Members of the Northwest Federation of Indians gathered in Penn Cove each August in the 1930s. The meeting included the International War Canoe Race, with 11 paddlers and a captain racing 50- to 70-foot-long canoes on a three-mile course.

This five-masted schooner was one of many ships that docked at Coupeville's 500-foot-long wharf in the late 19th century. Ships traded in lumber, wool, root crops, grain and apples.