Canandaigua is the most approachable lake in the region: smaller wine trail, less traffic, and a downtown that works without wine-trail branding pressing down on it. The Treaty of Canandaigua was signed at the north end in 1794 and is still honored annually on November 1. Come in late September for the Naples Grape Festival, or any other time when you want to experience the quieter side of the Finger Lakes.

The Seneca Nation are Ondöndowa’ga:', the Great Hill People. Their origin story places the emergence of their people at Nundawao, the Great Hill, at the lake’s southern tip near Naples. The name of the lake comes directly from Seneca: Tganondæ:gwęh, the Chosen Spot. Fifteen miles northwest, near Victor, is Ganondagan, the Town of Peace, which at its 17th-century height was one of the largest Seneca towns, home to roughly 4,500 people.

Jikonsaseh, the Mother of Nations, whose diplomatic intervention was essential to founding the Haudenosaunee Confederacy, lived here and is buried nearby. The French destroyed Ganondagan in 1687, burning 150 longhouses during the fur trade conflicts. The Seneca rebuilt their political life elsewhere, absorbing further losses during the Sullivan-Clinton Campaign of 1779, and returned to the treaty table in November 1794.

In November 1794, more than 1,500 Haudenosaunee representatives gathered at Canandaigua. The Seneca had invited a delegation of Quakers from Philadelphia to witness. On November 11, fifty-nine sachems signed the Treaty of Canandaigua. The treaty affirmed Haudenosaunee sovereignty, set Seneca territorial boundaries, and established a framework for resolving disputes. The United States still pays the annual cloth annuity promised in Article Six. The original parchment is held by the Ontario County Historical Society at 55 North Main Street. The Haudenosaunee return each November 11 to brighten the chain of friendship. The ceremony is open to the public.

The Canandaigua Lake Wine Trail has nine producers running from Victor and Fairport south through Canandaigua and along the lake’s western ridge to Naples, thirty miles end to end. The south-end cluster around Naples is the most food-integrated wine loop in the region: wineries, grape pie, and a gorge walk all within thirty minutes of each other.

What distinguishes the Canandaigua expression: lighter body, more fruit-forward, a tasting culture that tends toward approachability. The south end, where the valley compresses and the Concord-planted hills are dense, produces wines that prioritize agricultural character over formal structure. For visitors new to the region, this is often the right lake to start with before heading east to Keuka or Seneca.

Honest note: Canandaigua’s nine producers and Seneca Lake’s thirty-three sit at opposite ends of trail ambition. Canandaigua is a day trip. Seneca is a two-day project. Both are worth doing.

Start at Sonnenberg Gardens in Canandaigua for the Finger Lakes Wine Center overview, then drive south on Route 21, stopping at Heron Hill on the western ridge in South Bristol. Continue south to Naples for Arbor Hill, Hazlitt, Inspire Moore, and Hometown Wine Company. Return north on Route 64 past the South Bristol Overlook. One day, no backtracking. Tasting fees $10–$15 per stop. Full hours May through November; call ahead December through April.

Canandaigua’s outdoor geography is organized vertically: the lake at the floor, the vineyard ridge running the western wall, and the gorge at Naples tucked into the south end. Gannett Hill at 2,256 feet is the highest point in Ontario County. The lake itself offers steamboat cruises on a 19th-century replica paddleboat from the city pier.

The Concord grape defines the Canandaigua valley’s agricultural identity. Route 21 south from Canandaigua to Naples is one of the most productive fruit-growing corridors in the Finger Lakes. The Concord is native to this climate in ways that European vinifera is not, and the variety that makes Naples grape pie taste like nothing else in the country.

The name is Seneca. Tganondæ:gwęh, the Chosen Spot, rendered as Canandaigua, which is what happens to a language when colonial administrators try to write it down phonetically in English. The Seneca Nation were the ones who named it, and they had been here long enough to know what they had found. The glacial lake runs 15.5 miles south from the city at its northern end into a valley that narrows as it approaches Naples, where the hills press in close and the Concord grape harvest defines September in a way that nothing else in the Finger Lakes quite matches.