12 Best Dog Friendly Restaurants Middletown

Volunteer Brewing Company Brewery • $$
116 W Main St, Middletown

“I went here for the first time tonight. It’s very cozy. The beer is good and the staff is awesome 🥰“

4.8 Superb39 Reviews
JAKL Beer Works Brewery • $$
128 Patriot Dr Suites 11 and 12, Middletown

“So refreshing to see a microbrew list full of porter, stout, brown ales, beers that are actually pleasant to drink. Loved the live music, loved the board game area, loved the big backyard with playground features for littles. We will be back!“

4.8 Superb21 Reviews
Crooked Hammock Brewery Pubs • $$
316 Auto Park Dr, Middletown

Customers` Favorites

Pineapple Express Wings
Grilled Cheese Sandwich
That Burger Is My Jam
Pulled Pork Sandwich
Honey Fried Chicken
Humongous Pretzel
Chicken Sandwich
Longboard Nachos
Grilled Meatloaf
Pineapple Wings

“Absolutely favorite place to gather my friends and loved ones. Celebrate every important event at CH. Always great food and service. It’s just my laid back speed. No such thing as a bad drink here. Staff is always friendly“

4.5 Superb258 Reviews
Sully's Irish Pub Irish Pub • $
12 W Main St, Middletown

Customers` Favorites

Drunken Irish Mussels
Chicken Cheese Steak
Jersey Mike Pretzels
Philly Cheese Steak
Holy Reuben Batman
Steamed Shrimp
Hot Crab Dip
Craft Beer
Wings

“I visited Sully's during a work trip. I ordered the "Holy Rueben Batman" and it was probably one of the best rueben sandwiches I've ever had. It had thick cut pieces of corned beef! The meat was tender and well seasoned. I paired it with a Guinness.

The bar is also a historic location and has all sorts of fun decor and things to read throughout the restaurant. This was a fun spot, and I highly recommend it!“

4.5 Superb65 Reviews
Sweet Melissa Bakery Bakery • $$
5407 Peterson Rd, Middletown

Customers` Favorites

Cake Pops -Gingerbread PB and Peppermint Bark
Vanilla Cake with Vanilla Buttercream
Cookies & Cream Cupcake
Organic Cookie Crunch
Dog Cupcake-Pupcake
Coconut Cream Cake
Gingerbread House
Blueberry Muffin
Strawberry Slam
Rainbow Cookie

“I sent Melissa a picture of a baby hamper with an elephant on it for my daughter’s elephant themed baby shower and they knocked it out of the park with an amazing cake and matching cake pops! So beautiful and even more delicious!! The attention to detail was out of this world. The vanilla cake with raspberry jam filling was five beautiful layers. It was almost too pretty to cut but also so pretty on the inside. I can’t say enough about the artistry, communication, and service. Highly recommend this professional custom cake bakery!“

4.3 Superb96 Reviews
Bruster's Real Ice Cream Ice Cream Shop • $
465 W Main St, Middletown

“The strawberry shortcake sundae is to die for“

3.9 Good23 Reviews
Schaefer's Canal House Seafood • $$
208 Bank St, Chesapeake City - 7.55 miles

Customers` Favorites

Schaefer's Crab Cake Sandwich
Seafood Mango Avocado Stack
Strawberry Lemonade Crush
Schaefers Seafood Pasta
Broiled Seafood Combo
Cream of Crab Soup
Sweet Potato Fries
Shrimp and Grits
Stuffed Flounder
Crab Bruschetta

“Enjoyed dining on the patio. Great combo playing that did not blast your ears. Will have to check back next spring to see if they return.“

4.4 Superb252 Reviews
Cantwell's Tavern Gastropubs • $$
109 Main St, Odessa - 3.21 miles

Customers` Favorites

Southern Fried Chicken Sandwich
Filet Medallions with Au Jus
Cantwell's Meat Lovers Pizza
Fried Brussels Sprouts
Chesapeake Flatbread
Chefs Tasting Board
Crab Cake Sandwich
Seared Tuna Nachos
Traditional Wings
Charcuterie Board

“We had our company Christmas party here and the event coordinator Morgan did a phenomenal job. She made it so easy and so simple that all we had to do was show up eat and have a good time. The food was extraordinary and all the kids had a wonderful time along with all the employees.“

4.1 Good146 Reviews
UnWined on the Water American • $$
285 Plum Point Rd, Elkton - 10.75 miles

Customers` Favorites

Blackened Rockfish Tacos
Blackened Shrimp Tacos
Bacon Wrapped Scallops
Irish Fish and Chips
Maryland Crab Soup
Crab Cake Sandwich
Sesame Seared Tuna
Traditional Wings
Chicken Tenders
Carolina Burger

“great service. great food. great boaters“

4.1 Good117 Reviews
Sweet Cowolines Ice Cream Shop • $
1074 Augustine Herman Hwy, Elkton - 9.47 miles

Customers` Favorites

Hand Dipped Ice Cream

“Our company fishing trip was today, and on our way home we were looking for a place to stop for ice cream. We called ahead to be courteous, and they were happy to take our tour bus. We showed up with a DOUBLE DECKER tour bus and Ashlynn and Shannon were amazing. They had us in and out of there as quick as ever for a group our size! They handled things so professionally and politely, and were eager to please all of us. The ice cream and all of the other treats were delicious! There was not one complaint among any of us! We all got a group photo with Cowoline the Cow and everyone was raving about the place on the way home. Thank you, ladies, for making our evening!! It was such a sweet place to stop and we would highly recommend it!! - On behalf of Scenic Ridge Construction... THANK YOU!!“

4.6 Superb35 Reviews
The Bayard House Restaurant Seafood • $$
11 Bohemia Ave, Chesapeake City - 7.41 miles

Customers` Favorites

Crab Bisque with Garden Salad
Oysters on the Half Shell
Stuffed Anaheim Peppers
Jumbo Lump Crab Cake
Maryland Crab Cakes
Mixed Greens Salad
Chicken Parmigiana
Bourbon Pecan Pie
Rockfish Sandwich
Raw Oysters

“My daughter and son-in-law brought us to the Bayard House over the Christmas holidays 2024, and we were impressed-with the food, the service, the atmosphere, and the views! We wanted to do something special for our Army Captain daughter, Noella Rogers, when she promoted to Major yesterday. Remembering how much she and her husband, Jeff, love Bayard House, we called about getting a gift card. Chris Amon, (not sure of the spelling), Assistant General Manager, answered. When he told me that we'd have to come in and purchase it, I told him that we lived in Texas, so that wouldn't be possible. I was about to hang up, but Chris asked where my daughter lives. When I told him, he said that he lived close to her town and volunteered to hand-deliver it! Wow! He didn't have to do that! Not only did he hand-deliver it this morning, April 24th, he bought and placed it inside a card for her. Talk about going above the call of duty! Bayard House, hang onto Chris because that guy is gold! Everyone else, if you haven't tried it out yet, go get you something wonderful to eat at Bayard House! Chris, we look forward to thanking you in person the next time we come to Maryland for a visit!“

3.8 Good105 Reviews
Grain H2O Gastropubs • $$
3006 Summit Harbour Pl, Bear - 6.84 miles

Customers` Favorites

Waldorf Chicken Salad Sandwich
Short Rib Grilled Cheese
Sweet Potato Fries
OMG Crabby Pretzel
Chicken Nachos
Fried Pickles
Lobster Roll
Crab Nachos
Tater Tots
OMG Burger

“Awesome awesome place , I had a great server ,I believe her name was raina. Awesome food .
Back today for crabcakes, great good as usual, great service with the best atmosphere ?
My daughter had a brisket sandwich which wasn't the most traditional brisket we ever had ,but this isn't a bbq place after all.“

3.3 Good131 Reviews

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