The Setting

Hammondsport sits at the base of Keuka Lake’s south end, where the two branches of the Y-shaped lake merge into a single body of water. The village is small — about 700 residents — and compact enough to walk from one end to the other in 10 minutes. The center of town is a village square with a gazebo, a fountain, old trees, and surrounding storefronts that house shops, restaurants, and tasting rooms. It looks like the town square that Hollywood set designers dream about but can never quite get right because no one believes places this charming actually exist.

But Hammondsport is not just quaint. It has two legitimate historical claims. First: this is where the commercial wine industry in the Finger Lakes began, with the Pleasant Valley Wine Company (now Great Western) established in 1860. Second: Glenn Curtiss, the aviation pioneer who rivaled the Wright Brothers, was born here and built his first aircraft in town. The combination of wine heritage and aviation history gives Hammondsport a depth that most small Finger Lakes villages lack.

Morning: The Village Square and Coffee

Start on the square. Park in the free lot behind the shops (Sheather Street) or on the street around the green. Parking is never a problem in Hammondsport — this is not Geneva or Ithaca.

Walk the square’s perimeter. The buildings are a mix of 19th-century commercial storefronts and newer construction that respects the village’s scale. Small shops sell local crafts, wine accessories, and gifts. The Hammondsport Public Library, in a handsome stone building, faces the green.

For coffee, Crooked Lake Ice Cream Company on the square serves espresso drinks and baked goods alongside their homemade ice cream. In the morning, coffee and a pastry on the patio overlooking the green is a civilized start. If you want a more substantial breakfast, the Village Tavern on the square does eggs, pancakes, and breakfast sandwiches.

Mid-Morning: The Glenn H. Curtiss Museum

The Glenn H. Curtiss Museum is on Route 54, about a half-mile north of the village square. It chronicles the life of Glenn Curtiss, who built and flew the first aircraft sold commercially in the United States and won the first international air race (the Gordon Bennett Trophy in 1909 at Reims, France). Curtiss also developed the flying boat and trained the first naval aviators.

The museum houses restored aircraft, motorcycles (Curtiss was also a champion motorcycle racer — he once held the land speed record), vintage boats, and local history exhibits. The collection is well-curated and genuinely interesting even for visitors who are not aviation enthusiasts. The museum’s restoration shop, where volunteers rebuild antique aircraft, is visible through a glass wall.

Plan for 60 to 90 minutes. Adult admission is around $12. Open daily from May through October; Thursday through Sunday in winter. The museum also offers biplane rides from the adjacent airstrip in summer — about $50 per person for a 15-minute flight over Keuka Lake. If you have never seen the Finger Lakes from a biplane, this is a singular experience.

Lunch

Return to the village square for lunch. Options include:

Village Tavern: A solid American restaurant on the green. Burgers, sandwiches, salads, and a few more ambitious entrees. The outdoor patio in warm months is the best lunch seat in town. Local beer and wine on the menu. Moderate prices — $12 to $18 for a lunch entree.

Crooked Lake Ice Cream Company: Sandwiches and lighter fare alongside the ice cream. Good for a quick lunch if you want to maximize time for afternoon wine tasting.

Keuka Brewing Company: A brewpub with an outdoor area and food trucks on busy weekends. Craft beer brewed on-site with views toward the lake. A relaxed option.

Afternoon: Keuka Lake Wineries

Hammondsport is the southern anchor of the Keuka Lake Wine Trail, and several tasting rooms are within a 15-minute drive. The wine trail here is less trafficked than Seneca Lake’s, which means shorter waits, more personal attention, and a quieter tasting experience.

Dr. Konstantin Frank Vinifera Wine Cellars (5 min. north on Route 54): Arguably the most historically important winery in the Finger Lakes. Dr. Frank, a Ukrainian immigrant, proved in the 1950s and 1960s that European grape varieties (vinifera) could survive upstate New York winters — a breakthrough that transformed the region’s wine industry. The winery continues to produce excellent dry Riesling, Gewurztraminer, Rkatsiteli, and sparkling wines. The tasting room overlooks the lake, and the staff is well-informed. Tastings run $10 to $15.

Bully Hill Vineyards (5 min. north on Route 76): The wild card of Finger Lakes wineries. Founded by Walter S. Taylor, who was famously litigious and even more famously eccentric, Bully Hill has a museum of wine-label art, goats on the property, and a tasting room that feels more like a roadhouse than a winery. The wines are sweet-leaning but unpretentious. The restaurant, with lake views, serves lunch daily in season. If you want serious wine, go to Dr. Frank. If you want a good time and a burger with a view, go to Bully Hill.

Heron Hill Winery (10 min. north on Route 76): A beautiful hilltop property with a tasting room designed like an Arts and Crafts lodge. Heron Hill makes the most of its location — the view from the tasting room deck, looking north across Keuka Lake, is one of the best winery views in the Finger Lakes. Their Rieslings and Ingle Vineyard designates are excellent. Tastings $10 to $15.

Pleasant Valley Wine Company / Great Western: The oldest commercial winery in the Finger Lakes, located just north of Hammondsport. The stone cellars, built into a hillside in the 1860s, are worth a tour for the historical value alone. The wines today are modest, but the setting and history are significant.

Late Afternoon: The Lake

After wine tasting, drive back to Hammondsport and head to Champlin Beach at the south end of Keuka Lake. The beach is public, free, and has a small parking lot, a patch of sand, and calm, shallow water. In summer, this is where locals swim. The south end of Keuka is sheltered by hills on three sides, so the water is calmer here than on any other Finger Lake.

If you brought a kayak (or rented one from Keuka Watersports near the beach), an evening paddle from Champlin Beach north along the eastern shore is spectacular. The vineyard-covered hills catch golden light in the late afternoon, and the water is often glassy by early evening.

Evening

Return to the village square for dinner at the Village Tavern or drive 10 minutes to one of the winery restaurants (Bully Hill or Heron Hill, if their dinner hours align). End the day with a scoop of homemade ice cream from Crooked Lake Ice Cream Company — their grape flavor, made from local Concord grapes, is the quintessential Finger Lakes dessert.

Getting to Hammondsport

Hammondsport is about 20 minutes north of Corning and the Corning Museum of Glass, 30 minutes southwest of Penn Yan, and 50 minutes west of Watkins Glen via Route 54. From the New York State Thruway, the nearest exits are Exit 38 (Canandaigua) or Exit 42 (Geneva), each about an hour’s drive. The village is small and walkable once you arrive.

For more on the area, see our Keuka Lake Wine Trail guide, the Keuka Outlet Trail, and our Keuka Lake guide.