Cape Elizabeth

Follow Route 77 through South Portland (sometimes called "SoPo") to reach the affluent bedroom community of Cape Elizabeth, where a detour along the two-lane Shore Road shows off the famed Portland Head Light and quite a few stunning oceanfront homes. A few minutes farther south is Cape Elizabeth Light, the subject of a well-known Edward Hopper painting.

Speaking of famous artists, Winslow Homer painted many of his famous oceanscapes from a tiny studio on the rocky peninsula known as Prout's Neck, a now exclusive gated community 7 miles south of Cape Elizabeth. The studio is open to tours only through the Portland Museum of Art; otherwise the public can access Prouts Neck only by parking outside the gates and walking along a popular cliff trail.