Best Things To Do In Penn Yan, NY

Experience America’s Most Fun Small Town when you explore Penn Yan in the Finger Lakes region. From seaplane rides to hiking to wine tasting, there’s never a shortage of things to do in Penn Yan, NY! But, if you do decide to venture away from this fun-filled town for a little bit (since it’s close to places like Canandaigua or Watkins Glen), make sure to take a look at our website. It includes local favorites when it comes to the best restaurants, attractions, outdoor adventures, and wine trails along the lakes.

Things to Do in Penn Yan, NY

History, Art, and Culture in Penn Yan

The Windmill Farm & Craft Market

We love spending time at a farmers market, and The Windmill Farm & Craft Market is one of our favorites! It’s the oldest of its kind in Upstate New York and runs from the last Saturday in April until the second Saturday in December. That means it’s also one of the longest-running markets in terms of its open season as well! The produce here is the highlight of the market, as well as the vendors selling prepared foods, souvenirs, and flowers. Get some holiday shopping complete when you visit the Windmill. Make a day of it by enjoying a delicious lunch at one of the many food vendors.

Keuka Lake Wine Trail

Enjoy world-class wineries, fun events, and plenty of gorgeous scenic views when you explore the Keuka Lake Wine Trail! The smallest of the trails in the Finger Lakes Wine Region, this route features six outstanding family-owned wineries. Learn about the processes of harvest season and the importance of the Finger Lakes region on the entire wine industry.

Outdoor Recreation in Penn Yan

Keuka Outlet Trail

Looking for a little bit of fresh air and sunshine? You can explore 7 miles of natural trails and take in the beautiful waterfalls found along the Keuka Outlet Trail. The trail head starts at our hotel so parking will never be an issue even on the most busy days. Walk the dog on their gorgeous hiking trail, visit the quaint town of Dresden, or try x-country skiing in the winter months!

Finger Lakes Rail Riders

Bring your family and friends to a relaxing, breezy ride along the tracks of Yates County!
Enjoy the experience of rail biking at any age and with any ability! You don’t have to be an athlete to ride a rail bike. If you need a break from pedaling, everyone has a freewheel and can coast.

From your bike, you will experience working farms and see picturesque scenery. See relics that remain from the railroad communications. There is even a one-room Mennonite schoolhouse along our rail. Take this opportunity to show your family where their food comes from.

Food and Wine in Penn Yan

Downtown Business District

Explore downtown Penn Yan, New York, and visit the Business district. This delightful area has some of the best small businesses, Instagrammable streetscapes, restaurants, and boutiques.

Unwind after a day of exploring the charming town of Penn Yan in one of our six suites. We offer gorgeous suites in New York that allow you to be close to the best outdoor recreation, shopping, and historic sites. So, what are you waiting for?  Book Now and start planning your dream getaway today!