Delaware’s best road trips follow the Atlantic coastline, historic inland waterways, and the Underground Railroad. Along the Red Clay Scenic Byway, you can trace the watershed across New Castle County and cross one of the longest covered bridges in the state, while the Historic Lewes Byway connects tidal marshes and sand dunes to the World War II Observation Tower at Cape Henlopen State Park. Meanwhile, the Harriet Tubman Underground Railroad Byway offers an essential look at sites used for cover and transport during one of the nation’s most critical moments in history. These eight routes can take half an hour, an afternoon, a weekend, or longer, depending on your mood and preference, but they all leave a lasting impression and highlight the best of Delaware’s history, culture, and natural scenery.

Brandywine Valley National Scenic Byway

The Brandywine Valley National Scenic Byway is a 12.5-mile drive that packs a lot into a short drive. It goes from Wilmington on Routes 52 and 100 to the state line near Chadds Ford, Pennsylvania. Start at Rodney Square in downtown Wilmington, then watch the scenery transform from an urban setting into rolling country hills. Along the way, there are several attractions and sites to explore. You could even delay the start of the drive with a trip to the Delaware Art Museum or the Delaware Museum of Natural History, both in Wilmington.

Once you hit the road, you’ll pass luxurious properties once owned by the du Pont family, like the Nemours Estate in Wilmington, or the Winterthur Museum, Garden & Library, both of which are open to the public. Centerville offers antiquing and Brandywine State Park, while Greenville, another suburban community near Wilmington, is more upscale with lovely homes. A drive straight through will take about 20 minutes, but since many consider it an “arts and gardens” drive, a more leisurely pace is recommended.

Red Clay Scenic Byway

Approximately 27 miles long, the Red Clay Scenic Byway consists of 28 picturesque secondary roads in New Castle County within the Red Clay Creek Watershed. Since it features so many roads, it’s fair to say there is no formal beginning or endpoint; rather, it follows an interconnected network of streams along the natural flow of the valley. It’s located approximately between Routes 48 and 52, and it meanders from the outskirts of Wilmington through pastoral and photo-worthy areas.

Attractions to see include the Mt. Cuba Center’s 650-acre botanical garden, the Ashland Nature Center, and the Marshall Steam Museum, which features the world’s largest operating collection of Stanley Steamer cars. There are also two covered bridges to discover near the byway: the cheery red Ashland Covered Bridge, near the Ashland Nature Center, and the Wooddale Covered Bridge in Wooddale, one of the longest covered bridges in the state. A drive straight through will take about an hour, but allow a few more to thoroughly enjoy.

Nanticoke Heritage Byway

The Nanticoke Heritage Byway mostly follows the Nanticoke River, which is one of the mid-Atlantic’s best-preserved waterways. The drive is around 35 miles and features several historic small towns and scenic views of Sussex County. Many of the towns along the byway have strong shipbuilding roots dating back to the 1700s. The byway starts at Hearn’s Pond, north of Seaford, and ends at Trap State Park near Laurel.

Seaford, often called the “Nylon Capital of the World” because DuPont built its first nylon factory there, is home to the Seaford Museum and the Governor Ross Mansion. Also close by is the Woodland Ferry that takes people and vehicles across the Nanticoke. It’s the oldest operating river ferry in the country. Bethel has the Bethel Heritage Museum and a very inviting Main Street, while Laurel contains a large historic district listed on the National Register of Historic Places. Driving time without stopping takes about an hour, but there are plenty of reasons to stop and explore.

Delaware Bayshore Byway

At about 100 miles long, the Delaware Bayshore Byway borders the Delaware Bay and is ideal for those who want a long, mostly straight, leisurely drive. In fact, its nickname is “the road less traveled.” It wanders past some of the largest preserved coastal marshlands on the East Coast. The marshes are stopovers for hundreds of migratory bird species and are also vital spawning sites for horseshoe crabs. The route passes through numerous historic towns, beginning in New Castle and ending near Lewes, mostly along Delaware Route 9.

In New Castle, there are two historic house museums from early colonial times, the Dutch House and the Amstel House, while Delaware City is a waterfront community and home to Fort Delaware on Pea Patch Island, a Union Civil War fort and prison for Confederate soldiers. Woodland Beach is quiet with a nice pier to stroll on, and the byway also goes by the Bombay Hook National Wildlife Refuge and the Air Mobility Command Museum in Dover. Driving straight through takes a couple of hours, but with plenty of shops and eateries, it’s a trip that invites stopping and smelling the roses—or at least, the bay breezes.

Harriet Tubman Underground Railroad Byway

As the name suggests, the Harriet Tubman Underground Railroad Byway features the route and many stops enslaved people made on their road to freedom. It officially begins in Maryland, but the Delaware section is about 95 miles long, starting in Camden and Dover, then continuing north on US 13. It also passes through Smyrna, Middletown, and Odessa before following the Delaware River to Wilmington, where it connects a number of Underground Railroad sites, including places where people fought against slavery and known hiding spots.

Historical sites include the Star Hill Museum in Camden, the Camden Friends Meeting House, and the Old State House Museum in Dover. Close by is the Golden Fleece Tavern, where delegates met in 1787 to ratify the new US Constitution, marking Delaware as the country’s very first state. Other notable pit stops include the John Dickinson Plantation in Dover and the Blackbird State Forest in Smyrna. Allow three hours to drive straight through, and longer for the fascinating, educational stops along the way.

Historic Lewes Byway

The Historic Lewes Byway offers a blend of coastal scenery and early American history, with views of tidal marshes, waterways, and preserved landscapes alongside sites that reflect Lewes’s colonial and maritime past. The route is actually a string of several roads totaling about 12.5 miles, and the individual segments include New Road, Pilottown Road/Front Street, Savannah Road, Kings Highway, Gills Neck Road, and Cape Henlopen Drive. It begins at the intersection of Route 1 and Nassau Road/Old Orchard Road and ends at the Cape May Lewes Ferry Terminal.

The route runs adjacent to tidal marshes, such as the Great Marsh Preserve area, and also connects to Cape Henlopen State Park, with its dunes, beaches, and watchtowers constructed during World War II to protect the coast. The iconic Delaware Breakwater East End Lighthouse is one of the best in the state to see, and if you time it just right, the sunsets are gorgeous. A continuous drive will take under 30 minutes, but it’s well worth taking the time to wander.

Bethany Beach to Ocean City

Although not an official byway, the approximate 15-mile drive on Route 1 from Bethany Beach to Maryland’s border town of Ocean City is a lot of fun. Along the way, you’ll have water on both sides at times, with sweeping bay views to the west and glimpses of the Atlantic to the east, plus stretches of beach towns, coastal parks, and classic seaside attractions. It’s situated between the Atlantic Ocean and Little Assawoman Bay, Assawoman Bay, and Isle of Wight Bay, in that order from North to South. There are dozens of things to explore on the famous Bethany Beach Boardwalk, from eateries like Off The Hook to a bandstand with live summer entertainment. Fenwick Island State Park has sprawling ocean views, and the nearby Fenwick Island Lighthouse, built in 1858, is also a favorite stop. The drive is about 30 minutes straight through, and can certainly be longer depending on the diversions.

Bombay Hook to Trap Pond

Here’s another unofficial byway, but this route showcases western areas of the state not found anywhere else and loved by nature lovers. It’s approximately 60 miles long, and the journey can begin either at Bombay Hook National Wildlife Refuge near Smyrna or from Trap Pond State Park near Laurel. If starting from the refuge, take Delaware 9 South, then merge onto US-13 South (Dupont Hwy). Keep an eye out for eagles, white-tailed deer, foxes, and hundreds of migratory birds while en route. Side expeditions could include the Parson Thorne Mansion in Milford, the community of Kitts Hummock, one of the best places in North America to see horseshoe crabs, or Dover, the state capital. If going straight through, allow for about 1.5 hours.

Miles Of Smiles

From covered bridges to lighthouses, beautiful estates holding treasures to marshlands teeming with wildlife, the First State offers plenty of miles and smiles. Whether you’re tracing history, following the coastline, or winding through quiet backroads rich in nature, each route offers a distinct glimpse into Delaware’s landscapes and heritage. Just pack up, pick one or more of these 8 suggestions, turn up the tunes, and enjoy!