Lexington’s Fall Bucket List

There are always a ton of events and activities in Lexington, but these are the things that are essential to making the most out of your fall season.

the lexington skyline

Downtown Lex on a crisp fall morning | Photo by LEXtoday

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Yesterday, Thurs., Sept. 22, was the first day of fall. I know, right? Where did the summer go?

To ensure you make the most out of Lexington’s foliage festivities, we’ve compiled a Bluegrass bucket list for fall.


If you’re looking to leaf the city behind + explore the countryside — check out this fall foliage map. It predicts when each section of the Commonwealth will experience peak fall foliage.

Additionally, use this list of the top 10 hikes in the Lexington area to plan out your leaf-peeking expedition.

Don’t forget about the yellow tree tunnel on Catalpa Road.


From corn mazes to apple cannons, there are several surrounding farms that host family-friendly activities throughout the fall season.

an aerial of a farm

Lexington’s surrounding farms a full of seasonal, family-friendly activities. | Photo courtesy of Bi-Water Farm


Sip on an Oktoberfest beer or munch on a fried apple dumpling at one of these fall festivals.

  • Country Boy Oktoberfest | Sat., Sept. 24 | 10 a.m.-11 p.m. | Georgetown Taproom, 101 Innovation Way, Georgetown | Free, price of purchase | Sip on locally-brewed Oktoberfest beer, participate in a stein holding contest + listen to live accordion rock music.
  • Michler’s Oktoberfest | Wed., Sept. 28-Fri., Sept. 30 | 4-10 p.m. | Michler’s, 417 E Maxwell St. | Free, price of purchase | Oktoberfest in the garden with live music, giant pretzels, and extra beer taps.
  • Fall Festival | Fri., Oct. 14 + Sat., Oct. 15 | 4-11 p.m. | Mary Queen of the Holy Rosary, 601 Hill N Dale Rd. | Free, price of purchase | The Southland neighborhood festival features food, inflatables, casino games + BINGO.
people at a festival

The stein holding competition is a tradition at Country Boy Brewing’s Oktoberfest festival. | Photo courtesy of Country Boy Brewing

Food + drink

Local coffee shops + breweries have all released fall drink items for the season. Make time to sample a few. Crank & Boom Craft Ice Cream also just released five new seasonal fall flavors.