The farthest west of the major Finger Lakes, Canandaigua Lake is also the most commercialized. Rochester (pop. 235,000) is less than 30 miles away, and the lake has served as the city’s summer playground since the late 1800s. At the northern end of the lake lies the historic city of Canandaigua, now largely a resort town. At the southern end rests the trim village of Naples.

Canandaigua is Iroquois for “The Chosen Place,” and according to legend, the Seneca people were born at the south end of the lake, on South Hill. As the legend goes, the Creator caused the ground to open here, allowing the Seneca to climb out. All went well until a giant serpent coiled itself around the base of the hill.

Driven by an insatiable hunger, the snake picked off the Seneca one by one until at last a young warrior slew him with a magic arrow. The dying serpent writhed down the hill, disgorging the heads of its victims as he went; large rounded stones resembling human skulls have been found in the area.

Heading south down Canandaigua’s eastern shore, you’ll pass through a series of picturesque valleys. At the southern end of the lake, the route skirts around South Hill and the High Tor Wildlife Management Area (585/226-2466). Hiking trails traverse the preserve, which is also one of the few places left in New York where you can still spot bluebirds—the state bird. The main entrance to the area is off Route 245 between Middlesex and Naples. South Hill is now part of the Hi Tor Wildlife Management Area.

Also connected with the Seneca is tiny Squaw Island, located in the northern end of the lake. The Seneca people relate that many women and children escaped slaughter by hiding out here during General Sullivan’s 1779 campaign.