11 Weekend Escapes To New York State’s Hidden Finger Lakes Towns

The Finger Lakes region of New York State is a treasure trove of charming small towns, stunning lakes, and vineyard-covered hills that many travelers overlook. These peaceful communities offer perfect weekend retreats from busy city life, with their combination of natural beauty, local cuisine, and rich history. Whether you’re a wine enthusiast, outdoor adventurer, or simply seeking a quiet escape, these hidden gems deserve a spot on your travel list.

1. Skaneateles’ Pristine Blue Waters

Pronounced ‘skinny-atlas,’ this elegant village graces the northern shore of its namesake lake, which Native Americans called ‘long lake.’ Skaneateles boasts some of the cleanest water in the country – so pure that Syracuse once used it unfiltered for its municipal supply.

The village exudes upscale charm with its Federal and Greek Revival mansions lining the shore. Boutique shopping on Jordan and Genesee Streets offers everything from artisanal foods to unique clothing. For a truly special experience, book a meal at Rosalie’s Cucina, a beloved Italian restaurant with Tuscan flair.

Lake activities abound, from the vintage mail boat cruise to kayaking the crystal waters. Winter brings the enchanting Dickens Christmas celebration, transforming the village into a Victorian-era wonderland.

2. Penn Yan’s Amish Country Gateway

Horse-drawn buggies sharing roads with cars isn’t uncommon in Penn Yan, a community where modern life meets Mennonite and Amish traditions. This working-class town at Keuka Lake’s north end serves as the perfect base for exploring both wine country and simpler ways of life.

The Keuka Outlet Trail, following an old railroad bed, offers a scenic 7-mile path for hiking or cycling between Keuka and Seneca Lakes. Local restaurants like Seneca Farms serve legendary ice cream and fried chicken that draws visitors from miles around.

For authentic Amish goods, venture to the nearby countryside where roadside stands sell homemade quilts, furniture, and fresh produce. The Windmill Farm & Craft Market, operating since 1987, gathers over 200 vendors every Saturday.

3. Naples’ Purple Pie Paradise

Tucked into the hills at Canandaigua Lake’s southern end, Naples has earned fame for its grape pies – a unique regional delicacy you’ll struggle to find elsewhere. Every September, the Naples Grape Festival celebrates the harvest with wine tastings, crafts, and plenty of those famous pies.

Beyond grapes, Naples offers exceptional outdoor adventures. Nearby Grimes Glen invites hikers to wade through creek beds to reach two beautiful waterfalls. The Bristol Hills branch of the Finger Lakes Trail provides more challenging terrain for serious hikers.

Art thrives in this creative community, with numerous galleries showcasing local talent. For a perfect Naples day, grab breakfast at Grandy’s, hike the glen, then relax with a wine tasting at Inspire Moore Winery, housed in a restored 1870s barn.

4. Aurora’s Lakeside Charm

Nestled on Cayuga Lake’s eastern shore, Aurora feels like stepping into a storybook village. Historic buildings house quaint shops while the prestigious Wells College campus adds architectural splendor to this tiny hamlet.

The crown jewel is the Inns of Aurora, a collection of meticulously restored historic properties offering luxurious accommodations with spectacular lake views. Local dining shines at places like Aurora Inn Dining Room, where farm-to-table cuisine celebrates regional flavors.

Don’t miss a sunset stroll along the waterfront or a visit to MacKenzie-Childs, the whimsical home furnishings company headquartered in a Victorian farmhouse just outside town.

5. Trumansburg’s Musical Soul

Just a stone’s throw from Ithaca but worlds away in pace, Trumansburg punches above its weight in musical heritage. This unassuming village hosts the Finger Lakes GrassRoots Festival, drawing thousands each July for four days of global music traditions.

The Rongovian Embassy, recently revived after closing, has hosted legendary musicians for decades in a venue that embodies the town’s free-spirited character. Between musical adventures, explore Taughannock Falls State Park, home to the Northeast’s tallest single-drop waterfall at 215 feet – higher than Niagara!

Main Street offers surprises like the Gimme! Coffee roastery and the Hazelnut Kitchen, where farm-to-table dining reaches artistic heights. Before leaving, visit Good To Go for breakfast burritos that locals claim are life-changing.

6. Hammondsport’s Wine Country Haven

At the southern tip of Keuka Lake sits Hammondsport, a village that punches well above its weight in wine history and charm. As the birthplace of American champagne, this tiny community houses the Pleasant Valley Wine Company, the region’s first bonded winery established in 1860.

The village square feels frozen in time, surrounded by Victorian buildings housing craft shops, bakeries, and tasting rooms. Aviation enthusiasts will appreciate the Glenn H. Curtiss Museum, celebrating the local pioneer who once held the title of ‘fastest man on earth.’

After wine tasting, cool off with a swim at Champlin Beach or enjoy waterfront dining at the Waterfront Restaurant with stunning Keuka Lake views.

7. Geneva’s Architectural Treasures

Commanding Seneca Lake’s northern shore, Geneva blends small-town warmth with surprising sophistication. Hobart and William Smith Colleges infuse youthful energy into this historic community, while magnificent 19th-century mansions line South Main Street in what locals call the ‘South Main Street Historic District.’

The Smith Opera House, an 1894 theater restored to its original glory, hosts films and performances year-round. For culinary adventures, FLX Table offers one of the region’s most sought-after dining experiences – a single communal table serving farm-fresh cuisine.

Geneva’s renaissance continues with Linden Street’s transformation into a pedestrian-friendly district of restaurants and shops. Visit Pulteney Park, the town’s original center, where a historic trip-hammer commemorates the blacksmithing industry that helped build this lakeside gem.

8. Watkins Glen’s Gorge-ous Wonders

Famous for its NASCAR racetrack, Watkins Glen offers natural thrills that rival any motorsport. The showstopping Watkins Glen State Park features a two-mile gorge trail where hikers pass 19 waterfalls while ascending 832 stone steps through breathtaking rock formations carved over 12,000 years.

Downtown has evolved beyond typical tourist trappings with establishments like Rooster Fish Brewing, the Finger Lakes’ first farm brewery. Franklin Street’s shops offer everything from local arts to international treasures. For an unforgettable meal, try Graft wine + cider bar, where Finger Lakes ingredients shine in creative small plates.

Captain Bill’s scenic boat tours provide a different perspective on Seneca Lake’s beauty, while the Schooner True Love offers romantic sunset sails on a vessel featured in the classic film ‘High Society.’

9. Canandaigua’s Victorian Splendor

Nicknamed ‘The Chosen Spot,’ Canandaigua combines small-city amenities with small-town charm at its namesake lake’s northern tip. The breathtaking Sonnenberg Gardens & Mansion State Historic Park showcases a 40-room Queen Anne mansion surrounded by nine formal gardens, transporting visitors to the Gilded Age.

The New York Wine & Culinary Center (now New York Kitchen) offers hands-on cooking classes focusing on regional ingredients. Downtown’s historic district features beautifully preserved 19th-century architecture housing independent shops and restaurants.

Roseland Waterpark provides family fun on hot summer days, while the Canandaigua Lady, a replica 19th-century paddlewheel boat, offers leisurely lake cruises. Winter brings cross-country skiing at nearby Bristol Mountain and the magical Christkindl Market, celebrating the area’s German heritage.

10. Owego’s Riverfront Nostalgia

Technically outside the Finger Lakes but worthy of inclusion, Owego sits on the Susquehanna River with one of New York’s most charming historic districts. The village’s name comes from the Iroquois word ‘ahwaga,’ meaning ‘where the valley widens.’

Front Street’s brick facades house treasures like the Hand of Man Museum, displaying an eclectic private collection, and the Riverow Bookshop, occupying four connected 19th-century buildings. The Belva Lockwood Inn, named for the first woman to run for president, offers elegant accommodations in a restored Victorian home.

Summer brings the Strawberry Festival, attracting 30,000 visitors annually. For spectacular views, drive up to Hiawatha Island Overlook or climb the 120-year-old Evergreen Cemetery hillside for panoramic vistas of the river valley.

11. Seneca Falls’ Feminist History

Walking through Seneca Falls feels like stepping into a living history book of women’s rights. This canal town hosted the first Women’s Rights Convention in 1848, launching the American women’s suffrage movement. The Women’s Rights National Historical Park preserves this legacy, including the Wesleyan Chapel where the convention was held.

Film buffs might recognize elements of the town as inspiration for Bedford Falls in ‘It’s a Wonderful Life.’ The It’s a Wonderful Life Museum celebrates this connection year-round, while the annual festival transforms the town each December.

Cayuga Lake State Park offers swimming and camping, while the Seneca Falls Heritage Area Visitor Center provides canal-side walking paths. For a unique dining experience, try the Café XIX (named for the 19th Amendment) serving locally-sourced fare in a historic setting.