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Showing events for April 2026

ALL Class/Workshop Festival Food & Pairings Live Music

Event2

Settle into an evening among the vines with cozy fire pits, seasonal small plates, and an intimate acoustic performance. Our tasting bar will feature limited fall releases by the glass and bottle, with suggested pairings to match the music and mood. Seating is first-come, with a limited number of reserved tables available. Dress for the […]
October 30, 2025
event details

Event2

Settle into an evening among the vines with cozy fire pits, seasonal small plates, and...

October 30, 2025
EVENT DETAILS
Happening Here

Upcoming Events

Live music, seasonal pairings, and special tastings hosted at wineries along the route.

Derby Day

The 151st Kentucky Derby is almost here, and there’s no better place to watch the Run for the Roses than Blue Sky Vineyard, glass of Illinois wine in hand, surrounded by our signature Tuscan atmosphere.
May 2, 2026
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Anniversary Celebration

Wine, music & spring cheer.
May 2, 2026
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Event 2

Relax, sip & enjoy the trail.
September 19, 2026
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HalloWine

Our biggest event of the year!
October 30, 2026
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Event 2

Relax, sip & enjoy the trail.
October 24, 2026
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Slushy Sunday

Relax, sip & enjoy the trail.
October 24, 2026
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Halloween Event

Sip, dance & celebrate in spooky style.
October 31, 2026
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Harry Potter Day

Dress up, drink up, and cast spells.
September 6, 2026
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Grape Stomp

Summer grape-stomping fun.
June 6, 2026
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Event2

Settle into an evening among the vines with cozy fire pits, seasonal small plates, and...

October 30, 2025
EVENT DETAILS

#ShawneeHillsWineTrail

Let’s plan your trip...
We’ve created a map to help guide you through the Shawnee Hills Wine Trail so that you can spend more time sipping and relaxing and less time sweating the details of your trip.
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