The One Upstate New York Town Everyone Should Visit At Least Once

The Finger Lakes host some of the most welcoming and charming locales across New York State. This distinct upstate region is home to a series of elongated bodies of water created during the Ice Age that, from a high vantage point, somewhat resemble a series of long human digits.

Extremely lush during the warmer months and a perfect setting for both farms and cottages, these lakes attract crowds of vacationers every summer and fall. While not everyone has the privilege of owning a lake home, the various communities within often provide all the amenities you should need for a fantastic weekend (or longer) outing.

That's what brings us to Hammondsport, a quaint village of less than 600 residents that rests on the southern end of Keuka Lake. Despite its small size, Hammondsport offers a range of overnight accommodations, shopping areas, historic landmarks, and other attractions worth checking out at least once!

A Quick History of Hammondsport

Hammondsport draws its history back to the late 1700s, not long after the country's founding, when settlers were drawn to the south end of Keuka Lake for its fertile land and natural harbor. The village was laid out in the coming decades by Lazarus Hammond, whose name it still bears, and by 1829, the first vineyards (of which the region is now famous for) were put in the ground. Hammondsport then quickly became a notable transportation and trade hub, shipping agricultural goods and timber harvested from local woodlands along the lake and connecting to regional markets by canal and rail beyond.

Incorporated officially in 1871, its most technically influential chapter began later in the budding days of the 20th century with the rise of the airplane. In fact, the town is still closely tied to Glenn H. Curtiss, a pioneer of early flight and naval aviation. Curtiss established aircraft and engine operations nearby, transforming it into a center for manufacturing just in time for the First World War. His work earned him international recognition and permanently linked Hammondsport to the history of technology.

These days, with a vast selection of vineyards, cool museums, pristine parklands, and a longstanding downtown core, Hamonsport and its surrounding landscapes have become a significant tourist draw. Here are some must-visit attractions the next time you're in the area.

Glenn H Curtiss Museum

As you can imagine, the Glenn H Curtiss Museum is probably Hammondsport’s most significant attraction and a cornerstone of the village’s identity. Located just outside downtown, the museum preserves the story of Glenn H. Curtiss, a notable name in aviation and early motorcycle engineering.

Exhibits include a restored aircraft, early engine models, motorcycles, and seaplanes that showcase Curtiss’s role in shaping flight, naval aviation, and motor manufacturing in general. A series of detailed displays boasts fun interactive exhibits, and rotating collections add depth for repeat visitors. Furthermore, the museum’s lakeside setting near Keuka Lake shows off the connection between Curtiss’s experiments, water-based aircraft, and the picturesque region that supports his enduring legacy to this day.

Finger Lakes Boating Museum

On the other hand, the Finger Lakes Boating Museum offers a more focused look at the region’s deep connection to water-based travel. Also located just outside of Hammondsport's main core, this museum showcases an impressive collection of vintage and historic boats built for the Finger Lakes, from early wooden runabouts to classic racing and pleasure craft.

Through photographs, tools, and preserved vessels, the Boating Museum documents how boating culture evolved alongside the Finger Lakes in a digestible manner that can be enjoyed in an afternoon. Its numerous exhibits give attention to local boatbuilders, the history of the lake's tourism sector, and the role boating played in shaping lakeside communities, while restoration workshops even allow you to see traditional craftsmanship in action!

Depot Park

Depot Park sits directly along the Keuka Lakefront and serves as downtown Hammondsport’s most popular public space. The park occupies the site of the village’s former railroad depot, a reminder of Hammondsport’s role as a transportation stop. Today, it features lots of open green space, picnic areas, and a lakeside walking path with clear views across Keuka Lake.

Its central location near shops, restaurants, and the waterfront further makes Depot Park an easy stop for anyone exploring the town on foot. Moreover, seasonal events and community gatherings are often held here, especially during the summer months.

Embark on a Wine Tour

For wine enthusiasts who want an escape from busier grape-growing regions, the area around Hammonsport is simply heavenly. Well over a dozen good wineries are within reach, from simple tasting rooms downtown to sprawling vineyards in the countryside. Many of these vineyards are open for tours, personalized tastings, and other events, and given their proximity to town, you can easily hit up multiple in one day.

Nearby options include Living Roots Finger Lakes, Keuka Lake Vineyards, Heron Hill Winery, and Dr. Konstantin Frank Winery (a local favorite). On the other side of Keuka Lake, Weis Vineyards and McGregor Vineyard are other top-notch spots. You also ought to drop by the Finger Lakes Wine Museum beside Bully Hill Vineyards to learn more about the agricultural history of this beautifully delicious region.

Staying in Hammondsport

Hammondsport and the surrounding Keuka Lake area host a variety of overnight accommodations that suit a variety of travel styles and budgets. In the village proper, a handful of charming bed-and-breakfasts, full of small-town character, also have walkable access to shops, restaurants, and the waterfront. Some favorites include 18 Vine Inn & Carriage House and the Blushing Rose Bed & Breakfast. Moreover, a few local small motels and inns, namely the Village Tavern Restaurant & Inn, offer straightforward and comfortable stays.

Around Keuka Lake, several lakeside resorts and vacation rentals offer scenic views and water access at all times, appealing to those seeking a truly picturesque experience. Wineries and farms nearby often host guests too, especially during the peak summer and colorful fall foliage seasons. Cottages and cabins around the lake are popular for families and groups.

Other Ideal Towns Nearby

If you can't book anything in Hammondsport, you also have the option to stay in other attractive Keuka Lake towns like Penn Yan, a regional hub that offers many of its own museums, wineries, and a great food scene.

For something a bit smaller, the community of Wayne sits nearby on Waneta Lake. The primary source of overnight accommodations here is in the form of rental cottages, with only a few other amenities within walking distance, making it perfect for a peaceful weekend.

The city of Bath is another option for those seeking a larger town to explore. Located just south of Hammondsport along the Cohocton River, it too has its own diverse selection of hotels, locally owned eateries, and cool attractions for the whole family to enjoy in a waterfront setting.