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Spice, Sangria & Stage Lights

Some weeks whisper.


This one sizzles.


From laughter under stage lights inside the historic Thoroughbred Theatre to bold chili battles at the winery… from a midweek vineyard reset to sangria drifting through Sunday afternoon — Wildside is alive in all the best ways.


Here’s how the week unfolds.


🧘‍♀️ A Midweek Reset in the Vineyard

Wine Down Wednesday invites you to slow down.

Movement between the vines. Breath under open sky. A glass waiting after class.

Midweek doesn’t have to feel rushed. It can feel intentional.


🎭 Stage Lights & Stand-Up

At Wildside Wine Bar — located inside the historic Thoroughbred Theatre in Midway — Comedy Night brings a different kind of energy.

The room fills. The lights dim. The laughter builds.

There’s something about sharing a joke in an intimate theatre setting that feels electric. Add a glass of wine and suddenly the whole week loosens its grip.

This isn’t just stand-up.It’s shared release.


🌶 The Heat Is On: Wildside Chili Throwdown

Saturday, February 21 | 2:00 PM

We go until the chili runs out.


We’ve heard the rumors.


Everyone in Woodford County “has the best chili.”


Your uncle says his is award-winning.Your neighbor swears hers can bring a grown man to his knees.Your friend’s cousin’s barber once took third place at a county fair in 1998.


Cute.

Bring it.

The Wildside Chili Throwdown is where reputations are made, egos are tested, and someone walks away with bragging rights that last all year.


How It Works:

For $5, guests receive a tasting cup, spoon, and three voting tickets. They taste everything. They choose wisely.


And then we crown:

🥇 Champion of the Cauldron🥈 Spicy But Not Supreme🥉 They Tried and We Respect That


Think your chili can take the heat?

There’s still room to compete.


Bring your slow-simmered secrets.Your heirloom spice blend.Your confidence.

We’ll bring the wine and the crowd.

May flavor favor the bold.


🍷 Slow Sundays, Done Right

Sangria Sunday with James Beers & the Wandering Woodsmen softens the tempo.

Live music. House-made sangria. Conversations that linger.

It’s not rushed. It’s not loud.

It’s the kind of Sunday that reminds you why gathering matters.


🌿 And Then, We Grow

Monday marks the launch of the Wildside Garden Club.

Because Wildside isn’t only about what happens on a stage or in a glass.

It’s about what grows in community.

This week carries spice, sangria, and stage lights.

And it plants something new.

Join us.

 
 
 

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About Wildside Winery
Locally owned and wildly loved, Wildside Winery is a Kentucky destination for wine, community, and creativity. With more than 40 handcrafted wines, year-round festivals, and Wild Woman gatherings, we celebrate living boldly and sipping beautifully.

Visit Us
5500 Troy Pike, Versailles, KY
Mon–Sat 12–7 | Sun 12–5
(859) 879-3982
Family & dog-friendly • Free parking

Outside food & drink not permitted

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