America’s Greatest Main Streets

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Bill Brooks / Alamy

Cheers to these small towns for great Main Streets, where you can admire architecture, sample the local flavor, and find a lost America.

Lahaina, HI

31 of 26

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.

Kate Appleton

America’s Greatest Main Streets

Lahaina, HI

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.

Kate Appleton

Bill Brooks / Alamy
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