Z · Aug 2025

Found this place via google and I’m glad I selected this for breakfast. Friendly staff. The owner comes around to ask about you multiple times and that really makes you feel at home Although they were a bit late with our order but it turned out great. I would highly recommend this for your classic American breakfast. It’s a nice cosy diner with lots on the menu. Portion sizes are average two people can easily share a breakfast but it’s up to you. It’s a little on the expensive side but I guess that is justified looking at the quality of the food. Coffee was perfect. The best sip of coffee I had in a long long time! Thanks Joel and co. If we’re ever back in the area we will definitely visit again.

★★★★★ 5.0 KyleOfTheBeard · Aug 2025

Dempsey’s Grille is a fantastic little bar and diner located in downtown Middletown, MD. It’s easy to spot from the street and the inside is covered in memorabilia and artwork from past decades. They even have a historical pamphlet that tells the story of how Dempsey’s got started back in the 1800s. I walked in and was sat at the bar by Alex, who was genuinely great to talk to as he took my order. It’s an open kitchen so you can see the chefs cooking everything in the back—something I always appreciate. My order was a patty melt with no tomatoes, buffalo wings, and a Diet Coke. Everything came out hot and fast, and Alex made sure I had what I needed before I dug in. The food was great and exactly to order! No complaints from me and, honestly, the fries were amazing. I love little spots

★★★★★ 5.0 Rebecca Charlene Turman · Mar 2026

They had a wonderful breakfast menu! I ordered eggs, home fried potatoes with peppers and onions, and bacon. The eggs overmedium cooked perfect. The potatoes were cooked with chopped peppers and onions were delicious. Rye toast perfectly buttered. The bacon was crispy. 13 bucks for a very filling breakfast.

★★★★★ 5.0 Kevin Kline · May 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.

★★★★★ 5.0 Dennis Fidotta · Feb 2026

Great Diner-like establishment with delicious food and excellent service. This was our first visit. The food was made from fresh ingredients, including delicious desserts. French fries were made fresh from real potatoes. We will definitely return! Definitely worth it!

Accessibility & Amenities

✓ Wheelchair Accessible Entrance ✓ Wheelchair Accessible Parking Lot ✓ Wheelchair Accessible Restroom ✓ Wheelchair Accessible Seating

Services

American restaurantBreakfast restaurantBrunch restaurantDinerSandwich shop

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This listing is informational. Contact the business directly to verify credentials, services, and availability.