Long a favorite vacation destination for Rochester residents, this small city (population about 11,200) sits at the north end of 16-mi-long Canandaigua Lake. It was here that the 1794 Pickering Treaty was signed, brokering peace between the Iroquois and the U.S. government. Canandaigua's majestic courthouse, which still looms over Main Street, was the site of Susan B. Anthony's trial and conviction—she was found guilty of treason for voting in the 1872 election.
The wide main street with granite curbing is lined with stately Victorians in the north end of town. Heading south you pass through a downtown area with shops before you come to the lake. City Pier, which dates from 1847, is home to an eclectic mix of boathouses. Nearby Kershaw Park is a perfect place for a swim or a stroll.