Keuka Lake Wine Trail & Hammondsport

Begin at the winery that changed what the Finger Lakes could grow — Konstantin Frank arrived from Ukraine in 1953 convinced the region could produce great vinifera wines (Riesling, Pinot Noir, Cabernet Franc) that others said were impossible in this climate. His family estate on the west bluff produces some of the Finger Lakes' most acclaimed bottles. The tasting room pours current releases with views down the steep vineyard slope to Keuka below.

Continue north on the bluff to Bully Hill, the famously irreverent winery founded by Walter Taylor after his family sold the Taylor Wine Company to Coca-Cola and barred him from using his own name — a story that produced some of American wine's most memorable label art and a museum of the feud. The hillside restaurant serves lunch (cheese plates, pizzas, sandwiches) above a panoramic sweep of Keuka's west branch.

Finish the afternoon at Heron Hill — the estate with Keuka Lake's most dramatic tasting room, a glass-walled pavilion cantilevered over the bluff with unobstructed views across both branches of the Y-shaped lake. The wines lean toward dry Riesling, Pinot Noir, and a strong Gewurztraminer, and the bistro pours by the glass alongside local charcuterie if you want to linger into the late afternoon light.

Dinner on the village square in Hammondsport — a convivial tavern that has been the town's social center since the 1800s, serving burgers, steaks, and local wine in a warm barroom facing the lakefront park.

Sleep in one of the Victorian-era B&Bs on the village streets of Hammondsport — a well-preserved lakeside village with covered porches, a small-boat harbor, and a quiet main square that rewards an early morning walk before the Glenn Curtiss Museum opens.

Explore the life of Hammondsport's most famous son — Glenn H. Curtiss won the first official air race in American history in 1908, built the first flying boat, and trained more early aviators than anyone else in the country. The museum houses original aircraft, motorcycles (he held the land speed record in 1907), and an honest account of his patent battle with the Wright Brothers, all in a well-curated space that doesn't require aviation obsession to enjoy.

A light lunch on the village square before the afternoon winery — sandwiches, soups, and coffee at one of the cafes facing the Hammondsport lakefront park.

Tour the oldest licensed winery in America outside California — Pleasant Valley received federal winery license #1 in 1860 and its stone cellars are still in operation. The tasting room pours sparkling wine and their flagship Great Western label in stone-vaulted rooms, and the self-guided cellar walk passes barrels and riddling racks unchanged in character since the 19th century.