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Road Trip Itinerary from New York City to Virginia Beach

Picture of Leigh Hayhurst
Updated: 5 March 2018

Interstate 95 (I-95), one of America’s oldest, is the main thoroughfare that runs up and down the East Coast of the United States. Some of the major hubs along the way are Baltimore in Maryland, Washington, D.C., Wilmington in Delaware, Richmond in Virginia, and more. Before packing your bags and hitting the road, here are some of the must-see attractions to jot down on your itinerary, from New York City to Virginia Beach.

Philadelphia, Pennsylvania

Get to Independence Hall, birthplace of both the Declaration of Independence and the Constitution, early for a free ticket. To guarantee entry and avoid waiting in line, purchase a ticket online or by phone for $1.50 in advance. Grab lunch at Sonny’s Famous Steaks, located just steps away from the Liberty Bell, and enjoy an authentic Philly cheesesteak. Afterwards, stop by the infamous Eastern State Penitentiary, which once housed many of America’s most notorious criminals. Today the eerie, fortress-like structure is a crumbling historic landmark that allegedly receives visits from long-gone former inmates. Take a tour of the grounds and explore the empty guard towers, hallways and cell blocks but beware; you never know when you might feel an icy tap on the shoulder.


Independence Hall in Philadelphia, PA, the birthplace of the Constitution and the Declaration of Independence | © Skeeze / Pixabay

Baltimore, Maryland

Your next stop on I-95 is Baltimore, MD, and if you pass through during a baseball season, a visit to Oriole Park at Camden Yards to watch a game is a must. Oriole Park is a Major League Baseball (MLB) ballpark and home to the Baltimore Orioles. After the game, walk about a half mile to Inner Harbor. There you’ll find the Maryland Science Center, the National Aquarium, and Power Plant Live!, a former power station-turned-entertainment complex, offers food & entertainment, bars and music venues. Check out an unconventional institution: The Baltimore Tattoo Museum. Learn about the history of tattooing and see artifacts such as books, machines, tools, tattoo imagery and more. The museum doubles as an operating tattoo parlor, so you might just leave with a permanent souvenir!

Washington D.C.

Visiting the nation’s capital is an absolute must on your road trip to Virginia Beach. During your visit to D.C., explore Capitol Hill, walk by the White House and spend time in the world’s largest museum, the Smithsonian. Have a picnic lunch on the two-mile long National Mall or buy a hot dog from a street vendor. If it’s a rainy day, there are countless restaurants to choose from in the area. Relics at the International Spy Museum have been revealed to the general public for the very first time, so take a couple hours to explore the building and see devices of espionage, including cipher machines, counterfeit currency and weapons. For dinner, enjoy a nice dinner in Georgetown, one of the oldest neighborhoods in the district.


The White House is one of several must-see landmarks in Washington D.C. | gunthersimmermacher / Pixabay

Colonial Williamsburg, Virginia

Colonial Williamsburg is the the world’s largest living history museum, and was the center of political events leading to the American Revolution. Visitors can explore the perfectly-preserved 18th-century city today and get a glimpse of what life was like for America’s first settlers. Start at Market Square and begin your walk down Duke of Gloucester Street, the main road through town. Along your stroll you’ll see Colonial-style shops open to the public including a grocer, apothecary, bakery, and several full-service tavern restaurants. Actors donning 18th century attire walk the streets and play their parts as townspeople, soldiers, officials, shopkeepers and homemakers. For a meal, stop in one of the colonial taverns, or walk to Merchant’s Square where you can nosh on sandwiches, wine and cheese at The Cheese Shop; or try a traditional Welsh Rarebit from Dog Street Pub.


Experience what life was like for the earliest settlers in the U.S. in Colonial Williamsburg | © Humberto Moreno / WikiCommons