Discover the Scenic Routes from Chesapeake, Virginia to Darlington, Maryland

Are you ready for an adventurous road trip from Chesapeake, Virginia to Darlington, Maryland? Buckle up and prepare to embark on a journey filled with picturesque landscapes, charming towns, and unforgettable experiences. We've mapped out several routes for you to choose from, so you can take your time exploring and savoring the sights along the way. Get ready to hit the road!

The Scenic Coastal Route (230 miles)

If you're in the mood to enjoy stunning coastal views, the Scenic Coastal Route is perfect for you. This 230-mile journey will take you approximately 4 hours and 30 minutes, but trust us – the time will fly by as you soak up the beauty of the Atlantic Ocean. Departing from Chesapeake, follow Route 13 north, passing through quaint seaside towns like Cape Charles and Chincoteague Island. You'll also have the opportunity to explore the breathtaking Assateague Island National Seashore, a haven for wildlife enthusiasts and beach lovers alike.

The Historic Chesapeake Bay Route (160 miles)

For history buffs and architecture admirers, the Historic Chesapeake Bay Route is a must-try option. This 160-mile route will take you about 3 hours and 30 minutes to complete, but we recommend taking your time to visit the numerous historic sites and charming towns along the way. Head north on Route 17, crossing over the iconic Chesapeake Bay Bridge-Tunnel, an engineering marvel that spans 23 miles. As you continue, stop by the historic towns of Cape Charles, Eastville, and Salisbury, where you'll find beautifully preserved colonial architecture and cozy local cafes.

The Rural Countryside Route (200 miles)

If you prefer a more leisurely drive through scenic countryside, the Rural Countryside Route is for you. Covering approximately 200 miles and taking around 4 hours, this route will treat you to rolling farmlands, charming villages, and peaceful landscapes. Begin your journey by heading north on Route 13, and then take Route 460 west towards Suffolk. From there, enjoy the scenic drive through Suffolk, Wakefield, and Sussex, where you can take a break and visit some of the region's famous farmlands or indulge in delicious local produce at farmer's markets along the way.

Regardless of the route you choose, we recommend making a few pit stops to stretch your legs and discover some hidden gems along your journey.

If you're a nature enthusiast, consider visiting the Great Dismal Swamp National Wildlife Refuge, where you can hike through pristine wetlands and spot unique wildlife.
If you're a history lover, make a detour to St. Mary's Whitechapel, a charming colonial church dating back to the early 17th century, known for its stunning architecture and serene atmosphere.
If you're a foodie, take a break in Cambridge, Maryland, and savor some mouthwatering seafood dishes in one of the town's renowned waterfront restaurants.

Remember to check for any road closures or traffic updates before setting off, and don't forget to pack some snacks and your favorite road trip playlist. Enjoy every moment of your journey as you make your way from Chesapeake, Virginia to Darlington, Maryland. Safe travels and happy exploring!

Estimated driving times are based on average traffic conditions and may vary.