There are many reasons to love September and October in Kentucky, and one of them is the wide variety of activities that are perfect for a lovely autumn day. During these few short months of cooler temperatures and vibrant color, we want to be outside, soaking it in before winter creeps into the Bluegrass State. If you’re looking to explore our beautiful state this season, check out our list of picture-perfect fall day trips to take throughout Kentucky.

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If only we could fit in all of these fun excursions in one short season — the weeks in September and October in Kentucky fill up fast! Luckily, there’s always next year, too. How many of these fall day trips have you taken? Do you have another favorite spot in Kentucky to explore during fall? Share your thoughts with us in the comments!

Wondering when fall foliage will peak in your next of the woods? Kentucky in October is generally prime fall foliage season, and you can learn more about what and when to expect the best leaf peeping conditions in this article.

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October in Kentucky

What are some fun festivals that happen in September and October in Kentucky?

There's nothing like fall festival season in Kentucky, and there are definitely some perennial favorites we eagerly await each year! There are the tried-and-true festivals that scream "fall," complete with pumpkins galore, hayrides, apple cider, and spooky fun, but we're partial to the quirky, only-in-Kentucky fall festivals that are truly unique to the Bluegrass State.

For example, each September, the World Chicken Festival fills the streets of Corbin, Kentucky, with hundreds of Colonel Sanders lookalikes and the delicious, unmistakable, and wholly irresistible aroma of fried chicken. The festival is home to numerous only-in-Kentucky spectacles, from the World’s Largest Stainless Steel Skillet, to culinary cook-offs *in* the aforementioned superlative skillet, to a Colonel Harland Sanders Look-a-Like Contest that will have you seeing double! If you've never been, definitely put this festival on your fall bucket list.

In October, the woolly worm takes front-and-center in the small Kentucky town of Beattyville, during the aptly-named Woolly Worm Festival. Far from your typical pumpkins-and-hayrides fall fete, the Woolly Worm Festival is a beloved tradition rooted in Lee County’s culture. And, in fact, there's a very logical explanation for this fuzzy festival. You see, the woolly worm is believed to forecast the weather for the coming winter season. A woolly worm’s body has 13 segments -- each corresponding to a week in winter. If a segment is light brown, that means the week will be mild. If a segment is black, that means a harsh, cold week. The worm acted as a weather predictor for many old time farmers who would harvest crop and cut firewood in preparation for the upcoming winter; and, in fact, there are many "Woolly Worm" festivals held throughout the U.S. each fall! But Kentucky's is the best.

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