America's Greatest Main Streets
Bill Brooks / Alamy
Front Street has seen all kinds of action since the early 1800s: Hawaiian royals who briefly made their capital here; tavern-hopping whalers; missionaries; and adventurers seeking their fortune in this balmy Maui town. Thanks to community efforts, it's still dominated by evocative two-story wooden buildings with wraparound balconies. Inside, many businesses now cater to tourists looking for coral necklaces, artwork, and fruity cocktails at sunset. Whale-watching tours depart in season, not far from an enormous banyan tree—and favorite photo-op—that faces the courthouse.
Worth a Stop: The Wo Hing Museum at 858 Front St., once a cultural center for Chinese plantation workers. Compare their island life with the experiences of a missionary family who lived nearby at the restored Baldwin House.