Excited Paws & Shore Strolls on The Eastern Shore of Maryland
- Luie Boone
- Jun 17
- 5 min read
This vacation destination is a part of our second series of blog posts titled K9 Kind.
Luie Boone believes every vacation is better with your dog, and he's sniffed out the perfect getaway for you both: Maryland's Eastern Shore. This laid-back region is full of walkable towns, waterfront paths, and plenty of spots where pups are more than welcome.
Start your adventure in St. Michaels, which is a charming harbor town where quiet streets and breezy waterfronts are perfect for strolls with your buddy. In nearby Easton, shady sidewalks and green spaces make it easy to explore paw-in-paw.
Just down the road, Oxford is a doggie dream. It's peaceful, scenic, and even home to a dog-friendly ferry ride. You and your pup can watch the sailboats drift by, before unwinding at a waterfront restaurant that welcomes dogs on their patio.
In Cambridge, enjoy calm river walks and lazy afternoons along the Choptank River. Many of the town’s restaurants feature outdoor seating, where your pup can relax while you enjoy the view. If Luie Boone spots a seagull, it will make his trip!
Chestertown offers historic charm, quiet streets, and friendly faces. Several cafés and taverns also offer dog-friendly outdoor seating!
Next, head to Berlin, which was crowned the “Coolest Small Town in America. It's a colorful, artsy town where pups are practically part of the scene. Browse quirky shops together, then grab a bite at one of the town’s many dog-welcoming patios.
Wind down your day together in Denton and Ridgely, where wide-open spaces and peaceful trails let your dog stretch out and enjoy the fresh air. You’ll also find casual spots with outdoor seating that happily accommodate canine companions.
Wherever you wander on Maryland's Eastern Shore, you'll find that the pace is slower, the people friendlier, and the adventures even better with your pup by your side. From waterfront walks to scenic small towns, it's a place where memories are made one pawprint at a time!
Paws Rest Here
Luie Boone paw-selected this perfect vacation rental for your stay in The Eastern Shore of Maryland. Check it out below!
Rental Name: Chesapeake Pines
This rental has 4 bedrooms with 5 beds and 4 baths.
Photos courtesy of Eastern Shore Vacation Rentals
It features the following amenities:
Waterfront on Broad Creek
Hot tub next to the deck
60-foot dock with water and electricity (Luie Boone wants you to imagine the cannonball he could pull off with that much room for a running start!)
2 pelican pursuit single kayaks, 1 tandem kayak and 1 canoe to explore the lush country lanes and calm waterways
Deck with propane grill
2 hybrid bikes are available for guest use (Luie Boone wonders if you can attach a doggy wagon to the back!)
What does Luie Boone think of this rental? He woofed:
My humans keep talking about this place called "Chesapeake Pines" in the Eastern Shore of Maryland. I’ve been eavesdropping on every word. I’m an expert listener, after all. From what I heard, it’s a pup-friendly cottage by the water. There’s a hot tub and even though I won’t get in, you can bet I’ll be standing guard while my humans soak and relax. They’ve mentioned kayaks, bikes, and a game room, plus a big kitchen where something tasty might accidentally fall on the floor. Hopefully, a tomahawk steak! There’s even a croquet set in the garage and a basketball hoop behind the shed. There will be lots of outdoor fun for my humans, while I supervise them like the good boy I am. In the evenings, we can sit outside, watching the sky change colors over the creek. My humans on the dock and me stretching out beside them, dreaming of squirrels! It sounds like the perfect place for all of us to unwind.
Paws Venture Here
Martinak State Park
This park offers numerous trails, which you can enjoy with your pooch in a landscape that is made up of ancient pine, hardwood forests, tranquil fields, and secluded marshland.
Patriot Cruises
Your buddy is welcome to come aboard with you on the Patriot Cruises and enjoy the scenery on the water. You can even get a picture of Fido steering the ship! Luie Boone would steer the boat to the nearest ice cream shop!
Seth Demonstration Forest
This 121-acre recreational space is a great spot to explore with your canine companion. You can adventure along hiking trails!
Adkins Arboretum
This is a 400-acre garden with miles of scenic paths through woodlands, meadows, and wetlands to enjoy with your pooch.
St. Michaels Nature Trail
This pup friendly 1.3-mile trail skirts the western edge of this scenic town. It goes through woods, across the San Domingo Creek on a wooden bridge, and travels past a horse farm. Luie Boone loves horses!
Muskrat Park
Bring your doggo to this waterfront park, which offers scenic views of the harbor and brick walking paths.
Oxford Town Park
Enjoy leisurely walks with your best friend and take in the scenic views of the Chesapeake Bay. Luie Boone wants to let you know that the park is dog friendly, but, unfortunately, the beach is not.
Ava's Pizzeria & Wine Bar
Visit Ava's Pizzeria & Wine Bine for wood fired pizza, chicken marsala, and spaghetti and Ma's meatballs! Fido is welcome on the dog-friendly, enclosed patio, where they can chow down on a bite from the dog menu! Luie Boone can't wait to try it all.
Luie Boone's Pet Peeve about
The Eastern Shore of Maryland
There's just so much to love about this vacation destination, but there's one thing that's got Luie Boone's leash in a twist. He woofed:
From what I’ve heard about Maryland’s Eastern Shore, it sounds like a total dream. There's bay breezes, seaside strolls, and gull-chasing galore. What’s not to love, right? That’s exactly what I thought… until I heard one word: marshlands. Suddenly, visions of soft sand and salty air were replaced by burrs, stickers, and sharp shells. Uh, excuse me? That doesn’t sound like a vacation; it sounds like a paw trap. Apparently, those picturesque marshes come with a price: prickly terrain. Burrs tangled in my fur? Shells wedged between my toes? Hard pass. But hey, I’m not just any pup—I’m an adventure pup. So I’ll be prepared. Here’s what I’m packing: paw boots for rugged romps, a brush and comb for burr patrol, tweezers for any sneaky stickers, soothing paw balm, and plenty of fresh water. And yes, I’ll stick to the path when I can. There's no shame in playing it smart. I still can’t wait: new coastline, new scents, new stories. Eastern Shore, I’m coming for you... just not bare-pawed!
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