Dempsey's Grille

Dempsey's Grille From-scratch American comfort food 🍽️
Dine-in · Takeout · Delivery via YourMenu drivers
Proudly serving Middletown

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

Cold beer + Friday night = a pretty good combo 🍻We added some new beer favorites to the cooler at Dempsey’s Grille 👀Now ...
05/15/2026

Cold beer + Friday night = a pretty good combo 🍻

We added some new beer favorites to the cooler at Dempsey’s Grille 👀

Now available:
🍺 Oberon Ale
🍺 Allagash White
🍺 Perpetual IPA

Plus all your classic favorites are still here too.

Perfect with dinner, burgers, crab cakes, wings, or just winding down after a long week ✨

Treat Yourself Friday starts tonight at Dempsey’s Grille.

05/15/2026

Treat Yourself Friday 💛

You asked… so we baked more 🥹
Our homemade cinnamon rolls are back and the smell in the kitchen says it all.

Soft, warm, from scratch, and topped with that perfect icing everyone loves 🤍

Perfect with your Friday coffee ☕️

Stop by for breakfast, lunch, or dinner tonight at Dempsey’s Grille!

"Chicken Pot Pie Night” tonight 🥧🔥Homemade comfort food, flaky crust, creamy filling, and the kind of dinner that feels ...
05/14/2026

"Chicken Pot Pie Night” tonight 🥧🔥

Homemade comfort food, flaky crust, creamy filling, and the kind of dinner that feels like home.

Back again tonight at Dempsey’s Grille — and yes… they’ve been selling FAST lately 👀

Available tonight until sold out.

📍Middletown, MD

Breakfast done right 🍳🦞Our Lobster Omelet is one of those breakfasts you think about all day.Made with lobster, creamy b...
05/13/2026

Breakfast done right 🍳🦞

Our Lobster Omelet is one of those breakfasts you think about all day.
Made with lobster, creamy brie, cream cheese, and topped with feta & fresh green onions — rich, savory, and packed with flavor.

And the best part?
You pick your favorite bread on the side 😊

Perfect for a slow breakfast, brunch date, or simply treating yourself this morning.

Available at Dempsey’s Grille today ❤️

Plan your week with us at Dempsey’s Grille ❤️Tuesday – Kids Eat FREE after 3 PM 👨‍👩‍👧‍👦 One free kids meal with each ad...
05/12/2026

Plan your week with us at Dempsey’s Grille ❤️

Tuesday – Kids Eat FREE after 3 PM 👨‍👩‍👧‍👦
One free kids meal with each adult entrée.

Wednesday – Classic Dinner Night 🍽️
Comfort food favorites, homemade sides, and cozy diner vibes.

Thursday – Chicken Pot Pie Day 🥧
Our homemade chicken pot pie is back — available while it lasts!

Friday – Treat Yourself Night ✨
Good food, desserts, and the perfect excuse to enjoy your Friday dinner out.

Saturday – National Mimosa Day 🥂
Join us for brunch and enjoy our Mimosa Specials all day Saturday!

Sunday – Breakfast & Lunch Only ☀️
We’re open until 2 PM.

📍Dempsey’s Grille – Middletown, MD

After all the Mother’s Day weekend excitement…Monday feels like coffee, comfort food, and a cozy breakfast at Dempsey’s ...
05/11/2026

After all the Mother’s Day weekend excitement…
Monday feels like coffee, comfort food, and a cozy breakfast at Dempsey’s ☕❤️

Thank you for such a busy and beautiful weekend.

🌸 Happy Mother’s Day from all of us at Dempsey’s Grille 🌸Today we celebrate all the amazing moms, grandmothers, stepmoms...
05/10/2026

🌸 Happy Mother’s Day from all of us at Dempsey’s Grille 🌸

Today we celebrate all the amazing moms, grandmothers, stepmoms, and mother figures who make life brighter with their love, strength, and care. 💐

Thank you for everything you do — today is for you. ❤️

We hope your day is filled with good food, family, laughter, and a little time to relax and feel appreciated.

Happy Mother’s Day! 🌷

— Your Dempsey’s Grille Family

Wow… today was BUSY ❤️Thank you to everyone who came out to celebrate Mother’s Day weekend with us at Dempsey’s Grille. ...
05/09/2026

Wow… today was BUSY ❤️
Thank you to everyone who came out to celebrate Mother’s Day weekend with us at Dempsey’s Grille. We truly appreciate every table, every order, every kind word, and every family who chose to spend part of their weekend with us. 🌸

Our team worked hard all day and seeing the dining room full means everything to us.

Mother’s Day specials continue through Sunday — no reservations required 😊

We’re also looking forward to seeing everyone for dinner tonight and again tomorrow for breakfast & lunch! 💐🍳

Come celebrate with us! ❤️

🌸 Mother’s Day Weekend starts Friday at Dempsey’s Grille 🌸Treat Mom to something special this weekend 💕✨ Weekend Feature...
05/08/2026

🌸 Mother’s Day Weekend starts Friday at Dempsey’s Grille 🌸

Treat Mom to something special this weekend 💕

✨ Weekend Features:
🥚 Lobster Omelet
🥪 Chicken Apple Brie Sandwich
🥗 NEW Mango Salmon Bowl

Our new dinner special features grilled salmon, crispy bacon, mango, cucumber, avocado over rice with raspberry vinaigrette ✨

Fresh baked Mother’s Day cupcakes are also coming this weekend 👀🧁

Dine-In • Takeout • Delivery

Classic Dinner Night 🍽️$14 Chicken Pot Pie 🔥Comfort food, homemade, and limited.Today & tomorrow only —when it’s gone, i...
05/06/2026

Classic Dinner Night 🍽️

$14 Chicken Pot Pie 🔥

Comfort food, homemade, and limited.

Today & tomorrow only —
when it’s gone, it’s gone.

05/05/2026

Cinco de Mayo 🌮
One day only — come build your favorites your way

Fresh • Hot • Made to order

📍 Middletown
Dine-in • Takeout • Delivery

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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