The sprawling city of Canandaigua has a wide and expansive feel. Through its center runs busy Main Street, a four-lane thoroughfare lined with leafy trees and imposing Greek Revival buildings set back from the street. At the foot of Main extends the lake and City Pier. Tourist-oriented businesses dominate.

Following the Revolution, two New Englanders, Oliver Phelps and Nathaniel Gorham, purchased what is now Canandaigua, along with the rest of western New York, from the Native Americans. The first white settlers arrived in 1789, and shortly thereafter, the first land office in the United States was established near present-day Main Street.

On November 11, 1794, the Seneca chiefs and Gen. Timothy Pickering met in Canandaigua to sign what was later known as the Pickering Treaty. A document of enormous significance, the treaty granted whites the right to settle the Great Lakes Basin. An original copy of the treaty can be found in the Ontario County Historical Society Museum.

During the summer, the Rochester Philharmonic Orchestra performs every weekend at the Finger Lakes Performing Arts Center (Rte. 364 and Lincoln Hill Rd., 585/325-7760), an outdoor amphitheater. Rock, jazz, and pop-music concerts are sometimes presented as well.

Recreation

The Canandaigua Lady (205 Lakeshore Dr., 585/396-7350) is a 150-passenger paddlewheel boat offering lunch, dinner, and moonlight cruises May–October. Captain Gray’s Boat Tours (5 Main St., 585/394-5270) features one-hour narrated tours of the lake daily July–August, weekends May–October; the boat leaves from behind the Canandaigua Inn on the Lake.

Seven miles northwest of Canandaigua lies Finger Lakes Gaming & Race Track (Rtes. 332 and 96, Exit 44 off I-90, 585/924-3232). Thoroughbred racing takes place Friday–Tuesday April–November. Also on site are 1,000 video-gaming machines.