2025's Most Underrated Towns In The Finger Lakes

Experience the delights of the Finger Lakes outside of the usual tourist towns at these underrated destinations. From historic downtown cores to quiet state parks and seemingly endless expanses of wineries, discover some of the best alternatives if you want to avoid the crowds in 2025.

Whether you are planning your summer vacation, a weekend getaway in the fall, or a wintertime escape from the big city, read on to see what options you have in this renowned part of upstate New York.

Penn Yan

Penn Yan sits at the northeastern tip of Keuka Lake and remains quite overlooked despite offering one of the most scenic and walkable downtowns in the entirety of the Finger Lakes. This village combines a 19th-century canal along the Keuka Lake Outlet with a highly accessible lakefront, making it very easy to connect with nature in the area as well.

You can either bike or walk the Keuka Outlet Trail, a wonderful path that follows an old railroad route past waterfalls and remnants of early industrial infrastructure. For a quieter experience closer to the lake, Indian Pines Park features public access for swimming, paddling, and picnicking.

In town, there are many other spots to explore, like the Arts Center of Yates County, which supports local artists with rotating exhibitions and workshops. In addition, the historic Sampson Theatre hosts community events on a regular basis. Moreover, Main Street includes a nice mix of mom and pop shops, bars, and restaurants, many housed in old brick storefronts.

This region is also lauded for its wine production. Nearby, vineyards like Keuka Spring and Fox Run offer tastings paired with unobstructed views of local lakes and the lush countryside around town.

Hammondsport

At the complete other end of Keuka Lake, Hammondsport houses a unique blend of convenient lake access, an important history in the world of aviation, and wine country charm without the congestion found in better-known Finger Lakes towns.

The historic district square, located right downtown, serves as the obvious central hub, lined with popular restaurants, bars, accommodations, and other amenities. For a more educational outing, the Glenn H. Curtiss Museum sits nearby, named after the aviation pioneer who was born in Hammondsport. It features a collection of aircraft, motorcycles, and other mechanical innovations that shaped early American aviation and ingenuity.

Water access in Hammondsport is easy, and Depot Park includes a public beach, a boat launch, and shaded picnic spots. Another way to see some natural sights is by hiking trails in Urbana State Forest, which is located a quick drive north of town and provides a secluded way to experience the woodlands of the Finger Lakes region.

While in the area, get a taste of local produce. A short trip just outside town will take you to Bully Hill Vineyards or the Dr. Konstantin Frank Winery, both of which provide lakeside tastings and an interesting look into the region’s winemaking legacy.

Dundee

Dundee rests between Seneca and Keuka Lakes. Though somewhat small, with a population of less than 1,700, this town is surrounded by family-run vineyards and other agricultural attractions for you to feast your eyes on. Hermann J. Wiemer Vineyard and Shaw Vineyard are both within easy reach and known for high-quality, small-batch wines along with great views near Seneca Lake, while numerous fruit stands and markets dot the nearby countryside.

For non-alcoholic treats, be sure to check out the Windmill Farm & Craft Market, where fresh-baked goods and local produce can be purchased. Moreover, seasonal farm stands and Amish markets along Route 14A offer direct access to local produce, baked goods, and hand-crafted furniture.

Downtown Dundee contains a handful of heritage buildings, including the Dundee Area Historical Society. A stay at the incredibly picturesque 1897 Beekman House Bed and Breakfast is worth trying. Its Victorian era style, inside and out, makes it one of the most charming bed and breakfasts in all of upstate New York.

Naples

Tucked at the southern end of Canandaigua Lake, Naples is yet another farm-focused town in this deeply rural region. Also like other towns in the area, it is best known for its grape-growing, which is showcased each fall during the Naples Grape Festival and year-round at local bakeries serving fresh grape pies. Must-see wineries nearby include Inspire Moore, Arbor Hill, and Randall-Standish Vineyards.

If you want something else to drink, this town is a hotbed for adult beverages of all kinds. Grab a beer at the Naples Brewing Company or Engine 14 Brewery. And for something a little stronger, Hollerhorn Distilling is a regional favorite, serving specially crafted spirits alongside delicious food at its onsite restaurant.

In terms of outdoor activities, the area’s terrain is steeper and more wooded than much of the Finger Lakes, attracting hikers to destinations like Grimes Glen, a short trail leading to two waterfalls and natural swimming holes. Better yet, this idyllic greenspace is barely a stone's throw outside of downtown.

Don't mind travelling a little farther? A few miles east is the High Tor Wildlife Management Area, which provides quieter, panoramic views from a number of naturally elevated points.

Trumansburg

Positioned just west of Cayuga Lake, Trumansburg offers quick and convenient access to several natural landmarks while also maintaining a distinct identity, separate from its much more visited neighbor, the city of Ithaca. It acts as a primary gateway to Taughannock Falls State Park, where a short trail leads to one of the tallest waterfalls in the eastern United States!

In town, the famous Trumansburg Farmers Market operates seasonally, while nearby wineries on the western Cayuga Lake Wine Trail, such as Sheldrake Point and Hosmer, are spots to go for tours and tasting experiences with views over the verdant countryside and the water. The town also hosts the long-running GrassRoots Festival, drawing a mix of folk and world music fans every July.

Get More Out of The Finger Lakes This Year

While places like Ithaca, Auburn, Watkins Glenn, and others are rightfully popular destinations in the Finger Lakes region, there is so much more to experience, particularly if you value avoiding crowds. These underrated towns are just a few ideas in terms of getting off the beaten path, whether you want to spend a summer day by the water or need somewhere to spend the night in 2025.