20 Oakland, Maryland
Oakland has small-town charm all wrapped up in a pretty package. But this slow-paced Maryland hamlet has just the right amount of bustle downtown to keep things vibrant. There are bountiful boutiques, art shows, parades, live music, and unique dining spots. If you're lucky enough to find yourself in Oakland in Autumn, you can enjoy the annual explosion of fall foliage in a kaleidoscope of colors.
