Touring the Byway
5 Days / 4 Nights | Gateway City: Baltimore, MD

We recommend starting your journey in Baltimore, with a stop in the historic maritime town of Annapolis, on your way to the Historic Lewes Byway.  Explore the historic Main Street of this very old city, Annapolis Maritime Museum and Historic London Town and spend the evening in the Historic Inns of Annapolis.  

On Day Two, travel to Lewes, one of Delaware’s most beloved towns and the center of the Historic Lewes Byway. Start your visit here at the Lewes History Museum, which will put the rest of the stories told at historic properties into context.  From there, visit the Zwaanendael Museum and end your day relaxing and sipping at the Nassau Valley Vineyards.  

On Day Three, begin your visits at the Ryves Holt House, the Visitor Center of the Lewes Historical Society, followed by the Historic Architecture Walking Tour, on which you will hear the stories of important Lewes families and the historic homes they occupied over the past three centuries.  

From there, visit the Lewes Maritime Museum with its famous embedded cannonball, the Shipcarpenter Campus, encompassing 9 historic buildings, and the Life Saving Station (if open). 

Day Four gives you the opportunity to visit the Lightship Overfalls, the permanently moored 1938 lightship, and enjoy a Cape Water Tour, which will leave some time in the afternoon to explore the unique shops in downtown Lewes.  

Day Five begins with a visit to Cape Henlopen, including the Fort Miles Museum, where the “Great Dune” rises 80 feet above sea level and the “walking dunes” that move slowly across the pine forest.  From there, you can enjoy a scenic ride on the Cape May-Lewes Ferry, which has been making the 17-mile, 80-minute journey across the Delaware Bay since 1964. Fortunately, the ferry runs all up until 7:45PM to Cape May, NJ.

View the Detailed Itinerary below to see the full route, which is complete with dining, shopping,  and lodging recommendations!

Highlighted Attractions

Lewes History Museum

Start your visit to Lewes at the Lewes Historical Society which has been collecting thousands of artifacts, artwork, documents, maps and photos for over 50 years. A visit here will put your other visitors in context.  Ongoing exhibits begin with the founding of Lewes and continue with its maritime history, decorative arts and artists, famous families of Lewes, and how the region has been transformed through environmental change.

Lewes Maritime Museum

Nationally important pieces of maritime art and artifacts are on display in the 1765 Cannonball House that took incoming fire during the bombardment of Lewes during the War of 1812. It still holds the cannonball that nearly destroyed the historic structure.  Learn the story of the battle, the maritime history of the region, and the story of Gilbert McCracken and his son Henry, who continued to defend Lewes until the end of the war in 1815.

Historic Shipcarpenters Campus

Nine historic buildings highlight Lewes’s relationship to the sea and illustrate the  three centuries since its founding.  The Campus includes the 1720 Hiram Rodney Burton House, the only building on its original site, the 1785 Burton-Ingram House, illustrating fine Federal period architecture and original furnishings, the 1740 Rabbit’s Ferry House which illustrates life in rural southern Delaware, the 1800 Thompson Country Store,  the 1790 Ellegood House another Sussex County farmhouse and Blacksmith Shop, the 1850 Doctor’s Office, and 1898 Midway School #178.

Annapolis Maritime Museum and Park

The historic McNasby Oyster Company, the last oyster packing plant in Annapolis serves as the home of the Annapolis Maritime Museum.  With a direct view of the Chesapeake Bay, the campus includes the exhibits center, three transient piers, an adjacent beachside park with wooden boat exhibits and kayak launch point, a research library and a rotating, maritime-themed art gallery

Lewes Historical Society Architecture Walking Tour

For a great introduction to Lewes, following your drive here, the Lewes Historical Society offers a Historic Architecture Walking Tour through the National Historic District which encompasses 122 contributing buildings and 6 contributing sites within the 17th-century core of the town.  The district is primarily residential with resources ranging from small working-class houses to large and ornate houses from the Victorian period in Queen Anne and Second Empire styles. The Market Street commercial area, includes three frame store buildings and the elaborate Smith Block. Other buildings include St. Peter’s’ Episcopal Church, the Ellis Marine Complex, Cannonball House, Governor Ebe W. Tunnell House, Walsh Building, Zwaanendael Museum, Cornelius Burton House, Lewes Historical Society enclave, and the De Wolf Houses.

To experience all that The Gateway to the Bayshore has to offer, download the complete itinerary!

The detailed itinerary includes: