6 Prettiest Small Towns In The Finger Lakes

The Finger Lakes region of Upstate New York is one of America's most distinctive geographic features. Looking from space like outstretched fingers spread north to south across the landscape between Rochester and Syracuse, these 11 glacier-carved lakes have evolved into one of the Northeast’s top tourist destinations for their natural beauty and pretty small towns.

The best of these towns aren’t only pleasant to look at, they’re also hotbeds of cultural activities that draw visitors from across the state and beyond. Add to this their stellar food and drink scenes, their attractive old downtowns, as well as their warm and friendly locals, and it’s easy to see why these six small towns in particular are considered some of the best places to visit in the Finger Lakes.

Skaneateles

Sitting at the northern tip of Skaneateles Lake, picturesque Skaneateles is considered by many to be the prettiest small town in the Finger Lakes. Named after the Iroquois word meaning "long lake," Skaneateles is especially popular for its attractive Victorian-era architecture. As you stroll along Genesee Street, look out for the elegant old Sherwood Inn. Established in 1807 as the town’s original stagecoach stop, it still offers top-notch accommodations. The nearby Skaneateles Antique Center is another must-visit, this time for collectors and browsers alike.

The town's most photographed landmark is its pretty Skaneateles Lake waterfront. Highlights include a municipal pier where you can cast a line or hop aboard a fishing charter with Lucky Buck Fishing. You can also get out onto the water by renting a pontoon boat or kayak from the friendly folks at Skaneateles Marina, just a few minutes south of town, or take scenic cruises aboard the Judge Ben Wiles, a restored 1907 steamboat operated by Mid-Lakes Navigation.

The best time to visit? Shoot for the Skaneateles Festival. Held each August, it transforms the lakefront into an outdoor concert venue featuring chamber music performances set against the backdrop of the lake. For accommodation, the historic Sherwood Inn offers lakefront rooms, while the pretty Mirbeau Inn & Spa provides a more contemporary luxury experience with its French-inspired architecture and full-service spa.

Watkins Glen

Positioned at the southern tip of Seneca Lake, Watkins Glen serves as a great base from which to explore one of New York State's most spectacular natural attractions: Watkins Glen State Park. Here, the Glen Creek has carved a dramatic 200-foot-high gorge through Devonian shale and sandstone, creating 19 cascading waterfalls. The two-mile-long Gorge Trail will get you to the best of them, including Rainbow Falls, the 60-foot Cavern Cascade, and the towering Central Cascade.

Downtown Watkins Glen centers around Franklin Street, the historic downtown core. After exploring the state park (it’s accessible off Franklin Street), head north toward the lake past iconic buildings such as the Glen Theatre to Senecas Harbor Park for spectacular views of the lake. Along with the state park, it’s one of the venues for the FLX Summer Fest at The Glen, a food and drink festival that attracts thousands to sample wines from regional wineries.

For lodging, the Watkins Glen Harbor Hotel provides superb lake views, while the Colonial Inn & Creamery is within easy walking distance of the state park entrance.

Hammondsport

Known as the "Cradle of Aviation" for its connection to aviation pioneer Glenn Curtiss, Hammondsport occupies a prime position at the southern end of Keuka Lake, the only Y-shaped lake among the “Fingers.” You can best experience its pretty 19th-century architecture along Shethar Street and the Hammondsport Historic District. Encompassing 52 contributing buildings dating from 1860 to 1930, highlights include Pulteney Square, undoubtedly one of the prettiest old public squares in Upstate New York.

Although a little outside of town, the Glenn H. Curtiss Museum showcases the achievements of the man who made the first official public flight in America in 1908. It’s also home to an impressive collection of vintage aircraft, motorcycles, and the restored 1918 Curtiss JN-4 "Jenny." The Keuka Lake Wine Trail is a great way to combine sightseeing with some winery tours. A highlight is visiting Dr. Konstantin Frank Winery, founded in 1962 by the pioneer who proved European grape varieties could thrive in the Finger Lakes climate.

Accommodations include the Keuka Lakeside Inn, a Victorian-era property offering rooms with lake views, and the Black Sheep Inn & Spa, a boutique-style B&B set in a unique octagonal mansion dating from 1859.

Penn Yan

Named after Pennsylvania Dutch (Penn) and New England Yankees (Yan) settlers, Penn Yan’s location at the northern tip of Keuka Lake makes it an ideal spot to indulge in some good old-fashioned Upstate New York hospitality. The star attraction is the pretty Penn Yan Historic District. A delightful place for a stroll, highlights include the 1873 Yates County Courthouse, a fine example of Second Empire architecture with its distinctive mansard roof and ornate stonework. The Oliver House Museum, operated by the Yates County Genealogical and Historical Society, is a must-visit and occupies a Greek Revival mansion built in 1852.

Other to-dos include visiting The Birkett Mills, founded in 1797 and still producing stone-ground buckwheat flour (it’s one of the oldest continuously operating businesses in the Finger Lakes). For accommodations, the Wagener Estate Bed & Breakfast offers rooms in a restored 1890 Victorian-era mansion.

The town's location on Keuka Lake provides access to some of the Finger Lakes' most scenic waterfront, including Keuka Lake State Park. In addition to its 621 acres of rolling hills, mature forests, and mile-long shoreline, the park's camping facilities serve as a base for fishing enthusiasts targeting the lake's population of lake trout, salmon, and smallmouth bass.

Canandaigua

Named for the Seneca word Kanandarque, meaning "the chosen spot," Canandaigua certainly lives up to its origins. Situated at the north end of Canandaigua Lake, the community’s pretty downtown features one of the most intact collections of 19th-century commercial architecture in the Finger Lakes region. Among its most impressive structures is the Ontario County Courthouse, built in 1858 in Greek Revival style with a prominent columned portico. Just a short stroll away, Sonnenberg Gardens & Mansion State Historic Park is a 50-acre estate created in the 1880s with nine formal gardens along with a spectacular turreted mansion.

Canandaigua Lake ranks as the fourth largest of the Finger Lakes and maintains a reputation for excellent fishing, particularly for lake trout and landlocked salmon. The City Pier serves as a focal point for summer activities and provides access to the Canandaigua Lady, a replica 19th-century paddle-wheeler offering dinner cruises and sightseeing tours. Kershaw Park, established in 1925, features a natural sandy beach, picnic facilities, and a historic boathouse.

July’s Canandaigua Art & Music Festival presents classical and chamber music performances in venues throughout the city and is a great time to visit. If planning to make a weekend of it, historic hotels like the Inn on the Lake (1911) and the more modern The Lake House on Canandaigua book up early.

Geneva

Geneva occupies a strategic position at the northern tip of Seneca Lake, the largest and deepest of the Finger Lakes. Its location made it a crucial transportation hub during the 1800s when the Seneca and Cayuga Canal connected it to the Erie Canal system, fostering economic growth that’s still evident in the grand architecture along South Main Street. The pretty Geneva Historic District features over 200 contributing buildings, including the ornate Smith Opera House, built in 1894 and continuing to present live theater, concerts, and film screenings.

Hobart and William Smith Colleges also contribute significantly to Geneva's cultural life, as well as its architectural landscape. Campus highlights include Trinity Hall from 1837, and the Scandling Campus Center, built in 1925. Be sure to also explore the town's Lakefront Park with its mile-long walking path and interpretive signs explaining the area's geological history and Native American heritage. For those wanting to get out on the water, Seneca Lake State Park provides public access with a marina, boat launch, and swimming area. Consider yourself a wine buff? The Seneca Lake Wine Trail includes over 30 wineries within a 20-mile radius of Geneva.

For accommodations, the spectacular Geneva On The Lake resort offers luxury rooms in a 1910 Italianate villa overlooking Seneca Lake. Alternatively, the 41 Lakefront Hotel provides modern amenities, easy lake access, and its own beach area.

The Final Word

The Finger Lakes region’s smallest towns represent some of New York State's most compelling places to visit. If you’re looking for a place where natural beauty combines with rich history to create unique travel opportunities, these communities are guaranteed to satisfy day-trippers, road trippers, and weekend warriors alike. And as travel to Upstate New York continues to increase in popularity, these six pretty towns in the Finger Lakes will keep on providing the kind of unique and authentic travel experiences people are longing for.