Dog Friendly Restaurants in Chestertown, MD

There are 3 dog-friendly restaurants in Chestertown that welcome dogs at their outdoor tables, and 43 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 Chestertown. Bone appetit!

Luisa's Cucina Italiana

Chestertown, MD

Luisa's Cucina Italiana Dog-friendly Luisa's Cucina Italiana utilizes locally sourced dairy and produce in its traditional Italian offerings. They have a large menu chock full of pasta dishes like Shrimp Fra Diavolo and Spaghetti Puttanesca, plus wood-fired pizzas. Gluten-free and vegetarian options are also available. Reservations are recommended. Please note outdoor seating is only available for your four-legged friend during the warmer months. See Details

Figg's Ordinary

Chestertown, MD

Figg's Ordinary Figg's Ordinary is a dog-friendly cafe in Chestertown, MD. Your pup is welcome to join you at a table along their sidewalk patio. Enjoy their baked goods, breakfast and lunch made with local ingredients. Gluten-free options are available. See Details

Play it Again Sam

Chestertown, MD

Play it Again Sam Play it Again Sam is a pet-friendly restaurant in Chestertown, MD. They offer a few outdoor tables for you and your furry friend. Their menu features espresso, frozen drinks, sandwiches and fresh salads to enjoy. Please note table service isn't available, so Fido must remain outside while you order. See Details

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. See Details

The Jetty Dock Bar

Grasonville, MD

The Jetty Dock Bar The Jetty Dock Bar is an award-winning, dog-friendly restaurant in Grasonville, MD. Fido can join you at an outdoor table and there's even a dog menu! Dog owners can enjoy burgers, sandwiches, wraps and a variety of seafood options. See Details

Pairings Bistro

Bel Air, MD

Pairings Bistro Excellent cuisine and wine selection with outdoor seating friendly for well behaved pooches on leash. See Details

Stevensville Crab Shack

Stevensville, MD

Stevensville Crab Shack Stevensville Crab Shack is a one-stop shop for seafood in Stevensville, MD. The umbrella-covered picnic tables are dog friendly. Please note that Fido must remain outside while you go in to place your order. See Details

Waterman's Crab House

Rock Hall, MD

Waterman's Crab House Waterman's Crab House, located in Rock Hall, MD, is a casual eatery that serves up a variety of fresh, delicious fare with an emphasis on seafood. Fido is welcome to join you at one of their pet-friendly outdoor tables while you enjoy your meal. Start off with an order of the Waterman's Nachos - corn chips topped with crab, shrimp, scallops, creamy cheese sauce, pico de gallo, and green onions. Next, chow down on the Seafood Norfolk Saute - fresh scallops, gulf shrimp, and lump crabmeat sauteed in a white wine and butter sauce, served over penne pasta, with a side house salad. Or go for the Shrimp Po Boy with lightly dusted shrimp, lettuce, tomato, and remoulade served on a French roll! See Details

Cafe Sado

Chester, MD

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. See Details

Red Eye's Dock Bar

Grasonville, MD

Red Eye's Dock Bar Red Eye's offers tacos, steamed clams and shrimp, oyster po'boys, and crab cakes. Dogs are welcome at outdoor tables. See Details

Route 24 Ale House

Bel Air, MD

Route 24 Ale House Route 24 Ale House is a dog-friendly restaurant in Bel Air, MD, where Fido can sit beside you at one of the outdoor tables on the covered patio with heaters and fans. Pair one of their cold beers on tap with classic bar fare like salads, sandwiches, burgers, tacos and chicken. Table service is provided. See Details

Amalfi Coast Italian + Wine Bar

Stevensville, MD

Amalfi Coast Italian + Wine Bar Amalfi Coast Italian + Wine Bar is a dog-friendly restaurant in Stevensville, MD, where Fido can join you at an outdoor table whenever the weather is nice. For lunch, visitors can enjoy paninis, pizza, salads and pasta dishes. Dinner choices also include specialties like veal scallopini, chianti short ribs, scallops with saffron risotto and Tuscan seafood stew. Brunch is served on Sundays. See Details

Libbey's Coastal Kitchen and Cocktails

Stevensville, MD

Libbey's Coastal Kitchen and Cocktails Libbey’s Coastal Kitchen & Cocktails in Stevensville, MD, is a dog-friendly waterfront restaurant with a seasonal, shaded below-deck patio where pups are welcome. Enjoy views of the Chesapeake Bay at this coastal eatery focused on fresh, locally inspired Eastern Shore cuisine and handcrafted cocktails. The lunch and dinner menus include dishes such as fish and chips, duck and scallops, and lobster rolls. See Details

Sugar Doodles Sweet Shop

Chester, MD

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! See Details

The Island at Flying Point Marina

Edgewood, MD

The Island at Flying Point Marina The Island at Flying Point Marina welcomes your leashed pup to join you at an outdoor table on their seasonal sandy patio with waterfront views on the Bush River in Edgewood, MD. They even have a dog menu for Fido to enjoy! Dine on a selection of burgers, sandwiches and pizza along with refreshing cocktails. See Details

Big Bats Cafe

Stevensville, MD

Big Bats Cafe Bring Fido to the Big Bats Cafe, a dog-friendly sports bar in Stevensville, MD. Your pup is welcome to join you on their outdoor patio, and they even have a dog menu! For humans, their menu features breakfast sandwiches, crab dip, pretzel burgers, big fish sandwiches and chicken finger platters. See Details

Bushmill Tavern

Bel Air, MD

Bushmill Tavern Bushmill Tavern is a local watering hole and restaurant with eight dog-friendly tables. Their menu includes wings, sandwiches, burgers, tacos, and paninis. Bushmill Tavern also offers unique starter like their She Crab Fries or Philly Cheese Steak Egg Rolls. Their bar includes martinis, mules, wine, beer, and house cocktails. Bushmill Tavern is open Sunday from 10am to 2am and Monday through Saturday from 11am to 2am. See Details

Java Rock

Rock Hall, MD

Java Rock Java Rock serves up coffee, light bites, and wine in a laid back, cozy atmosphere. There are six tables outside with dog-friendly seating for Fido. Along with classic coffee options, Java Rock offers several house specials like the Mocha Mint Patty and the Night Owl. You'll also find tea, hot chocolate, lattes, and smoothies. They also serve a selection of breakfast bites and lunch plates like paninis, wraps, and soup. From May through November, Java Rock is open Monday through Thursday from 7:00am to 4:00pm, Friday through Saturday from 7:00am to 5:00pm, and Sunday from 7:00am to 3:00pm. From December through April, they are open Monday through Saturday from 7:30am to 4:00pm and Sunday from 7:30am to 3:00pm. See Details

Bark Barbecue Cafe

Stevensville, MD

Bark Barbecue Cafe Bark Barbecue Cafe on Kent Island, Maryland is a dog-friendly restaurant with a menu full of Texas inspired barbecue! There are plenty of outdoor tables for you and Fido. If you're still hungry after trying their savory dishes like brisket and pork belly, top off your meal with their soft serve. See Details

Rita's Italian Ice

Aberdeen, MD

Rita's Italian Ice Rita's Italian Ice on W Bel Air Avenue has pet-friendly outdoor tables and a walk-up window, so you are welcome to bring your dog along. Rita's Italian Ice has dozens of flavors of Italian ices, cream ices, soft serve custard and more. You can choose from flavors like Swedish Fish, Pumpkin Pie, and Green Apple. Get your ice or cream turned into Mistos Shakes, Milkshakes, or Frozen Drinks. Try a Gelati, which is custard on top of an Italian ice, or the Blendini, which blends custard with your choice of toppings. See Details