7 Most Scenic Drives in Chesapeake Bay

Rolling hills, winding bridges, and salty air—oh my! You’ll find all of these in Chesapeake Bay, making it the perfect place for a road trip to remember. From Maryland’s scenic byways to Virginia’s island ferries, every mile promises something different. Whether you’re simply passing through or planning a weekend stay, you’ll find beautiful coastal towns, breathtaking overlooks, and enough seafood shacks to keep your taste buds happy the whole way around the Bay. These seven scenic drives capture the very best of it.

Annapolis to Kent Island via Chesapeake Country Scenic Byway, Maryland

If you want a drive that feels like the Bay in one long, beautiful stretch, start with the Chesapeake Country Scenic Byway. This all-American road winds along Maryland’s western shore, connecting historic towns and sparkling water views at every turn. Cross the Chesapeake Bay Bridge for panoramas, then stop in Annapolis to explore the United States Naval Academy. Sandy Point State Park is another must-see. Here, where sailboats line the horizon, fishing is a favorite pastime, and the Sandy Point Shoal Lighthouse welcomes visitors from everywhere. End your day with crab cakes on Kent Island, which certainly taste better paired with a waterfront sunset. It’s a drive that is equal parts historical and scenic.

Crisfield to Tangier Island via Tangier Island Ferry Drive, Virginia

For a route that trades traffic for tide, take the Tangier Island Ferry. Start in Crisfield, Maryland, and board the ferry to Tangier Island, a small Virginia community tucked right in the middle of the Bay. This isn’t just a drive, it’s a step back in time. Wander through the narrow lanes where locals tell stories of the town’s rich history, explore the Tangier History Museum, and grab a bite of freshly caught crab at Four Brothers Crab House & Ice Cream Deck. Then, head to James Parks Marina to watch watermen unload their daily haul before going back to the mainland. Every moment here feels like a glimpse of Chesapeake life before modern times.

St. Mary’s City to Solomons Island via Southern Maryland Blue Crab Scenic Byway, Maryland

Seafood lovers, rejoice! This drive was made for you. The Southern Maryland Blue Crab Scenic Byway winds through St. Mary’s County, where the Bay’s best flavors and views go hand in hand. Start at Historic St. Mary’s City, Maryland’s first capital, to explore its colonial village and waterfront trails. Continue south to Point Lookout State Park, where the Potomac River meets the Bay in a scene made for picnics and photos. End your drive on the Solomons Island Boardwalk, where waterfront restaurants serve steaming crab cakes and fresh-caught oysters as the sun sets below the shoreline.

Montross to Colonial Beach via Virginia’s Northern Neck Heritage Trail, Virginia

History and countryside charm meet on Virginia’s Northern Neck Heritage Trail, a drive that feels both charming and soulful. Begin in Montross, a small town lined with murals celebrating the region’s colonial past, and stop by Art of Coffee for a local pick-me-up before hitting the road. Continue east to Stratford Hall, the birthplace of Robert E. Lee, where mature trees frame the views of the Potomac River. From there, visit the George Washington Birthplace National Monument, where the nation’s first president spent his early years. End your trip in Colonial Beach, unwinding with a glass of award-winning wine at Ingleside Vineyards, one of Virginia’s oldest wineries. With each stop, this drive blends history, hospitality, and seaside beauty.

Salisbury, Maryland to Cape Charles, Virginia via US Route 13 (Eastern Shore Highway)

For wide-open skies and never-ending water views, head south on US Route 13, also known as the Eastern Shore Highway. Start in Salisbury, Maryland, and make your way through a string of laidback coastal towns where the Bay meets the Atlantic Ocean. Stop at the Chincoteague National Wildlife Refuge and see the wild ponies roaming the salt marshes, then relax on the beach at Kiptopeke State Park. Once you reach Cape Charles, grab a sweet treat at Brown Dog Ice Cream and watch the boats come and go from the town’s scenic harbor. This route feels like a summer postcard brought to life; one that's best enjoyed with the windows down and the sea breeze coming through.

Oxford to St. Michaels via Oxford-Bellevue Ferry Loop, Maryland

Looking for a road trip with a side of coastal elegance? You won't be disappointed taking this Oxford-Bellevue Ferry loop. Start in Oxford, one of Maryland’s oldest port towns, where tree-lined streets lead to the Oxford Museum and a handful of waterfront dining spots. Drive aboard the Oxford-Bellevue Ferry, the oldest privately operated ferry in the country, and ride across the Tred Avon River to Bellevue. From there, follow the short, scenic route into St. Michaels, home to the Chesapeake Bay Maritime Museum and its iconic 1879-built Hooper Strait Lighthouse. When you’re there, enjoy more water views, boutique shops, and end your loop with a sunset that makes this Chesapeake trip one to remember.

​​Urbanna to Deltaville via Route 33, Virginia

If you love boats, you're in for a treat! The drive from Urbanna to Deltaville along Route 33 is a short but scenic cruise through Virginia’s boating capital. Start in Urbanna, famous for its annual Oyster Festival, and walk past marinas to see all kinds of boats lined up against the dock. Follow the road south toward Deltaville, a town nicknamed “the boating capital of the Chesapeake Bay.” When you’re here, head to the Deltaville Maritime Museum to learn about wooden boatbuilding traditions and the story behind the Chesapeake Bay meteorite that took place over 35 million years ago. Then grab a bite at The Galley, a cozy waterfront spot known for its fresh seafood platters and friendly, small-town feel.

Next, head to Regatta Point Marina and rent a kayak for a peaceful paddle along the creek. If you’d rather stay on land, stop by Fishing Bay Yachting Club to watch the boats race across the open water. Cap it all off with a sunset on the deck and a book in hand. Now that’s Chesapeake living at its finest!

Experience The Best Drives Through Chesapeake Bay

From drive-on ferries and byways to bridges that skim the water, these scenic drives in Chesapeake Bay show off the region’s best views at every turn. You’ll cross bridges, chase sunsets, and maybe even eat your weight in crab cakes. Whether you came for the history, the seafood, or the salty air breeze rolling through the car windows, each mile reminds you that the Bay is made for slow drives and happy detours.