32 miles E of Sandwich; 24 miles S of Provincetown

Sticking out like a sore elbow (and out of the way of much of the Cape's tourist flow), Chatham was one of the first spots to attract early explorers. Samuel de Champlain stopped by in 1606 but got into a tussle with the prior occupants over some copper cooking pots and ended up leaving in a hurry. The first colonist to stick around was William Nickerson, of Yarmouth, who befriended a local sachem (tribal leader) and built a house beside his wigwam in 1656. One prospered; the other -- for obvious and unfortunate reasons -- didn't. To this day, listings for Nickersons still occupy a half-page in the Cape Cod phone book.

Chatham, along with Provincetown, is the only area on the Cape to support a sizeable commercial fishing fleet -- against increasing odds. There's surprisingly little animosity between the hardworking residents and the summer vacationers at play, perhaps because it's clear that discerning tourist dollars are helping to preserve this lovely town.