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Dog Friendly Restaurants in Chester, MD

There are 3 dog-friendly restaurants in Chester that welcome dogs at their outdoor tables, and 161 more nearby. Need help to decide where to eat? Here’s a detailed description of each restaurant, along with pictures and reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Chester. Bone appetit!

Pet Friendly Cafe Sado

Cafe Sado

Cafe Sado is a sleek Asian Fusion restaurant in a big city style atmosphere with dog-friendly outdoor seating. A diverse menu packs plenty of flavor and creativity into delicious dishes like beef wellington, crispy crab wonton, bacon wrapped scallops, pad Thai, green curry chicken, and spicy basil beef. Opens at 11:30am during the week and noon on weekends.

Pet Friendly Sugar Doodles Sweet Shop

Sugar Doodles Sweet Shop

Sugar Doodles Sweet Shop

Grab a sweet treat from Sugar Doodles Sweet Shop, a dog-friendly dessert spot in Chester, MD. They use Vanderwende’s premium ice cream for their scoops, sundaes and signature Extreme Shakes. You and Fido can sit together at the sidewalk tables while you enjoy your treats! Make sure to ask for a pup cup!

Dairy Queen

Dairy Queen is a dog-friendly quick-service food concept serving frozen sweet treats to Chester locals and tourists alike. five outdoor tables are available to dog owners with a sweet tooth wanting to indulge alongside Fido. Dairy Queen's menu is comprised of Grillburgers, artisan-style sandwiches, hot dogs, chicken strip baskets, snacks such as Pretzel Sticks with Zesty Queso, Potato Skins, and chicken snack melts, salads, and sides such as fries, onion rings, and cheese curds. Its menu also includes blizzards, hot desserts a la mode, dipped cones, sundaes, cold and blended coffees, shakes, malts, and Orange Julius drinks. A drive-thru window is also available if you don't want to tie your dog up outside while you go in to order.

Boatyard Bar and Grill

Boatyard Bar and Grill

Seafood lovers will be delighted by the number of appetizing options at Boatyard Bar and Grill in Annapolis, MD. Fido is welcome to join you on the outdoor, dog-friendly patio.

Ava's Pizzeria & Wine Bar

St. Michaels, MD

Ava's Pizzeria & Wine Bar

Wood fired pizza, chicken marsala, and spaghetti and Ma's meatballs are on the menu at Ava's Pizzeria & Wine Bar in St. Michaels, MD. Fido is welcome on the dog-friendly enclosed patio. Stop in for a warm and comfortable dining atmosphere. They even have a doggie menu!

The Jetty Dock Bar

Grasonville, MD

The Jetty Dock Bar

The Jetty Dock Bar is an award-winning, dog-friendly restaurant in Grasonville, MD, where Fido can join you at an outdoor table. The menu includes burgers, sandwiches, wraps, and a variety of seafood options. Be sure to ask for their dog menu!

Federal House Bar & Grill

Federal House Bar & Grill

Federal House is a great pet-friendly spot in Annapolis, MD to enjoy fish tacos, crab-stuffed flounder, and a wide selection of draft beers from across the country. They have dog-friendly outdoor tables with water bowls and even a special dog menu for Fido!

Davis' Pub

Delicious pub fare such nachos, beer battered onion rings, crab cake platters, and grilled chicken sandwiches. Outdoor tables allow dogs.

Foxy's

St. Michaels, MD

Casual, outdoor bar and restaurant that serves seafood, burgers, and a variety of specialty cocktails. Outdoor deck seating is dog friendly.

Stan & Joe's Saloon

Stan & Joe's Saloon

Located in the heart of downtown Annapolis, MD, Stan & Joe's offers an award-winning cosmopolitan menu and dog-friendly outdoor seating. Choose from a variety of tasty options like Buffalo shrimp, chicken quesadillas, jumbo wings, oysters on the half shell, Tex-Mex twin egg rolls, salmon carbonara, and signature fajitas.

Annapolis Smokehouse and Tavern

Annapolis Smokehouse and Tavern

Annapolis Smokehouse and Tavern in Maryland serves up a variety of savory BBQ plates, grilled steaks and chops, hearty sandwiches, and craft beers on tap. Outdoor tables welcome dogs.

Pusser's Caribbean Grille - Annapolis Restaurants

Pusser's Caribbean Grille - Annapolis Restaurants

Pusser’s Caribbean Grille is a casual, waterfront restaurant in downtown Annapolis, MD. The menu includes plenty of seafood options alongside sirloin burgers and an expansive wine selection. Fido is welcome to join you on the waterfront patio.

The Galley

St. Michaels, MD

The Galley, located in St. Michaels, MD, is a casual eatery that specializes in delicious breakfast fare. Fido is welcome to join you at one of their pet-friendly outdoor tables while you enjoy your meal. Try Captain Jim's Breakfast Sandwich - a toasted everything bagel with cream cheese, lox, tomato, red onion, and capers. Or go for the Cali Style Breakfast Burrito with eggs, black beans, cheese, tots, salsa, sour cream, avocado, and your choice of bacon or sausage. The Galley is open Sunday through Friday from 8am to 2pm, and Saturday from 8am to 4pm.

Brian Boru

Severna Park, MD

Brian Boru is an Irish pub that serves traditional dishes and drinks in the surroundings of antique memorabilia from the Emerald Isle. There are six small tables outside with dog-friendly seating under their covered patio. The menu includes classic Irish cuisine like Shepherd's Pie, Lamb Stew, or Corned Beef and Cabbage. Many of their menu items are gluten free, too. They also serve American fare like chicken, burgers, and sandwiches. Happy hour is served Monday through Friday from 2:00pm to 7:00pm with specials on appetizers and house drinks. The bar also serves a list of wine, beer, and Irish beverages. Brian Boru is open Monday through Saturday from 11:00am until late, Sunday from 10:00am until late, and brunch is served Sunday from 10:00am to 1:30pm.

Red Red Wine Bar

Red Red Wine Bar

Red Red Wine Bar has a funky, bohemian theme and hosts a vast array of wine, bourbon, whiskey, and more. Fido can join you at one of their nine dog-friendly tables while you find your new favorite vintage. Not sure which wine you want? Try out one of their specially selected wine flights while you sample from their diverse food menu. Their food selections include flatbreads, seafood, steak, sandwiches, and artisanal cheeses. Brunch is served on Sunday from 10am to 2pm with New Orleans-inspired dishes. Red Red Wine Bar is open Sunday from 10am to 12am, Monday through Wednesday from 11am to 12am, and Thursday through Saturday from 11am to 2am.

Bridges Restaurant

Grasonville, MD

Bridges Restaurant

Bridges Restaurant is a waterfront restaurant in Grasonville, MD overlooking Wells Cove serving fresh seafood and upscale American dishes like filet mignon and specialty pizzas. The restaurant features a large pet-friendly patio and live music on Friday and Saturday nights.

Limoncello Italian Restaurant & Wine Bar

St. Michaels, MD

Limoncello Italian Restaurant & Wine Bar

Limoncello Italian Restaurant & Wine Bar is a dog-friendly restaurant in St. Michaels, MD, where Fido is welcome to join you at an outdoor table. Their menu features fresh seafood, char-grilled flatbread pizzette, handcrafted dishes such as Linguine con Vongole, Branzino con Escarole, and many more signature entrees and pasta dishes. Be sure to save some room for Limoncello’s house-made limoncello tiramisu and a small glass of the namesake lemon liqueur!

Marker 5

Marker 5, located in Tilghman, MD, is a casual waterfront eatery that serves up a myriad of delicious fare. Fido is welcome to join you at one of their pet-friendly outdoor tables while you enjoy your meal. Start off with Fried Calamari lightly-dredged in seasoned flour, flash fried, and served with smoked tomato sauce. Next, chow down on the Smoked Shaved Ribeye Sandwich - a garlic butter-toasted brioche bun topped with house-smoked ribeye steak shaved thin, sauteed onions, peppers, mushrooms, provolone cheese, and horseradish aioli. Or go for the Tuna Tempura served with cucumber salad, sweet soy sauce, avocado mousse, and crispy wonton strips!

Miss Shirley's Cafe

Miss Shirley's Cafe

Miss Shirley's Cafe is a dog-friendly breakfast spot serving breakfast, brunch and lunch in Annapolis, MD. Start your morning off with a coffee and buttermilk pancakes, or stop by for brunch and grab a mimosa and their citrus shrimp avocado toast. Fido can join you at an outside table. Miss Shirley's Cafe also offers a vegan menu.

Founders Tavern and Grille

Glen Burnie, MD

Founders Tavern and Grille

Well behaved dogs welcomed outside.

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Chester, MD, US