Upper Marlboro is a tiny town found on less than one square mile, but the surrounding cities have over 850,000 people. The history dates back to Colonial times, which is why it’s the seat of Prince George County. It’s also been home to many respected figures like a Maryland State Senator and a U.S. Congressman. It’s far from the “city that never sleeps,” but it does offer quaint attractions and is close to the Washington D.C. Metro Area, if you crave more action.