8 Most Scenic Road Trips to take in Delaware

Delaware is a small slice of the East Coast of the United States, but it merges three distinct personalities into a tight package. The waters of Delaware Bay and the North Atlantic Ocean define the Eastern border, a green, minimally-populated countryside takes over from there, and dazzling estates from some of the nation's richest families sprout up sporadically to capture the imagination. Get to know the first official state (established in 1787) in the most American way possible – a good old-fashioned road trip. These drives do not eat up many miles, but they are savory, scenic, and intellectually stimulating. 

Delaware Bayshore Byway

The Delaware Bayshore Byway was designated as a National Scenic Byway by the United States Department of Transportation in February of 2021. It is the longest road trip on this list – not just packed with scenic miles, but also a dense tapestry of attractions. This 100-mile highway offers a less-trafficked, slower-going way to descend from the original capital of New Castle, in the far North of the state, alongside the Delaware River, to as far South as the old shipbuilding town of Milton. Along with these two historical places, tourists will encounter 17 other "Discovery Zones" that highlight the coast's natural beauty, biodiversity, early colonial history, as well as the cultures of the Lenape and Nanticoke nations, and other cute, lunch-break-worthy small towns. Even with lots of rose-smelling stops, 100 miles can go by in a flash. So to continue the road trip even further, consider heading slightly East to Lewes and the next scenic drive on our Delaware journey. 

Historic Lewes Byway

The tour through the town of Lewes combines a lovely atmosphere with more early-American history. The Historic Lewes Byway is short but sweet and best experienced at a slow pace. Passengers will pass 300-year-old sites, the beaches of Delaware Bay and maritime waterfront, bird sanctuaries, and the Atlantic Ocean-teasing, outdoor-recreation-promoting Cape Henlopen State Park (which houses the World War II era Fort Miles, as well as more popular beaches) throughout the 13-mile trip. The byway, or more accurately, a selected network of roads, constitutes New Road, Pilottown Road/First Street, Savannah Road, Kings Highway, Gills Neck Road, and Cape Henlopen Drive. When all is said and done, park the car and add some miles on foot around town to better appreciate the flavors of a town founded back in 1631. 

Brandywine Valley National Scenic Byway

Another Delaware roadway that has been honored with the national scenic byway status is the brief, tuning-fork-shaped Brandywine Valley route. Though spanning only 12.25 miles through New Castle County, this road trip presents a choose-your-own-adventure split that can be doubled back on in order to get the full experience. Brandywine Valley National Scenic Byway begins in downtown Wilmington, which sits immediately North of New Castle and therefore begs to be linked with the Delaware Bayshore Byway, and heads North-Northwest to the Pennsylvania border via either Route 100 (i.e., the Eastern arm) or Route 52 (the Western arm). Many opulent estates and perfectly-groomed gardens can be ogled en route, including those of the famous du Pont family. Route 52 is also a section of another amazing journey, the Harriet Tubman Underground Railroad Byway.

Harriet Tubman Underground Railroad Byway

This road trip commemorates the brave journey of the freedom-seeking slaves (particularly the eponymous "conductor"), and the abolitionist allies that made safe passage possible. While the drive certainly passes through beautiful parts of the country, it is, first and foremost, an exploration into a beacon of light from a dark period of American history. The Delaware section of this multi-state byway spans approximately 95 miles (depending on which loops are taken), accepting the baton from Maryland on Willow Grove Road in Kent County, and relaying North to the Pennsylvania border, merging with the Route 52 portion of the Brandywine Valley National Scenic Byway in the final stretch. Along with the enshrined "depots" that offered refuge to the runaway African captors and other interpretive sites, some of the more scenic stops include Blackbird State Forest, First State Heritage Park, and the Old State House museum. 

Nanticoke Heritage Byway

Relax into a rural small-town setting on this 35 to 40-mile, somewhat circuitous stretch through the Western portion of Southern Delaware's Sussex County. The Nanticoke Heritage Byway begins from US 13 at the Route 20 exit to Bridgeville Road and casually works its way to Trap Pond State Park. Along the way motorists will have a chance to stretch their legs and experience a glimpse of the laid-back life for the residents of Seaford, Bethel, and Laurel. Other highlights include the historic mansions en route, the crossing of the Nanticoke River via the Woodland Ferry, and a pleasant stroll through one of North America's largest strands of bald cypress trees in Trap Pond State Park.  

Laurel To Deal Island (Maryland)

Speaking of the small Sussex County town of Laurel, an unofficial road trip can be from here to another quaint spot in Maryland. By combining US-13 (South) and MD-363 (West), for a total of 45 miles, motorists will find themselves in the Historic District of Deal Island. This timeless fishing town sits on a 3-mile-long island surrounded by the waters of Tangier Sound – an offshoot of Chesapeake Bay. On the way in and out of town, Deal Island Road passes through the Deal Island State Wildlife Management Area – an expanse of wetlands that is great for spotting birds, particularly waterfowl. This side trip explores an overlooked part of Delaware and lets travelers check off another state. 

Red Clay Valley Byway

The 27-mile-long Red Clay Valley Byway pieces together 28 secondary roads in New Castle County – specifically the Red Clay Creek watershed region between Routes 48 and the ever-more-familiar Route 52. The hour or so of straight driving can easily be extended with vista photo-ops and forest bathing. In terms of the latter, stop to stretch your legs at the Red Clay Ravine Natural Area, smell the roses (and other native plants) at the Mt. Cuba Center botanical garden, or explore the 4-mile trail network through the 130 acres of woodlands and meadows at the Ashland Nature Center. Take a few more pictures at the bright red Ashland Covered Bridge, and lastly, spend some time appreciating the world's largest collection of operating steam cars at the Auburn Heights Preserve. 

Bethany Beach To Ocean City (Maryland)

Another unofficial itinerary that will be particularly appealing for aquarius souls, especially in the summer. This short excursion connects two coastal towns – Bethany Beach, the quiet Delaware hangout, to the Maryland resort town of Ocean City. Each place brings a different energy, and the entire 15-mile drive on DE-1/MD 528 is sandwiched between the Atlantic Ocean and Little Assawoman Bay, Assawoman Bay, and Isle of Wight Bay, in that order from North to South. Enjoy the intimate beach vibes of the Northern terminus for a day, then scoot down to the lively boardwalk and 14-mile stretch of sand in the cool Maryland hub for a change of pace. 

The First State is a delightfully drivable place. Traffic is light, friendly towns dot the backroads and byways, the scenery changes regularly, and history leaps off the landscape. There is no need to guzzle gas in Delaware, for everything is close by. But cut the engine regularly anyway in order to take in the sounds of the rolling waves, enjoy a pleasant walk through tranquil forests, or engage with the historical sites, museums, and interpretive centers that break up many of the scenic byways.