Discover the ultimate Upstate New York autumn getaway! From the historic Chautauqua Institution and craft breweries to grape harvesting and the famous Wayne County Apple Tasting Tour, here is how to plan a perfect fall New York vacation.
I was born and raised in Rochester, NY, home of Kodak, the world’s largest lilac collection, and Susan B. Anthony. Even though I no longer live there, I still take the opportunity to travel home to visit family and the beautiful surrounding area as much as I can. Here’s how I took the perfect fall vacation in New York State.
Southern Tier New York State: Chautauqua Institution in the Fall
In honor of my sister’s 50th birthday, we made the trip to New York State in October, combining our trip to Rochester, NY with a visit to the world-renowned Chautauqua Institution.
Chautauqua is, in their words:
A community of artists, educators, thinkers, faith leaders and friends dedicated to exploring the best in humanity.
It’s also a truly spectacular place to visit in the fall. Our trip was mid-October, and the absolute perfect time to see the fall leaves in all their glory. Despite the fact that most of the homes are closed up for the winter, sporting huge awnings to protect them from the harsh winters, the grounds are a sight to behold. Their bookstore is still open in October, and I spent much too much time looking at all the unique and clever gifts, spending too much money as well!
Operating continually since it was completed in 1881, the Victorian Athenaeum Hotel is located on the grounds of the institution facing the beautiful Chautauqua Lake. A Road Scholar group was meeting in the hotel during our visit, so we kept our poking around confined to the lobby and the surrounding conference rooms.
I can picture people from the Victorian Age gathered on the expansive front porch discussing things of great importance like politics, philosophy, literature, and travel. While there, take a look at the interior lighting, as some of the early wiring of the hotel was completed by Thomas Edison.
Things to Do In The Chautauqua, New York Area
There are plenty of things to do in the Chautauqua, New York area, even in the fall when most of the Institution is closed. Walk around the historic grounds and look at the restored homes, take in the lake, the landscaping, the fall leaves and the general vibe of the place. Imagine the Victorians discussing intellectual ideas here, just as they do today.
Beyond the gates of the Institution, the Chautauqua region is bursting with autumn flavor and outdoor activities. After a chilly morning of exploring, we traveled just a few miles down the road to the well-known Southern Tier Brewing Company in Lakewood. Famous for their iconic Pumking ale, one of the pioneers of the craft pumpkin beer craze, the brewery is a fantastic fall hangout. I opted for one of their rich, dark stouts, which was the perfect warmer for a brisk October afternoon.
If you love wine history, a stop at Johnson Estate Winery is mandatory. As the oldest estate winery in New York State, they have been producing award-winning wines in the Lake Erie region since three generations of the Johnson family opened it. Sampling their crisp, cool-climate whites while looking out over vineyards heavy with the final harvest of the season is the quintessential New York fall experience.
Pair your wine tasting with a hike on one of the nearby local nature trails to crunch through the fallen leaves and soak in the canopy of autumn colors.
After wrapping up our time in the Southern Tier, I headed back toward my hometown of Rochester to meet up with my sister.
Pro Tip: If you are using Rochester as your home base for an autumn getaway, make sure to check out my ultimate guide to spending the perfect 24 hours in Rochester, NY, featuring canal-side kayaking and the historic Public Market!
From Rochester, we ventured just a bit east for the annual Wayne County New York Apple Tasting Tour. This region sits right on the southern shore of Lake Ontario, creating a unique microclimate that produces some of the best-tasting apples in the country. The official tour features eleven fantastic stops, complete with an app and a passport challenge to earn prizes.
Grape Harvest Festival
One of the absolute highlights of our trip was volunteering for the Young Sommer Winery annual grape harvest. I had never experienced the hands-on magic of clipping ripe grapes straight from the vine. The air was thick with the sweet, rich scent of fermenting fruit. In exchange for a few hours of volunteer field work, the winery treated us like family, providing pastries, hot coffee, and midday snacks, followed by a beautiful, hearty dinner paired seamlessly with their own estate wines. Check out their website for details on this event.
The Wayne County, New York Apple Cider Trail
The apple trail takes you along the shores of Lake Ontario, winding through some of the most beautiful apple orchards in the country. We sampled fried cakes (don’t you dare call them donuts), cider, apples, and of course, hard cider from the various apple orchards along the trail. There are eleven stops in total. The tour has an official app and passport, which you can download from their website, along with tips and prizes for completing their challenges.
The rest of the trail winds through rolling hills draped in autumn gold, leading you to incredible farm stands and orchards. We spent the weekend sampling fresh-pressed apple cider, crisp Honeycrisps, and local hard ciders.
And, of course, we indulged in plenty of fried cakes. Being from Rochester, let me clarify: don’t you dare call them donuts! Upstate New York cider fried cakes are an art form—crispy on the outside, perfectly dense on the inside, and best enjoyed warm while watching the autumn leaves fall.
More New York Travel Tips
If you like this leaf-peeping vacation, check out similar trip ideas perfect for a long weekend in Louisville, KY, the Finger Lakes, NY, a week in Torch Lake, MI, and more.
No autumn trip to Upstate New York is complete without checking out the local cider mills and canal towns. For a great urban-meets-nature itinerary that includes fresh cider donuts, check out my guide to spending 24 hours in Rochester, NY.
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