Canandaigua High Roads · Italy Valley

Curves and lake in the Finger Lakes: from Naples you take Italy Valley Rd, the technical part, drop to Middlesex and ride NY-364 up the east shore of Canandaigua Lake to the city. You return on West Lake Rd and NY-21 down the west side to Naples. It's 56 miles that mix a string of curves with high views over the lake. Fuel in Naples or Canandaigua. Italy Valley Rd packs 20-plus curves into about six miles, so take it easy.

Canandaigua Lake is about 15.5 miles long, 1.5 wide and 276 feet deep at most, and its name comes from a Seneca word usually translated as "the chosen spot." It's the only source of drinking water for the city and town of Canandaigua and several towns around them. Its one small island, renamed Skenoh Island in 2021, is the smallest Fish and Wildlife Management Area in New York.

Italy Valley Rd, the technical start of the ride, packs 20-plus curves into about six miles. Naples calls itself the Grape Pie Capital of the World and has held its grape festival every September since 1961; in 2026 it ran September 26 and 27. On the way back south, the Lake View Point overlook in South Bristol has a free lot and picnic tables high above the water.