48 Hours in Kentucky: Fall Favorites with Laura Lees Gilbert.

Laura Gilbert
Oct 7
2 min read

Kentucky in the fall? That’s my jam. Leaves are loud, bourbon’s smooth, and the backroads will get you lost in the best way. Here’s how I’d spend 48 hours. Come along, you’ll thank me later.

Day One: Coffee, Lunch, and Shaker Living

Ace Coffee in Cave City because gas-station coffee is a crime.
Bluegrass Tavern in Bardstown is lunch that tastes like home and comes with a side of small-town gossip.
J. Sampson Antiques & Books in Harrodsburg. Period. Walk in for “a look,” walk out with something your grandmother swears she used to own.
Shaker Village! Book dinner and breakfast early or you’ll be staring at other people’s biscuits with envy.
Bring your walking shoes. Shakertown mornings are prettier than half the postcards they sell in gift shops.
Go on a Friday because nothing says Kentucky like a sunset, a live band, and bourbon on the patio.

Day Two: Castles, Antiques & Bowling Shoes

Wake up and pretend you’re the healthy kind with a walk or run. Reward yourself with Shaker breakfast.
Castle & Key— the grounds, the story, the bourbon. She’s a 10.
Irish Acres in Nonesuch— antiques for days and a lunch reservation harder to land than Derby tickets.
Bloomfield — if Nettie Jarvis is open, stop in. If not, snag an Airbnb that looks like it fell out of a Southern Living spread.
Evening at Ernie’s Tavern — eat, bowl, sip bourbon, and pretend you’ve stepped back into 1955.

Day Three: Old Stones, Old Stories, One Last Drink

Is it a Sunday? Start with Mass at St. Joseph’s in Bardstown. Built in 1819. She’s older than half the bourbon barrels in town.
Lunch at Talbott Tavern (where everyone has a story of “that one night”) or keep it cozy at Mimi’s.
On the way home, swing by The Dive in Cave City for a Bloody Mary that’ll make you forget Monday’s coming.