Main Street in downtown Canandaigua, New York. Editorial credit: Ritu Manoj Jethani / Shutterstock.com.

6 Friendliest Towns to Visit in the Finger Lakes

The friendliest towns in the Finger Lakes show it in how they run, not in how they advertise. In Skaneateles, a boat still hand-delivers mail to dockside boxes every summer morning. Geneva closes Linden Street to cars on summer Fridays for music and outdoor dining. Penn Yan runs a farmers market on Main Street through the season. The six towns here share the same setup: a Finger Lake, a walkable Main Street, and a calendar built on local turnout. The welcome holds in peak season and in the quiet weeks.

Skaneateles

Pier and boats docked in the Skaneateles Lake, one of the Finger Lakes
Pier and boats docked in the Skaneateles Lake, one of the Finger Lakes, via PQK / Shutterstock.com

Skaneateles still sends a boat out to hand-deliver mail to dockside boxes every summer morning. Mid-Lakes Navigation runs the route out of the village pier on a three-hour loop, the way smaller boats have since the early 1900s. Skaneateles wraps the northern tip of Skaneateles Lake, one of the cleanest lakes in the country. The lake supplies unfiltered drinking water to the Syracuse area and serves about 220,000 people. It is one of only a handful of unfiltered public water supplies in the United States. The 16-mile lake has drawn summer families since the late 1800s. William Henry Seward, Lincoln's Secretary of State, is said to have called it the most beautiful body of water in the world.

The calendar keeps people together through the year. The Skaneateles Music Festival fills August with chamber concerts in barns and lakeside venues. December brings the Dickens Christmas Festival, when costumed characters walk the streets every weekend. Anyela's Vineyards runs tastings on a hillside south of the village. The Skaneateles Historical Society Museum at the Creamery tells the village's boat-building story.

Penn Yan

Keuka Lake in Penn Yan, New York
Keuka Lake in Penn Yan, New York. Editorial credit: PQK / Shutterstock.com.

Penn Yan fills Main Street with a farmers market every week from June through October, and the regulars there greet a newcomer first. The Keuka Arts Festival lands in June, and the Yates County Fair packs the grounds in July. The village holds the northeastern tip of Keuka Lake, the only Finger Lake shaped like a Y, where the eastern and western branches meet and run south as a third arm. The name Penn Yan blends Pennsylvania and Yankee. It was a compromise from the early 1800s, when settlers from both directions could not agree on a name. The town has been bringing different people together ever since.

The wineries keep the same easy pace. Fox Run Vineyards and Dr. Konstantin Frank Winery both run tastings within a 20-minute drive. The Outlet Trail follows an old rail bed about seven miles between Penn Yan and Dresden. Mills, waterfalls, and quiet ruins line the route along the Keuka Lake outlet.

Geneva

Vibrant buildings along the main street of Geneva, New York
Vibrant buildings along the main street of Geneva, New York. Editorial credit: Spiroview Inc / Shutterstock.com

On Friday nights, Geneva closes Linden Street to cars and turns the block over to live music, outdoor dining, and neighbors who stay late. Geneva has run as a college town since Hobart College opened here in 1822. William Smith College joined in 1908 to form Hobart and William Smith Colleges. The students keep the streets busy year-round. Seneca Lake State Park runs along the water with boat launches, a swim beach, and the Sprayground splash-pad that draws families all summer.

The landmarks carry the same open feeling. Rose Hill Mansion runs daily tours through an 1839 Greek Revival house. William Kerley Strong built it, and the estate took its name from an earlier owner, Robert Selden Rose. The Smith Opera House opened on Seneca Street in 1894 and still books touring acts, comedy nights, and classic films in a 1,400-seat house. The Geneva Music Festival fills churches and the opera house with chamber programming each June.

Watkins Glen

Pier on Seneca Lake in Watkins Glen, New York.
Pier on Seneca Lake in Watkins Glen, New York.

Watkins Glen takes in tens of thousands of race fans on a single weekend, and the lakefront village keeps its easygoing pace anyway. It anchors the southern end of Seneca Lake. East of downtown, Watkins Glen International hosts the NASCAR Cup Series each year, plus the IMSA Sahlen's Six Hours of the Glen in June. The International Motor Racing Research Center on Franklin Street holds a research library and rotating motorsports exhibits.

West of downtown, Watkins Glen State Park cuts two miles into a glacier-carved gorge past 19 waterfalls. The Gorge Trail runs alongside, behind, and over the falls on stone steps cut into the rock. The Seneca Lake Wine Trail loops more than 30 wineries around the lake, with Lakewood Vineyards, Glenora Wine Cellars, and Castel Grisch close to town. The Finger Lakes Wine Festival fills a July weekend at the racetrack with producers from across the region.

Hammondsport

Aerial view of Hammondsport, New York.
Aerial view of Hammondsport, New York. Image credit: Ak1047 via Wikimedia Commons.

Hammondsport draws the whole village to a Civil War-era bandstand on the green for summer concerts. Pulteney Square anchors downtown around it. The Hammondsport Festival of Crafts brings juried artisans to the green each August. The village holds the southern end of Keuka Lake and runs as the heart of New York wine country. Pleasant Valley Wine Company opened just outside town in 1860, the oldest winery in the Finger Lakes and U.S. Bonded Winery No. 1. Heron Hill Winery pours up on the bluff with a tasting room over the lake.

The village also raised an aviation pioneer. Glenn H. Curtiss was born here in 1878, held U.S. Pilot's License No. 1, and ranks as a founder of the American aircraft industry. The Glenn H. Curtiss Museum on State Route 54 fills a 60,000-square-foot former winery building with more than 20 historic aircraft, vintage motorcycles, and early automobiles. A working shop lets volunteers rebuild historic planes in front of anyone who stops in.

Canandaigua

Main Street in downtown Canandaigua, New York
Main Street in downtown Canandaigua, New York. Editorial credit: Ritu Manoj Jethani / Shutterstock.com

Most evenings, Canandaigua's wide Main Street runs down to a city pier where the whole town gathers once the boat traffic settles. The name Canandaigua comes from the Seneca word for "the chosen spot," and the choice holds up. The village holds the northern tip of Canandaigua Lake. Sonnenberg Gardens & Mansion State Historic Park covers 50 acres of themed gardens around a 40-room Queen Anne mansion. The New York City financier Frederick Ferris Thompson and his wife Mary Clark Thompson built it in 1887. The estate's 1906 Japanese garden counts as the first privately owned Japanese garden in the country.

The town keeps its history close and open to anyone. The Canandaigua Wine Trail loops the lake with stops at Casa Larga Vineyards, Heron Hill, and Inspire Moore Winery. Granger Homestead and Carriage Museum runs tours through a Federal-style mansion built in 1816 for Gideon Granger, postmaster general under Jefferson and Madison. The Canandaigua Art & Music Festival fills Main Street with juried artists and live music each July.

What Friendly Looks Like Here

The welcome in these towns runs on routine more than on any single attraction. Skaneateles sends out the mailboat. Geneva closes Linden Street on Fridays. Hammondsport fills the bandstand on the green. Penn Yan greets the market crowd, Watkins Glen hosts the race weekends, and Canandaigua gathers at the pier. Pick any one as a base for a weekend in your own state, and the lake out the window does the rest. A first visit tends to turn into a standing one.

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