This Quaint New York Finger Lakes Town Offers A Charming Downtown & Scenic Apple Orchards

New York has always been a magnet for travelers, not only for the skyscrapers of Manhattan but also for its striking natural beauty. Among its most treasured landscapes are the Finger Lakes, a chain of eleven glacier-carved waters stretching like ribbons across upstate New York. At the heart of this region lies Penn Yan, one of the most picturesque towns to visit on the east coast. With a population of just 5026, it offers a breath of fresh air and a vibe that feels worlds apart from the bustle of the city. Penn Yan has nearly 200-year-old buildings lining the streets, each reflecting a distinct style from 19th-and-20th-century American architecture. Walking through downtown feels like stepping into one of those charming towns from a history book that invites you in at every turn.

This quaint town sits in Yates County, on the northeastern shore of the eastern branch of Keuka Lake, the third largest of the Finger Lakes. This setting alone can make anyone fall in love with the town, but its history adds even more character. Originally known as Union, the name never resonated with residents.

Settlers from Pennsylvania and New England (Yankees) came up with a compromise: "Penn" from Pennsylvania and "Yan" from Yankee, creating the name Penn Yan. This town was incorporated in 1833, the same year Crooked Lake Canal opened and sparked economic growth. The arrival of the railroad in 1850 transformed Penn Yan into a hub for agriculture, especially grape-growing, which naturally paved the way for the orchards and vineyards that define the area today.

For outdoor lovers, the trails are where the fun begins. The 5.2-mile Seneca Mill and Cascade Mill Falls Trail and the 1.5-mile Keuka Lake Yellow and Blue Trail Loop are both popular and easy to navigate, but the highlight is the 13.5-mile Keuka Lake Outlet Trail, which runs between Keuka and Seneca Lakes. Along the way, you'll pass waterfalls, find benches for breaks, and take in sweeping lake views. You may sweat a little on the path, but the scenery makes every step worth it. And the trail isn't just for walking — you can fish, bike, ride horseback, or even snowmobile, depending on the season.

The Yates County History Center is the perfect stop for history buffs. The Oliver House Museum, with more than 50,000 artifacts, takes you back to the 18th-century, while the second floor keeps kids engaged with games and playful farm scenes. Admission ranges from $10 to $15, and the museum is open Tuesday through Friday. The History Center also includes the L. Caroline Underwood Museum, the Spencer Research Center, the Bullock Imaging Center, and the Scherer Carriage House, all working together to show how much of the town's past has been carefully preserved.

From April through November, Saturdays bring the Windmill Farm and Craft Market to life with over 175 vendors selling local produce, crafts, and baked goods. And of course, no trip to the Finger Lakes is complete without wine. Penn Yan is one of the best wine-tasting vacation destination options in the region, with popular vineyards like Fox Run, Keuka Spring, and Red Tail Ridge. For a more seamless experience, the Keuka Lake Wine Tour covers four wineries with transport and lunch included for $256.32.

Just when you think you've experienced everything Penn Yan has to offer, the best part is still waiting: apple-picking. The Apple Barrel Orchards is the go-to spot for u-pick experiences, with harvest season running from September through October. Here you'll find everything from sweet cherries and Concord grapes to Gala, Cortland, and Fuji apples. Once you've filled your container, you'll check out at the farm stand where prices are fair. To keep the orchards thriving, visitors are asked to stay in designated areas, avoid climbing trees, and leave no litter behind.

Frederick Douglass Greater Rochester International Airport is the closest option for international arrivals. From there, it's a one-hour-and- 30-minute bus ride to Penn Yan. You can also fly into Buffalo Niagara International Airport, which is just over two hours away by bus. Both trips range from $21 to $60. If you prefer a longer but more scenic journey, the Port Authority Bus Terminal in New York City offers a five-hour-and-55-minute scenic ride to Yates County, with tickets ranging from $45 to $179. Once you arrive in Penn Yan, there are plenty of affordable places to stay without stretching your budget. Options like Hampton Inn, Best Western Plus Vineyard Inn and Suites, and Microtel Inn and Suites by Wyndham cost between $77- $84 per night.

And if you're still wondering when and how to plan the perfect holiday trip in New York, Penn Yan's charm lasts all year. Summer brings warm weather and lake adventures, fall is harvest season with orchards in full swing, winter transforms the area into a hub for snow-sports, and spring is filled with blossoms and fresh air. No matter when you decide to go, Penn Yan offers an experience that feels personal and memorable.