The town centers of Kennebunk and Kennebunkport are separated by 5 miles and two rivers, but united by a common history and a laid-back seaside vibe. Perhaps best described as the Hamptons of the Pine Tree State, Kennebunkport has been a resort area since the 19th century. Its most recent residents have made it even more famous: the dynastic Bush family is often in residence on its immense estate here, which sits dramatically out on Walker's Point on Cape Arundel. Newer homes have sprung up alongside the old, and a great way to take them all in is with a slow drive out Ocean Avenue along the cape.
Sometimes bypassed on the way to its sister town, Kennebunk has its own appeal. Once a major shipbuilding center, Kennebunk today retains the feel of a classic New England small town, with an inviting shopping district, steepled churches, and fine examples of 18th- and 19th-century brick and clapboard homes. There are also plenty of natural spaces for walking, swimming, birding, and biking, and the Kennebunks' major beaches are here.