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10 Most Scenic Road Trips to Take on the Chesapeake Bay

by Staff

The Chesapeake Bay, which lies in the US Mid-Atlantic region, is the largest estuary on the North American continent. The Bay’s location was determined after a bolide struck the Delmarva Peninsula around 35 million years ago, leaving a 55-mile-wide crater behind. The impact changed the course of the existing rivers here and created the Chesapeake Bay. This captivating region is renowned for its natural beauty, breathtaking landscapes, and picturesque coastal towns. Embarking on a road trip in the Bay provides an unforgettable opportunity to immerse yourself in the best of what nature offers in the US. You’ll find incredible vistas from every vantage point, historic sites, and mouthwatering seafood dishes here.

Chesapeake Bay Bridge-Tunnel

Traffic on Chesapeake Bay Bridge Tunnel in the summer. Editorial credit: Khairil Azhar Junos /

The Chesapeake Bay Bridge Tunnel (CBBT) is an engineering marvel, but it’s not the best place to start exploring the Bay if you’re afraid of heights and/or suffer from thalassophobia. The CBBT consists of 12 miles of bridges and two one-mile-long tunnels. It stretches past the mouth of the Chesapeake Bay between Delmarva and Hampton Roads in Virginia.

If you have no problem driving around 186ft above the ocean and never wonder what may be lurking far below, you will thoroughly enjoy the unique drive across the Bay’s expansive waters. The journey encompasses magnificent sea views, man-made islands, and passing ships. Several overlooks along the way make it easy to stop and enjoy the wonderful coastal ambiance. And, if it looks like the bridge disappears below the water, it’s because it does. The underwater tunnel and the bridge offer a direct route that saves drivers nearly 100 miles per trip.

Eastern Neck Island

Boating in the Eastern Neck Island. Editorial credit: grandbrothers /

Sitting on Maryland’s Eastern Shore, Eastern Neck Island offers a serene escape from busy city life. Take the scenic route along Wildlife Drive, which loops for seven miles through sparkling marshlands and deep-green forests. As you take in the sights and sounds of nature, keep an eye out for herons, bald eagles, tundra swans, and hawks.

The Eastern Neck National Wildlife Refuge forms part of the Chesapeake Marshlands National Wildlife Refuge Complex, which is one of over 565 in the US. The island offers just under 2,300 acres of unspoiled nature between the Chesapeake Bay and the Chester River. The wildlife is the main drawing card, but a road trip to Eastern Neck Island will also unveil its rich history, starting with pre-Columbian Native American remnants.

Michaels To Tilghman Island

hesapeake Bay at sunset, in Tilghman Island, Maryland.
Chesapeake Bay at sunset, in Tilghman Island, Maryland.

If you want to combine a road trip with learning about the Chesapeake Bay, Tilghman Island is probably the best place to start. Set off from the historic town of St.Michaels with the nose of your vehicle pointing towards the island. Along the way, you’ll encounter some of the most charming fishing villages in America, beautiful waterfronts, and bright green farmlands. St. Michaels offers a glimpse back in time to the Colonial era with its distinctive architecture, while the Chesapeake Bay Maritime Museum has everything from wedding venues to exhibitions to explore.

Finally, when you’re hungry from driving, you can indulge in fresh seafood in one of Tilghman Island’s famous waterfront restaurants. While at Tilghman, you can visit the several creeks and rivers or go kayaking and paddleboarding before retiring for the day in one of the stunning guesthouses or hotels.

Annapolis To Kent Island

The scenic Kent Island, Maryland.
The scenic Kent Island, Maryland.

For another road trip adventure involving the Chesapeake Bay Bridge, you can start from Annapolis, Maryland, cross the bridge and drive toward Kent Island. This awesome road trip treats you to never-ending water views, rolling hills, and idyllic countryside. While still in Annapolis, you can take to the cobblestone streets to visit the US Naval Academy. After you’ve gaped at the views from the bridge, you can enjoy waterfront parks, marinas, and the Chesapeake Bay Environmental Center on Kent Island. Kent Island is the largest island in the Bay and offers two beach parks, Matapeake State Park and the Cross Island Trail, which is perfect for bicyclists.

Harriet Tubman Underground Railroad Byway

A replica of the Maryland Steamboat Company”s building on the Choptank River and is a stop along the Harriet Tubman Underground Railroad Byway.

If you want to traverse Maryland’s Eastern Shore and also explore Delaware and Philadelphia, the Harriet Tubman Underground Railroad Byway is the only way to go. This scenic route honors the heroic efforts of Harriet Tubman on the underground railroad and takes you through unmatched landscapes and past historic sites. On this route, you will also pass the Blackwater National Wildlife Refuge, where migratory birds cause a colorful spectacle. There is also the Harriet Tubman Underground Railroad Visitor Center that you can visit before taking the byway.

Chincoteague Island

Wild horses of Assateague Island National Seashore
Wild horses of Assateague Island National Seashore.

If you’re inclined to head south for your next road trip, venture to Chincoteague Island, which is famous for its natural beauty and wild ponies. Beach Road takes you along a path that offers panoramic views of wild marshes, dramatic dunes, and the restless Atlantic Ocean. On this road trip, you can stop to visit the Chincoteague National Wildlife Refuge and the Assateague Island National Seashore, which is home to an array of wildlife and gorgeous beaches.

Smith Island

Woman fishing i
A woman fishing in the waters along the Smith Island.

If you want to get up close to the ocean on your upcoming road trip, why not take a ferry from Crisfield, Maryland, to reach Smith Island? Once you step foot on the beach here, the tranquil atmosphere will envelop you as you learn more about the remote island community and its crabbing traditions. Smith Island is also known for crab shanties and breathtaking waterways. The Smith Island Culture Center provides anecdotes and historical tales about the island, and there are several nature trails to hike if you want to get a little exercise while on your trip. When you get hungry, you can end a delicious seafood meal with the island’s dessert specialty, Smith Island cake.

Solomons Island Loop

Drum Point Light, Chesapeake Bay
Drum Point Light on the Chesapeake Bay.

The Solomons Island Loop offers yet another way to take a trip around the Chesapeake Bay. Situated at the confluence of the Bay and the Patuxent River, this road trip offers water views and the opportunity to visit the Drum Point Lighthouse. A thread of maritime history runs through the island, and you can learn more about it by visiting the Calvert Marine Museum. On the island, you can visit the charming Solon’s Boardwalk, where you’ll find restaurants, shops, and marinas.

Oxford To Cambridge

Aerial view of Oxford, Maryland on the Chesapeake Bay
Aerial view of Oxford, Maryland, on the Chesapeake Bay.

One of the best road trips in the Chesapeake Bay area is the beautiful Oxford to Cambridge corridor located on Maryland’s Eastern Shore. Start in Oxford, which is one of America’s oldest towns known for its extensive maritime history. Here you can explore the waterfront, visit the Oxford-Bellevue Ferry and enjoy magnificent views of the Tred Avon River. As your journey takes you onward to Cambridge, you’ll find a town rich with African American heritage, detailed by the Harriet Tubman Museum and Educational Center. Extend your road trip by visiting the historic downtown area and dining at the excellent local seafood eateries.

Tangier Island

Houses on the marshes of Tangier Island, Virginia, in the Chesapeake Bay.
Houses on the marshes of Tangier Island, Virginia, in the Chesapeake Bay.

For another island road trip, take a ferry from Crisfield or Reedville, Virginia, to reach Tangier Island, an isolated community in the Chesapeake Bay. Tangier Island is known for its distinct dialect, traditional fishing practices, and unique landscapes. Here, driving along the narrow island roads will take you past old but charming homes, marshes, and waterways. While on the island, you can take a boat tour to learn more about its history, go crabbing or fishing, and dine at local seafood restaurants.

Taking a road trip through the Chesapeake Bay region promises a journey filled with history, charm, and beauty. Just remember to respect the environment during whichever route your choose to take and follow local regulations as you savor the sights and sounds of this remarkable region. 

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