Exploring America’s 250th: Historical Road Trips to Ocean City, Maryland

• Baltimore: Fort McHenry National Monument
• Cambridge: Harriet Tubman Museum 
• Berlin: Historic Downtown 
• OC: Walking the Boardwalk / OC Foodie Tour

Begin your journey at Fort McHenry, the birthplace of the national anthem and a powerful symbol of Baltimore’s role in the War of 1812.  As you head east on Route 50, you will enter Cambridge located along the Harriet Tubman Underground Railroad Byway. Here, the Harriet Tubman Museum honors her legacy and provides insight to her lasting impact. Almost to OC, you will reach the Historic Downtown of Berlin frequently recognized as one of “America’s Coolest Small Towns.” Take time to wander through the streets with beautifully preserved Victorian buildings, local shops, and inviting restaurants. Just minutes later, Route 50 delivers you straight into Ocean City. Settle in and wrap up your road trip with a walk along the historic boardwalk, where landmarks like the Atlantic Hotel and longtime favorites such as Dolle’s Candyland tell the story of the town’s early resort days. Pair your stroll with a foodie tour highlighting the classic OC flavors, then unwind and enjoy your stay by the sea!

• Philadelphia: Independence Hall 
• Dover: The Old State House / John Dickinson House
• Cape Henlopen to Fenwick: WWII Towers
• OC: Art League of Ocean City

Start the road trip in Philadelphia at Independence Hall, where the Declaration of Independence and the U.S. Constitution was debated and adopted, anchoring the trip in the birthplace of American democracy.  Leaving the city, head south and cross into Delaware where you will move into Dover. Step back into the colonial era at The Old State House and John Dickinson’s Plantation. These sites highlight Delaware’s role in the nation’s founding and the life of John Dickinson, one of the Founding Fathers. As you continue through Delaware, the landscape opens up along the shoreline from Cape Henlopen to Fenwick where there are various World War II observation towers that once guarded the coast. Arriving in Ocean City, explore the town’s creative side at the Art League of Ocean City. Founded in 1963 by a group of local artists, the Art League has grown into a cultural cornerstone, celebrating the community’s artistic heritage through exhibitions, classes, and events. It’s a fitting way to end your journey but start your stay in OC – where history, culture, and creativity come together. 

• Richmond: St John’s Church
• Norfolk: Hampton Road Naval Museum
• Pocomoke: Delmarva Discovery Museum / Shad Landing
• Snow Hill: Furnace Town Living Heritage Museum
• OC: Museum of Ocean City

*Crisfield: J. Millard Tawes Historical Museum

In Richmond, you will head to St. John’s Church, where Patrick Henry delivered his famous “Give me liberty, or give me death!” speech, marking a pivotal moment in the American Revolution. From here, travel southeast towards Norfolk. As you arrive, stop by the Hampton Roads Naval Museum located along the waterfront which highlights the area’s long standing naval presence and its role in American military history. Continuing north along the eastern shore, you’ll cross into Maryland and reach Pocomoke, where the Delmarva Discovery Museum and nearby Shad Landing at Pocomoke River State Park showcase the region’s natural history, waterways, and working landscapes that have shaped life on the shore for generations. Just up the road in Snow Hill, step back in time at Furnace Town Living Heritage Museum. This restored 19th-century village brings early industrial life to life, offering a glimpse into how ironworking and trade supported communities across the region. Complete your journey in Ocean City with a visit to the Museum of Ocean City. Located downtown in a former bank, this museum has the history of the building, exhibits about historic people, places, wildlife, and businesses that shaped the town to what it is today. An ideal final stop before relaxing on your vacation.

* A worthwhile detour takes you to Crisfield and the J. Miliard Tawes Historical Museum. Though a slight detour once you enter Maryland, Crisfield offers a deeper look into Maryland’s Eastern Shore culture, seafood heritage, and the communities that have long depended on the Chesapeake Bay.

• Washington DC: National Museum of American History
• Annapolis: U.S. Naval Academy
• St. Michaels: Chesapeake Bay Maritime Museum
• OC: Ocean City Life-Saving Station Museum

Begin the journey in the capital of the U.S. at the National Museum of American History, where the stories, objects, and innovations that shaped the nation are all in one place. From Washington DC, head east towards your first stop in Annapolis, home to the U.S. Naval Academy. Stroll the historic campus and waterfront, where naval tradition and maritime history have defined the city for more than a century. Continuing across the Chesapeake Bay and to the eastern shore, make your way to St. Michaels and the Chesapeake Maritime Museum. This waterfront destination offers an in-depth look at the bay’s working history from boat building to watermen’s traditions that still influence life on the shore today. From here, it’s a straight drive to Ocean City where the journey of marine history comes full circle at the Ocean City Life-Saving Station Museum. Located at the end of the Boardwalk, the museum highlights the bravery of early surfmen and the town’s origins as a seaside refuge. Once you learn about the past, then you can enjoy the present and relax in paradise!