The New Builders

CHAPTER SEVENThe Elephants in the Room

To stroll the Main Street in scenic Nantucket, Massachusetts, is to take a walk back in time. Uneven cobblestone pavers, a throwback to the town's early days in the 1600s as a whaling and commerce capital, bounce cars up and down as they make their way up the main business drag. Church spires peek out above the tops of the two‐ and three‐story buildings that line the street. Here and there, you catch glimpses of the town's historic waterfront.

Benches welcome those looking for a quick rest or a more extended stop to watch the tourists amble up and down the street, pausing to peer into shop windows in the slow, unhurried manner of people on vacation and with nowhere in particular to go. A monument to June Bartlett – the patriarch of the island's oldest farm – stands on the street's west side. The latest generation of Bartletts still sells produce and flowers from the back of a truck during the summers, something their family has done since the 1930s. Nantucket's Main Street has been a Historic District since 1955, and the style and type of buildings have been tightly controlled ever since (in fact, since 1971, the entire island has been a Historic District – something that at once brings the island its charm, but has also led to some of the nation's highest home prices).

Nantucket values its history and the role of entrepreneurs and small businesses in a way others talk about but few can turn into action.

In 2006, the town took the extraordinary ...