Stop At The Most Beautiful Towns On The East Coast While Driving Down America's Oldest Highway

From adventure and self-reflection to lots of music, a road trip has it all. But your drive can be taken up a notch on the East Coast with the King's Highway, the ultimate ride that shows you history and charm. As the oldest road in America, the King's Highway stretches from Charleston, South Carolina, to Boston, Massachusetts, hitting Hampton, Philadelphia, Princeton, and New York along the way. From big cities to small towns, this road takes you everywhere.

Centuries ago, the King's Highway was the road to know — a 1,300-mile stretch that King Charles II of England ordered to be built between 1650 and 1735. It started out as a mail route, with post riders delivering letters across the colonies, before being upgraded to handle stagecoaches. Native American tribes used similar paths prior to the highway's development, trading and traveling along these routes. Fast-forward to modern day, and most of it is replaced by U.S. Route 1 and sections of U.S. Route 17.

The modern U.S. highway system owes much of its foundation to the King's Highway. Though that stretch looks much different, it doesn't mean you can't follow the same path, all the while encountering places on the road where the past and present coexist. 

If King Charles II ordered the highway to be built, it's only fitting that it starts in Charleston, which exudes a striking European appearance with Southern charm. The cobblestone streets take you back in time, while vintage carriages give a sense of nostalgia. Be sure to check out the Gibbes Museum of Art, which dates to 1905. Then, trade traditional transport for a quirky Bike Taxi around town.

Next, drive north toward Georgetown to admire the historic district and 18th-century Kaminski House. Don't miss the Prince George Winyah Episcopal Church — it's one of the oldest that still holds regular services in South Carolina. After Georgetown, make a stop in Edenton, North Carolina, a town known for its 18th-century architecture. If you happen to be there on a Saturday, check out the local farmers market — you just might find something tasty for the road ahead. Swing by the Chowan Arts Council, too, for a little dose of creativity and inspiration.

The journey is far from over — cruise through Yorktown, Virginia, and the beautiful towns of Annapolis and Baltimore in Maryland before continuing your trip to the City of Brotherly Love. Philadelphia, especially South Street, is a trendy melting pot of cultures and deserves its own separate trip. Princeton, home to the Ivy League institution Princeton University, is also on the way, so make time to stop there, as well.

The Big Apple is a 90-minute drive away, and you'll definitely want to spend a day or two here. Be sure to hit all the essentials — Central Park, the Empire State Building, the Metropolitan Museum of Art, and Rockefeller Center, especially during the holidays. Just remember not to fall for all those tourist traps at Times Square, like the creepy costumed characters. After that, drive on to Kingsbridge in the Bronx. While this may seem like a typical residential neighborhood, film buffs will recognize it from Martin Scorsese's "The Irishman." Then, head to Fairfield, Connecticut, where coastal views await. Whether you decide to watch the sunset at Jennings or Penfield Beach, the soothing shoreline will make it worth the stop.

Next up on the itinerary is New Haven, an unexpected pizza destination that could rival Italy itself. A feast for the eyes and the stomach, the culinary scene here is top-notch — you'll have the best quattro formaggio of your life at ​Frank Pepe Pizzeria Napoletana. Meanwhile, the mozzarella and tomato sauce pie at Sally's Apizza sets the standard for perfection. And just when you think you've eaten to your heart's content, it's time to wrap up the King's Highway adventure and chow down on clam chowder and lobster rolls at its terminus, Boston, which is hailed by travel personality Rick Steves as one of the best American cities to visit as a tourist.