Photos/Montana Dennis

It was a cool October evening last week in Greenwich, Connecticut, and the trees along Perkins Drive still clung to their summer leaves, obscuring most of the gabled estates and gated manors along the road. This part of Connecticut, about 40 miles north of Manhattan, has a reputation for being the home to hedge fund managers, pro athletes and celebrities wanting to live outside the city—but not too far. In the middle of it all, the Burning Tree Country Club hosted one of the most exclusive cigar dinners of the season. And it raised nearly half a million dollars for charity. READ MORE