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John Lagano working on a boat at the Greenwich Yacht Club on Grass Island.
Greenwich's coast has been known as a haven for vacationers and playground for the wealthy, and those who are able to take advantage of the shoreline have one of the most infamous politicians to thank.

In 1860, a few colleagues of William Marcy "Boss" Tweed, the leader of New York's powerful Democratic Party political machine, Tammany Hall, were sailing on Long Island Sound and sought refuge from headwinds on Round Island on the western shore of Greenwich Harbor south of Grass Island. According to published accounts, they reported their find to Tweed, who brought his New York friends back to the spot for the summer.

Tweed eventually founded the Americus Club, a posh playhouse and forerunner to the modern-day country club, where he and his political cronies reportedly drank and played billiards, ate meals prepared by French chefs and were served by hundreds of attendants.

The club was based on the tip of the peninsula that separates Indian Harbor and Smith Cove, eventually the site of the former Indian Harbor Hotel, which was torn down in the 1890s and replaced with a three-story waterfront mansion built by New York banker E.C. Benedict.

Tweed -- who earned his reputation for political corruption by stuffing ballot boxes, and was convicted for stealing millions from New York City taxpayers, dying in jail at age 55 -- introduced a whole new society to Greenwich. Aside from the Americus Club, Tweed bought 80 acres on what is now East Putnam Avenue and built

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a summer mansion, contributing to local charities. He "correctly predicted that within a couple of decades the town would be adorned by the mansions of millionaires," reads a section on Tweed in "Greenwich: An Illustrated History."

Tweed also introduced "sophisticated maritime activities" to the town, said Anne Young, archives curator for The Historical Society of the Town of Greenwich. He encouraged yachtsmen to race, and even created a steamboat company in 1866 for New York commuters that eventually went out of business.

"He really is the first New Yorker to really entice New Yorkers to come to Greenwich," Young said. "You go where the power is."