Dempsey's Grille

Dempsey's Grille Give your taste buds a treat with delicious food from our full-service restaurant and catering company located in historic Middletown, Maryland.

American comfort food made fresh in-house to the extent possible 🍽️
Dine-in · Takeout · Delivery via Uber Eats & YourMenu drivers
Proudly serving Middletown, MD Dempsey's Grille is located on downtown Main Street at a location that has hosted a restaurant for more than 70 years. Our current owners have carried on the tradition for more than five of those years with a diner that is renowned for its fabulous catering services and scrumptious home-cooked food.

🍽️ WEDNESDAY IS CLASSIC DINNER NIGHT!Craving a good old-fashioned dinner? We’ve got the classics — hearty, comforting, a...
08/12/2026

🍽️ WEDNESDAY IS CLASSIC DINNER NIGHT!

Craving a good old-fashioned dinner? We’ve got the classics — hearty, comforting, and just what you need in the middle of the week.

Tonight’s Classic Comfort favorites:

🥩 Homemade Meatloaf — topped with rich brown gravy
🧅 Beef Liver & Onions — tender beef liver with sautéed onions and brown gravy
🍖 Bone-In Pork Chops — grilled and topped with brown gravy

And every dinner entrée is served with your choice of TWO sides!

No trends. No fancy stuff. Just the kind of classic comfort food that feels like dinner should. ❤️

Which one are you choosing tonight — Meatloaf, Liver & Onions, or Pork Chops? 👇

📍 Dempsey’s Grill
⏰ Stop in for Classic Dinner Night

👧🍔 KIDS EAT FREE EVERY TUESDAY! 👦🥞Make Tuesday a family night at Dempsey’s Grill! ❤️Every Tuesday after 3 PM, kids eat F...
08/11/2026

👧🍔 KIDS EAT FREE EVERY TUESDAY! 👦🥞

Make Tuesday a family night at Dempsey’s Grill! ❤️

Every Tuesday after 3 PM, kids eat FREE with the purchase of an adult entrée! 🎉

No cooking, no dishes — just bring the family, relax, and enjoy a delicious meal together. 😊

📅 Every Tuesday
⏰ After 3 PM
🍽️ One free kids meal with the purchase of an adult entrée

Bring the kiddos and join us tonight! ❤️

🍽️ WHAT’S HAPPENING THIS WEEK AT DEMPSEY’S?A new week = another reason to stop by! ❤️ Here’s what we’ve got going on:🥞 M...
08/10/2026

🍽️ WHAT’S HAPPENING THIS WEEK AT DEMPSEY’S?

A new week = another reason to stop by! ❤️ Here’s what we’ve got going on:

🥞 MONDAY — Breakfast & Lunch
Start your week with us! Don’t miss our Hotcake Special — choose 1, 2, or 3 hotcakes with your choice of Strawberry, Blueberry, or Peach-Orange Compote.
⏰ Open until 2 PM.

👨‍👩‍👧 TUESDAY — Kids Eat FREE after 3 PM!
Bring the family for dinner — kids eat FREE with the purchase of an adult entrée. 🎉

🍽️ WEDNESDAY — Classic Dinner Night
Midweek calls for some good old-fashioned comfort food. ❤️
Our Meatloaf Dinner is back!

🍄 THURSDAY — Comfort Food Day
Come hungry for our Pork Schnitzel — hand-breaded in our kitchen and served with creamy mashed potatoes, vegetable of the week & mushroom gravy. 🤤

✨ FRIDAY — Treat Yourself Friday
You made it through the week — now treat yourself!
Come see what’s fresh from our kitchen and save room for something sweet. 😉

👨‍👩‍👧‍👦 SATURDAY — Family Dinner
Gather the family, bring some friends, or split a plate with someone you love. ❤️
And yes — our Pork Schnitzel is available for dinner!

☀️ SUNDAY — Breakfast & Lunch
Slow Sunday mornings are better with breakfast at Dempsey’s. ☕🥞
⏰ Open until 2 PM.

📍 Dempsey’s Grill

👇 Now tell us: which day are we seeing you this week?

🥞 Breakfast just got a little sweeter at Dempsey’s!Our new Hotcake Special is here! Fluffy hotcakes served with butter, ...
08/09/2026

🥞 Breakfast just got a little sweeter at Dempsey’s!

Our new Hotcake Special is here! Fluffy hotcakes served with butter, powdered sugar, and your choice of fruit compote:

🍓 Strawberry
🫐 Blueberry
🍑🍊 Peach & Orange

Choose your stack — 1, 2, or 3 hotcakes — and make breakfast exactly how you like it.

The hardest part? Picking your compote. 😋

Which one are you choosing: Strawberry, Blueberry, or Peach & Orange? Tell us in the comments! 👇

📍 Dempsey’s Grille
Come hungry — we’ll take care of breakfast. 🥞☕️

🍔 Saturday is Family Dinner Night at Dempsey’s! ❤️Some meals are just better when they’re shared! 🍗🍟Grab the family, ord...
08/08/2026

🍔 Saturday is Family Dinner Night at Dempsey’s! ❤️

Some meals are just better when they’re shared! 🍗🍟

Grab the family, order a few favorites, put them in the middle of the table, and share a plate… or don’t — we won’t judge! 😄

Good food, cold drinks, and time together — that’s what Saturday nights are for.

Come hungry and make it a family night at Dempsey’s Grille! ❤️

📸 And yes… those wings are definitely worth sharing. 😉

Fresh Cinnamon Rolls are calling your name 🤎Soft, warm, loaded with cinnamon, and topped with a generous layer of creamy...
08/08/2026

Fresh Cinnamon Rolls are calling your name 🤎

Soft, warm, loaded with cinnamon, and topped with a generous layer of creamy frosting. Exactly the kind of treat Saturday was made for. 😍

Come grab one at Dempsey’s Grille — perfect with a hot cup of coffee. ☕️

But don’t wait too long… they tend to disappear fast!

08/07/2026

🦞 Friday Treat Yourself! 🦞

Our famous Lobster Quiche is back starting this Friday!

Made with rich, creamy filling and generous chunks of lobster in a flaky, golden crust, it’s become one of our guests’ all-time favorites—and for good reason.

✨ Treat yourself this Friday and enjoy a slice before it’s gone. It never stays around for long!

📍Dempsey’s Grill
Come hungry—we’ll save you a slice while it lasts!

🥘 Comfort food done right.Our Hand-Breaded Pork Schnitzel is made from scratch, hand-breaded to order, and cooked until ...
08/06/2026

🥘 Comfort food done right.

Our Hand-Breaded Pork Schnitzel is made from scratch, hand-breaded to order, and cooked until perfectly golden and crispy.

It’s topped with a rich homemade mushroom gravy and served with creamy mashed potatoes and our Vegetable of the Week—the kind of meal that feels like home.

If you’re craving a hearty, comforting dinner, this is one you won’t want to miss.

📍 Available for dinner at Dempsey’s Grille. Come hungry!

🍽️ Classic Dinner Night is Here! 🇺🇸There’s nothing like a homemade Meatloaf dinner to make the middle of the week feel s...
08/05/2026

🍽️ Classic Dinner Night is Here! 🇺🇸

There’s nothing like a homemade Meatloaf dinner to make the middle of the week feel special.

Join us today for our Wednesday Classic Dinner and enjoy our hearty homemade meatloaf served with creamy mashed potatoes, rich brown gravy, and fresh seasonal vegetables.

Comforting, filling, and made with care—just like a home-cooked meal.

📍 Dine in with us today and enjoy one of our favorite weekly traditions at Dempsey’s Grill

🥧 Quiche of the Week Update! 🦞Our Denver Quiche is still available and ready to enjoy!The Lobster Quiche has sold out, a...
08/05/2026

🥧 Quiche of the Week Update! 🦞

Our Denver Quiche is still available and ready to enjoy!

The Lobster Quiche has sold out, and we’re already preparing a brand-new Lobster Quiche with our fresh homemade recipe. It will be coming out of the oven soon!

If you missed it the first time, don’t worry—you’ll have another chance to enjoy this customer favorite. Stay tuned for the announcement when it’s ready! ❤️

Address

Middletown, MD

Opening Hours

Monday 7am - 2pm
Tuesday 7am - 8pm
Wednesday 7am - 8pm
Thursday 7am - 8pm
Friday 7am - 8pm
Saturday 7am - 8pm
Sunday 7am - 2pm

Telephone

+13013717400

Website

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