9 Cutest Small Towns In The Finger Lakes For 2025

Nature strikes a soothing note at the Finger Lakes, a tranquil, swoon-worthy region where liquid mirrors glimmer and shimmer with iridescent coyness. You will find Pinot Noirs and Chardonnays, verdant valleys and trout-rich streams, as well as quiet forest trails and sun-dappled ridges. Several charming small towns dot this underrated slice of New York, home to a picturesque grouping of eleven narrow glacial lakes. But which are the cutest? Starting with Trumansburg, discover below the 9 cutest small towns in the Finger Lakes for 2025.

Trumansburg

With a Main Street that resembles a picturesque corridor featuring a cohesive collection of eye-catching Italianate structures with decorative cornices, Trumansburg effortlessly makes other towns look average. Gimme! Coffee, a hallowed name right on Main Street, has an outdoor patio next to a lazy creek and serves fresh, made-to-order coffee in a wonderful setting. Catch an afternoon show at the iconic Trumansburg Conservatory of Fine Arts, Inc. (TCFA), an 1851 landmark listed in the National Register of Historic Places. Taughannock Falls State Park is just a hair out of town, and is one of nature's most astounding handiworks. It is home to the tallest free-falling waterfall east of the Mississippi. On the opposite side is the Finger Lakes National Forest, a tranquil green space ideal for both hunting and hiking.

Penn Yann

In a country where several main streets are completely overrun with big box retailers and strip mall developments, Penn Yann is a wonderful breath of fresh air. It is poised for even a better look, especially considering it recently won a $10 million Downtown Revitalization Initiative. Keuka Lake Outlet flows through Main Street and makes the whole stretch a tad more rustic and romantic. A beautiful multi-use trail of the same name runs along the water and presents a rosy, peaceful view of the surrounding landscape. Pass by Seneca Farms, a Finger Lakes culinary highlight defined by three words: Homemade Ice Cream. After this, spend some time at Indian Pines Park, a lovely space by the lake with a swimming area and sugary views.

Aurora

Previously called Peachtown, for the beautiful peach orchards prevalent in the area, and Deawendote, a Native word for “the village of constant dawn,” Aurora is an escape into a gentler, more heavenly side of New York. When European settlers arrived, they named this postcard beauty for the Roman goddess of the dawn. Main Street runs along Cayuga Lake, a glimmering gem that offers soft, reflective sunrises. If you are spending the night, The Inns of Aurora is a collection of historic homes thoughtfully restored to blend nostalgia with a streak of modern taste and style. There is the 1833 Kitchen & Bar, where a view from the patio, especially at sunset, will make for an unforgettable evening. Walk around the campus of Wells College Golf Course and take in the beautiful views on every side. You can also enjoy a delicious meal at the beautiful clubhouse or an epic round of golf on a well-maintained course.

Hammondsport

Hammondsport may be small and demure, but it is in a scenic area that revolutionised winemaking in the United States. After centuries marked by failed attempts to introduce Vinifera to colder climes, Dr. Konstantin Frank, an enterprising Ukrainian national, successfully developed the most well-known grape variety in the world and from which we get our Pinot Noirs, Cabernet Sauvignons, and Chardonnays. The flavours at the Dr. Konstantin Frank Winery will hit your taste buds with a bang and can surprisingly turn out to be the highlight of your trip. There is Champlin Beach, where you can rest on the grass and enjoy delicious views, and Depot Park, which has benches for relaxing and admiring Keuka Lake.

Skaneateles

If Norman Rockwell were to be presented with three New York small towns to paint, it is difficult to imagine he would omit Skaneateles, a stunning time capsule that reclines on the northern shores of the eponymous lake. Skaneateles is a wealthy village, and the upscale ambiance is hard to miss. You will find rocking chairs on front porches, a handsome Main Street with architecture that dates as far back as the 1790s, and a waterfront locale with heart-ravishing views of the surrounding scenery. Spend a few hours at the Skaneateles Historical Society, which tells the story of the area in several creative ways, and Clift Park, a swoon-worthy space with heart-melting waterfront views. You will want to stay at Sherwood Inn, an iconic property in the heart of town with a history that goes back to 1807.

Naples

A nature lover’s mecca in a landscape that features dramatic hills and quiet deciduous forests, Naples is named for its chaotic and cultured European counterpart, an exuberant Italian town that doubles up as one of the oldest continuously inhabited urban areas in the world. You will instantly fall in love with Naples, New York, with its grape pies and rolling vineyards; with its artsy spirit and rustic feel. Bristol Valley Theater on Main Street, an iconic performance venue in a 125-year-old building, often brings in top talent from New York City and all around the country. The Naples Grape Festival, which lights up the town every year in September, features what is billed as the "World's Greatest Grape Pie Contest." Talking of grape pies, Cindy's Pies presents a whole new world of tongue-tingling flavors that should never be missed. But you will love the delicate pastries at Monica’s as well.

Geneva

Geneva is tastefully positioned on the northern rim of Seneca Lake, the "lake trout capital of the world." But avid anglers are not the only lot that will love the town’s home-grown culinary scene, the stunning canopies of Linden Street, or the deepest of the Finger Lakes. Everyone around here knows about the Belhurst Castle and Winery. The 1880s landmark is loved for its Old-World charm, unique architecture, and beautiful lake views. It has previously been voted one of the Most Romantic Places in New York State. The Rose Hill Mansion is a time-kissed beauty that provides a glimpse into the town’s childhood years. The on-site tour takes about an hour, but it will certainly be time well spent. Start with coffee at Monaco's, and amble through Washington Street, before snapping some pics at the soul-stirring Finger Lakes Welcome Center.

Montour Falls

If there is one feature that makes Montour Falls look like something plucked straight out of a fairytale, it is the dramatic 165-foot waterfall that cascades right into its incredibly handsome downtown. Shequaga Falls is lily white, musical, and sassy. You will hardly find such a fizzy gem in the heart of a town. Taking the cue, Eagle Cliff Falls is a cool, secluded place with a serenading cascade and million-dollar views. The last thing on your mind here will be those irksome bills that create drudgery out of life. What's more? Turn the wheels of time at Brick Tavern Museum - Schuyler County Historical Society, a riveting spell of surrogate time travel. And don't skip the on-site gift shop that keeps cool and affordable works by talented local artists.

Ithaca

Ithaca is fairly big and home to a modest population of about 32,000 residents, but was there a place that looks so genuine and personal like Ithaca? Home to Cornell University, one of the best in the world, you should expect a top-tier cultural scene with an exuberant dining and entertainment landscape. Still, with its dramatic gorges and waterfalls, you will be blown away by the heart-gripping scenery that defines almost every open space. Start with some finely prepared sushi at Asia Cuisine, a 21-year-old establishment at the corner of Aurora and Buffalo Streets. Afterward, take some time to tour Cornell, whose stunning campus hosts several world-famous attractions, including the Cornell Botanic Gardens. You will find plenty of comfortable benches on which to sit and breathe in the clean, fragrant air. There is also the mind-bending Ithaca Falls Natural Area, which, in winter, often transforms into a magical, icy spectacle.

The Takeaway

Are you looking for a dreamy, small-town escape where lush vineyards meet glimmering lakes with unusually narrow shapes? Far from the noise and chaos of downtown Manhattan, you will find a cornucopia of charming small towns, some of which are the most beautiful in America. Think of winding Main Streets with age-old facades, cozy cafes beside lazy creeks, and tranquil parks with lovely waterfront views. And if you want a place where time slows as wine flows, you are in luck. The Finger Lakes Region is home to several picturesque wineries, some of which shaped and redefined the nation’s viticulture.