12 Coastal Maryland Restaurants With Chesapeake Views (And Even Better Seafood)
The Chesapeake Bay has shaped Maryland’s culture, history, and cuisine for centuries. Today, its waterfront restaurants carry on that legacy, offering both rustic charm and refined elegance.
From weathered crab houses filled with laughter to candlelit dining rooms with panoramic views, these destinations invite you to savor not just seafood, but the very soul of Maryland’s coast.
1. The Narrows Restaurant: Where Tradition Meets Waterfront Elegance
Situated perfectly on Kent Narrows, this Eastern Shore classic has been serving up spectacular seafood for generations. The panoramic water views complement every meal, making even a simple lunch feel special.
Their lump crab cakes are legendary – packed with sweet meat and minimal filler. My grandparents took me here for my 10th birthday, and I still remember the taste of that first perfect crab cake.
Come at sunset for the golden hour glow across the water while you savor their award-winning crab soup.
2. Bridges Restaurant: Dock-and-Dine Paradise
Pull up by boat or car to this airy Kent Narrows gem where the expansive deck offers front-row seats to passing watercraft and stunning sunsets. The casual vibe belies the serious quality of their seafood offerings.
The kitchen excels with seasonal specials that showcase whatever’s freshest from local waters. Their cocktail menu changes with the seasons, but always features creative takes on classics.
Time your visit for happy hour when the bar buzzes with locals sharing stories of the day.
3. Harris Crab House: Authentic Bay-to-Table Experience
Family-owned for decades, Harris delivers the quintessential Maryland crab feast experience. The rooftop bar provides sweeping views of the bay while you crack into steaming buckets of perfectly seasoned blue crabs.
Thursdays bring oyster specials that draw shellfish lovers from miles around. The staff here know their seafood – ask them which creek today’s oysters came from, and they’ll tell you without hesitation.
I once spent a summer afternoon here with friends, hammers in hand, learning the fine art of picking crabs from a 70-year-old waterman at the next table.
4. Libbey’s Coastal Kitchen: Modern Elegance Under the Bay Bridge
The dramatic silhouette of the Bay Bridge frames every meal at this sophisticated Stevensville spot. Floor-to-ceiling windows ensure unobstructed views while you dine in contemporary comfort.
The menu artfully blends Chesapeake traditions with modern culinary techniques. Try their crab-stuffed rockfish for a perfect marriage of local flavors.
Cocktails here are crafted with house-made syrups and local spirits, making the bar program as noteworthy as the food.
Reservations are essential, especially for those coveted window tables at sunset.
5. Cantler’s Riverside Inn: The Watermen’s Gathering Place
Hidden down a winding road outside Annapolis, Cantler’s feels like a delicious secret. This no-frills crab house has served the community since 1974, with many of today’s suppliers being the children and grandchildren of the original watermen who sold here.
The massive outdoor deck puts you right over the water where you can watch boats coming in with the day’s catch. Their steamed crabs arrive at your table hot, heavy, and perfectly seasoned with that signature spice blend.
Back in college, I worked summers here cracking crabs until my hands were raw – the staff still remembers me when I visit with my own kids now.
6. The Point Crab House: Mill Creek’s Hidden Gem
Tucked along Mill Creek in Arnold, The Point offers a laid-back atmosphere where time seems to slow down.
The wooden deck extends right to the water’s edge, providing front-row seats to passing boats and spectacular sunsets.
Their crab dip arrives bubbling hot, loaded with lump meat and served with pretzel bread for dipping. The seafood is consistently fresh, with daily specials reflecting whatever the local boats brought in that morning.
The crushes here – Maryland’s signature cocktail made with fresh-squeezed juice – come in mason jars and pack a delicious punch.
7. Chart House Prime: Annapolis Harbor’s Crown Jewel
Perched at the edge of Spa Creek, Chart House Prime offers some of the most spectacular panoramic views in Annapolis. The tiered dining room ensures every table enjoys the harbor vista through walls of glass.
While primarily known for prime steaks, their seafood tower is a monument to marine delicacies – multi-tiered platters of oysters, clams, lobster, and shrimp. Sunday brunch here has become something of an institution among locals.
I proposed to my wife here years ago, and the staff still remembers us when we return for our anniversary dinner each year, always saving “our table” by the window.
8. STARS at Inn at Perry Cabin: Luxurious Waterfront Dining
Set within the refined grounds of St. Michaels’ most elegant resort, STARS delivers sophisticated dining with unparalleled Chesapeake views. The restaurant’s elegant interior features nautical touches that nod to Maryland’s maritime heritage.
The menu showcases the region’s bounty with artistic presentation and impeccable technique. Seasonal ingredients shine in dishes that honor tradition while embracing innovation.
The wine program here is exceptional, with knowledgeable sommeliers guiding guests through perfect pairings. Reserve well in advance – tables here are among the most coveted on the Eastern Shore.
9. The Crab Claw: St. Michaels’ Historic Harbor Staple
For over 60 years, The Crab Claw has anchored St. Michaels’ harbor, serving generations of families and becoming as much a landmark as the neighboring maritime museum. The open-air decks put you practically in the harbor, with boats passing just feet away.
Their award-winning crab cakes contain so little filler you’ll wonder how they hold together. The steamed crabs arrive hot and heavy, dusted with their secret spice blend that locals swear is the best on the bay.
On summer weekends, you’ll find a mix of boaters, tourists, and locals, all united in the messy, delicious ritual of picking crabs and watching harbor life unfold.
10. Waterman’s Crab House: Rock Hall’s Dockside Treasure
The heart of Rock Hall’s working harbor beats at Waterman’s, where commercial fishing boats dock just steps from your table. This unpretentious spot delivers authentic Eastern Shore flavors with a side of maritime charm.
Their steamed crabs are the main attraction – always heavy, hot, and seasoned to perfection. The rockfish, often caught the same day it’s served, comes prepared simply to let its fresh flavor shine.
Live music on the deck creates the perfect soundtrack for summer evenings. You might even spot the captain who caught your dinner tying up his boat while you dine.
11. Tickler’s Crab Shack: Tilghman Island’s Waterfront Wonder
Part of the charming Wylder Hotel property, Tickler’s brings casual crab feasting to a picturesque Tilghman Island setting. The bayside decks and dock seating put you so close to the water you could practically dangle your feet in.
Maryland blue crabs are the star, steamed to order and piled high on brown paper. Their crab dip, rich with lump meat and Old Bay, has developed a cult following among visitors and locals alike.
Orange crushes – that Maryland specialty of fresh-squeezed orange juice, vodka, triple sec, and sprite – flow freely here, especially during their generous happy hour.
12. Pier 450: Southern Maryland’s Waterfront Revelation
At the southern tip of Maryland’s western shore, Pier 450’s POV Restaurant offers some of the most expansive Chesapeake views you’ll find anywhere.
The modern glass-walled dining room and sprawling lawn seating provide unobstructed panoramas across the bay.
The menu highlights the meeting of Chesapeake and Southern culinary traditions. Oysters harvested from waters visible from your table arrive perfectly shucked and glistening.
Time your visit for sunset when the sky puts on a spectacular show of colors reflecting across the water.
During my last visit, we spotted dolphins playing just offshore while sipping our pre-dinner cocktails.