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Dog Friendly Restaurants in Chestertown, MD

There are 3 dog-friendly restaurants in Chestertown that welcome dogs at their outdoor tables, and 38 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!

Pet Friendly Luisa's Cucina Italiana

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.

Pet Friendly Figg's Ordinary

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.

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.

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!

Pairings Bistro

Pairings Bistro

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

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.

Stevensville Crab Shack

Stevensville, MD

Stevensville Crab Shack

One-stop shop for all things seafood. Umbrella covered picnic tables are dog friendly.

Waterman's Crab House

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!

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.

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.

Ten Eyck Brewing Company

Ten Eyck Brewing Company

Ten Eyck Brewing Company is a dog-friendly brewery located in Queenstown, MD. Fido is welcome to accompany you at an outdoor table while you sip on a handcrafted beer, cider, or non-alcoholic soda. A small menu features snacks and a charcuterie board with local meats, cheeses and bread. For something more hearty, head to the on-site food truck for a tasty curry or taco.

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.

Kitty Knight

Kitty Knight is a full service restaurant in Georgetown, MD serving a farm-to-table menu on a dog-friendly outdoor patio.

Big Bats Cafe

Bring Fido to the Big Bats Cafe, a dog-friendly sports bar in Stevenson, 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.

Bushmill Tavern

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.

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!

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.

Love Point Deli Wine & Spirits

Stevensville, MD

Love Point Deli Wine & Spirits

Love Point Deli Wine and Spirits is a classic deli that provides handhelds with fresh meat and cheeses. They have a dog-friendly picnic table outside so you can bring Fido. The deli menu includes a variety of fresh subs, sandwiches, and wraps with several vegetarian options. The store also provides a broad selection of wine and beverages to take home with you. The deli is open Monday through Saturday from 9am to 5pm and Sunday from 10am to 4pm.

Lemon N Ginger Asian Grille and Sushi

Lemon N Ginger Asian Grille and Sushi

Lemon N Ginger Asian Grille specializes in Chinese and Thai cuisine. There is plenty of room for Fido at their eleven dog-friendly tables. The menu items include sushi, bento boxes, noodles, rice, and dishes made on the grill or the wok. Their bar is stocked with Japanese beer and sake, and they serve several signature martinis and cocktails. Lemon N Ginger Asian Grille is open Monday through Thursday from 11:00am to 10:00pm, Friday through Saturday from 11:00am to 11:00pm, and Sunday from 12:00pm to 9:30pm.

Rita's Italian Ice

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.

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Chestertown, MD, US