The One Finger Lakes Town Everyone Should Visit At Least Once

Penn Yan is the kind of Finger Lakes town that earns its place on your itinerary right away. Set at the north end of Keuka Lake, this Upstate New York village pairs vineyard views, rolling farm country, and a walkable downtown. You can sample Riesling with sweeping bluff-top scenery at Keuka Spring Vineyards and follow the outlet trail past old mill ruins and rushing water at Seneca Mill & Falls. To sample the town's history, step inside the 1852 Oliver House Museum for a closer look at the town’s nineteenth-century past.

Add in nearby orchards, scenic drives along Routes 14A and 54, and quick access to the surrounding wine trail, and Penn Yan feels like a complete Finger Lakes getaway. Whether you are planning a road trip stop or a dedicated escape, it stands out as one of the region’s most rewarding places to visit.

A Cool Example of a Hard-Working Resort Town

Settled in the latter 1700s and incoprated in 1833 at the north end of Keuka Lake in Yates County, Penn Yan's unique name reflects the origins of its early settlers, many of whom came from Pennsylvania and New England. This included former East Coast dwellers often referred to as “Yankees.”

The village developed as a regional trade center serving farm operations in this incredibly lush part of New York, which in turn heavily shaped its early economy, particularly in grain, dairy, and later, vineyards, as grape growing rapidly expanded around the Finger Lakes. Penn Yan also became known for manufacturing, including flour mills and boat builders, like the Penn Yan Boat Company, which operated for much of the twentieth century.

It is a rare example of a town that continues to simultaneously be successful as a vacation destination and a hard-working, blue-collar community. The later arrival of rail connections only strengthened its role as a distribution hub, and over time, a budding tourism industry (also tied to the lakes’ gorgeous natural scenery and wineries) that supplemented agriculture as its primary economic driver.

What Makes Penn Yan's Landscape so Attractive to Both Tourism and Industry?

As mentioned, Keuka Lake is one of the major lakes in the Finger Lakes region of Upstate New York. However, its distinctive Y-shape sets it apart from the other long, narrow glacial lakes nearby, with the town itself lying along the outlet that drains Keuka Lake into Seneca Lake, placing it within a broader watershed that eventually connects to the Susquehanna River system.

The surrounding terrain consists of rolling hills formed by glacial retreat, leaving behind fertile soils that now support vineyards, orchards, dairy farms, and a number of state parks. Better yet for visitors and farmers alike, the lake does a good job at moderating local temperatures, extending the growing season, and reducing extreme winter cold compared to other inland areas.

Furthermore, Penn Yan’s position along State Routes 14A and 54 makes it a central access point for exploring wineries, scenic rural landscapes, and popular shoreline recreation destinations. With that, here are some of the best nearby attractions that you should definitely pay a visit to the next time you're in the area.

Keuka Spring Vineyards

Start off with one of the region's most famous local offerings at the Keuka Spring Vineyards, which sits on the western bluff of Keuka Lake just outside Penn Yan. It pairs its vintages with wide views over the water and hills, a perfect way to spend a summer evening.

Established in 1985, this institution produces estate-grown wines that showcase the by-product of the lake’s moderate climate and mineral-rich soils. Riesling and white blends are standouts, along with small-lot reds such as Cabernet Franc.

The open-air tasting area comes with picnic tables big and small, while seasonal events and vineyard tours provide a deeper dive for the region's viticulture, making it a solid stop for curious foodies along the Keuka Lake Wine Trail.

Seneca Mill & Falls

Seneca Mill & Falls is a striking natural and historic site just east of downtown Penn Yan. Located along the Keuka Lake Outlet Trail, the falls drop over layered shale and limestone, highlighting the glacial geology that originally shaped the Finger Lakes.

In the town's early days, the steady water flow helped power mills that supported its early businesses. But now, interpretive signage along the trail explains its longstanding industrial past while outlining the area’s ecological significance as well. Having a short, accessible walking path with idyllic views of cascading water, wooded banks, and remnants of former mill foundations, this is a nice little spot to visit year-round, especially during the fall when the area's foliage explodes with color.

Oliver House Museum

The YCHC Oliver House Museum preserves one of Penn Yan’s most prominent nineteenth-century residences. Built in 1852 for businessman Abraham Wagener, this Italianate home later became associated with the Oliver family, and now operates under the Yates County History Center.

Period furnishings, archival photographs, and rotating exhibits interpret much of Penn Yan's history for you, from early settlement and agriculture to industry and lake commerce/tourism. The house itself is a major part of the experience, with original woodwork, windows, and formal rooms stepping you back in time. Furthermore, regular guided tours will give you an even more detailed look into the families who once lived here and the broader development of Penn Yan and Yates County.

Other Worthwhile Towns and Villages Near Penn Yan

Beyond Penn Yan, several other Finger Lakes towns can add some greater depth to any road trip in the area. For example, at the northern end of neighboring Seneca Lake, the city of Geneva blends convenient waterfront access with another cozy downtown core. Here, you are free to walk the lakefront at Seneca Lake State Park, tour yet more nearby wineries along the Seneca Lake Wine Trail, or explore Hobart and William Smith Colleges, whose pleasant campus overlooks the water. Moreover, Geneva’s remarkable restaurant scene and historic district full of hotels and shops make it a practical base for exploring the eastern Finger Lakes.

South of Penn Yan, Watkins Glen is closely tied to none other than Watkins Glen State Park. The park’s narrow gorge, lengthy stone staircases, and series of waterfalls draw lots of traffic throughout the summer and autumn months. The town itself also hosts popular auto racing events at Watkins Glen International, making it a sought-after destination for car enthusiasts as well.

At the southern tip of Keuka Lake, Hammondsport boasts a smaller-scale setting but is likewise known for close-by vineyards and quiet lake views. History buffs should also be sure to drop by the Glenn H. Curtiss Museum, which highlights early aviation and local innovation.

Check Out this Welcoming Lakeside Town in New York this Year

From its verdant natural surroundings to its walkable lakeside core, Penn Yan is among the best Finger Lake towns to visit at any time of the year. It encompasses the best of what this distinctive region has to offer, whether it's world-class wineries, old-timey architecture, peaceful green spaces, or whatever else can be enjoyed in the countryside landscapes of Upstate New York.