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Shawnee Hills
Wine Trail Events

Live music, seasonal pairings, festivals and more—plan your visit around these dates.
ALL Class/Workshop Festival Food & Pairings Live Music
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Upcoming Events

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

Winemaker Dinner Series

Join us in 2026 for our Winemaker Dinner Series. Meet the people behind your favorite wines and learn about the winemaking process from grape to glass. Enjoy an unforgettable experience combining exceptional wines and an exquisite menu. Shawnee Hills Wine Trail: Winemaker Dinner Series April 24, 2026 – Feather Hills Vineyard (Hwy 51 Location) Reception […]
April 24, 2026
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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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#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.
Download the map

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