Hammondsport earned its title as Americas Coolest Small Town, and the thing about it is that it actually lives up to the billing. This tiny village at the southern end of Keuka Lake — the only Y-shaped Finger Lake — has a picture-perfect village square surrounded by small shops, cafes, and a community that takes obvious pride in the place. It is the kind of town where you park once and walk everywhere, where strangers say hello, and where the pace of life slows down in a way that feels genuine rather than performed.

The Glenn H. Curtiss Museum is the towns cultural centerpiece and a genuine surprise for anyone who has not been. Curtiss was a Hammondsport native who pioneered early aviation and motorcycle racing — his contributions rival the Wright Brothers, and the museum does justice to the story with restored aircraft, engines, and local history exhibits. Beyond the museum, the village itself is the attraction: the square hosts seasonal events, the waterfront park offers swimming and boat access to Keuka Lake, and the surrounding hillsides are planted with some of the most important vineyards in the Finger Lakes.

This is wine country at its most storied. Dr. Konstantin Frank Vinifera Wine Cellars, just minutes from the village, is where European grape varieties first proved they could thrive in the Finger Lakes climate — a turning point for the entire regions wine industry. Pleasant Valley Wine Company, also nearby, is one of the oldest bonded wineries in America. The dining scene in Hammondsport is intimate but thoughtful, with restaurants and cafes that draw on the farms and producers in the surrounding hills. You will not find a long list of options, but what is here tends to be done with care.

Hammondsport connects to the broader Finger Lakes as a reminder of what the region looked like before the tasting rooms multiplied and the weekend crowds grew. It is still small, still quiet, still centered on the lake and the land. From here you can explore both forks of Keuka Lake, head south to Corning, or simply stay put and let the village do what it does best — make you wonder why you do not live in a place like this.