The Most Charming Towns in New York's Finger Lakes

Aerial of Skaneateles Lake in Springtime
Matt Champlin / Getty Images

Totaling 11 long, narrow lakes in west-central New York, the Finger Lakes are an outdoor and culture paradise with extensive hiking trails, hundreds of wineries, fascinating historical sites, and breathtaking gorges. For many, the bustling college city of Ithaca is the gateway to the region. Yet, there are many more hidden gems, adorable downtowns, and experiences tucked throughout the Finger Lakes' most charming towns and villages. 

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Watkins Glen

Watkins Glen State Park

TripSavvy / Makito Umekita

Positioned on the southern tip of Seneca Lake, Watkins Glen is a popular destination for its natural beauty, access to surrounding wineries, and quaint downtown, though the nearby Watkins Glen International racetrack may have broader name recognition. Aside from race day, visitors flock to Watkins Glen State Park for the stunning series of waterfalls cascading through its deep limestone gorge. Of the three trails, the two-mile Gorge Trail is recommended for letting hikers meander through the beautiful gorge along stone paths, across bridges, and behind waterfalls. Meanwhile, downtown Watkins Glen holds plenty of local restaurants and specialty shops along N. Franklin St. Here you’ll also find the Seneca Harbor Wine Center, where you can sample local vintages and craft a plan for visiting some of the 31 wineries on the Seneca Lake Wine Trail. To get the most from Watkins Glen’s lakefront splendor, the Harbor Hotel is a sure bet. 

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Aerial of Small Village on Lakeshore in Autumn
Matt Champlin / Getty Images

Skaneateles is located on the north end of 16-mile Lake Skaneateles—the second most easterly of the 11 lakes comprising the Finger Lakes region. Strolling the town’s lakefront and main thoroughfare, Jordan Street, leads past numerous galleries, eateries, and historic homes. Stopping by famously “not famous” Doug’s Fish Fry is a must for seafood lovers. Dine in or take a shrimp po boy or lobster roll to go and picnic at Clift Park, where you’ll find picturesque views and a designated swimming area. Due to Skaneateles’ higher elevation and limited development, the lake water is the cleanest among the Finger Lakes. Skaneateles Lake may not boast the wineries of its western neighbors, but Skaneateles Brewery and Last Shot Distillery are on hand for sampling local brews and spirits and exploring the neighboring Charlie Major Nature Trail. To avoid confusion and being exposed as an out-of-state newbie, take note that Skaneateles is actually pronounced “skinny-atlas” or “skanny-atlas.”

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Canandaigua Boathouses
Chris Achtschin / Getty Images

Although it’s technically a city with roughly 10,000 residents, Canandaigua exudes small town charm. Canandaigua sits on the northern end of Canandaigua Lake—the fourth largest in the Finger Lakes. Downtown features numerous bars, restaurants, and shops along Main Street. From here, side streets lead you by historic Victorian homes and public parks, the most notable being 50-acre Sonnenberg Gardens & Mansion State Historic Park. The immaculate gardens, greenhouse, 40-room mansion, and onsite Finger Lakes Wine Center are open to the public, and guided tours are offered.

Nearby at Ontario County Park, hikers, cyclists, and cross-country skiers can pick up the Ontario Pathways trail, which extends roughly a dozen miles to the Town of Phelps. On the return trip, a stop for a local brew at Bee Hive Brew Pub is well-deserved. More recreation opportunities await at Canandaigua’s lakefront, including swimming at Kershaw Park and exploring Canandaigua City Pier. Built in 1848, the pier draws artists and photographers for its picturesque boat houses. The rustic house-like structures are for boat storage only and are preserved as part of the Canandaigua Historic District. To extend your stay, there are a wide selection of bed and breakfasts in and around Canandaigua, such as the farmhouse-chic 1837 Cobblestone Cottage

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USA, New York, Exterior
Walter Bibikow / Getty Images

Hammondsport is scenically situated amid rolling hills on y-shaped Keuka Lake’s southern end. The village of just 622 people features a pair of breweries and seven wineries amid a downtown core of galleries, cafes, and shops. Hammondsport also holds claim to the Finger Lakes' first winery, Pleasant Valley Wine Company, which has been producing wine from Catawba grapes since 1860. Other noteworthy vineyards include Heron Hill, Dr. Frank’s Vinifera Wine Cellars, and Bully Hill Vineyards. The latter’s onsite Greyton H. Taylor Wine Museum lets visitors dive into the history of winemaking while sampling local vintages. Renting a kayak or paddleboard from Keuka Kayak is a great way to explore the third largest finger lake and overcome a lingering wine hangover. If you’re planning to stick around for a while, the Black Sheep Inn is conveniently set just west of downtown and offers an impressive all vegan menu and uniquely styled rooms in a 19th-century octagonal home. 

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Cayuga lake
DebraMillet / Getty Images

The Village of Aurora sits in the heart of the Finger Lakes on Cayuga Lake’s eastern shores. The entire village, which spans less than one square mile, is listed on the National Register of Historic Places and includes the campus of Wells College. As such, many relics from the past are in immaculate shape today, largely thanks to restoration efforts by Pleasant Rowland—the founder of the American Girl doll brand and Wells College alumnus. Despite its size, Aurora packs plenty to fill an itinerary. A quick stroll along elm-lined Main Street takes in the Aurora Farmers’ Market, Lake Glass Beach, and historic homes. Just outside the village limits, Long Point State Park is another popular swimming spot and Long Point Winery is a worthy stop on the Cayuga Wine Trail for its dry Riesling and red zinfandel. To further appreciate the village’s history, spending a night or longer at the Inns of Aurora will do the trick. The resort spans five inns, each of which occupy a historic residence and are unique in their architecture and design. 

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Like Canandaigua, Geneva is actually a city. Yet, its charming town square and walkable downtown give it a real small-town feel. The array of innovative eateries, breweries, and bars is substantial for a city of just 13,000 residents. Exchange Street features several blocks of local shops and restaurants, but narrow Linden Street is the heart of Geneva’s culinary scene. When the weather cooperates, the street is closed off to on weekends to traffic, allowing patrons to drink and dine alfresco. The Linden Social Club is renowned for their cocktails, while the Rusty Pig is a fan favorite for its craft brews and barbecue. When school is in session, students from Hobart and William Smith Colleges further energize the nightlife. The Smith Center for the Arts is another perk of local academia. The 1,400-seat venue showcases a stacked schedule of theatrical performances, concerts, and films. Positioned on the northern tip of Seneca Lake, Geneva enjoys lovely waterfront views and ample recreation opportunities too. A 2.5-mile trail connects downtown to Seneca Lake State Park, a serene spot for a picnic, hike, or a refreshing swim in the deepest of the Finger Lakes. 

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Taughannock Falls State Park in Finger Lakes region upstate New York
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Situated about 20 minutes northwest from Ithaca, Trumansburg flies somewhat under the radar to visitors outside the region due to its inland location between Cayuga and Seneca Lakes. For those in the know, however, T-burg is a vibrant community with year-round festivities and access to some of the Finger Lakes most striking landscapes, namely Taughannock Falls State Park. Although the park offers stellar lakefront views, the crown jewel is the 215-foot falls that cascade through the magnificent gorge. Back in town, Main Street houses a charmingly eclectic array of storefronts and businesses, including craft beer at Garret’s Brewing and farm-to-table fare at Hazelnut Kitchen. In the summer months, the village celebrates with concerts and performances at Porchfest and the Finger Lakes Grassroots Festival of Music and Dance. The latter includes dance and music workshops, local vendors, and a happiness parade where attendees are encouraged to show off their effervescence in stride with stilt walkers, musicians, and jugglers. 

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