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Jessamine County Events for 5/30/2025 to 6/1/2025
Arts And Entertainment

Front Porch Pickin'

Friday, May 30, 2025 from 6:00pm to 9:00pm
Wildside Winery and Vineyard
Wildside Winery
Versailles, KY
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Lexington Chamber Orchestra

Friday, May 30, 2025 at 7:30pm
Lexington Opera House
Lexington, KY
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Lexington Chamber Orchestra

Railbird Festival

Saturday, May 31, 2025
The Infield at Red Mile
Lexington, KY
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Railbird Festival

Live Music: Downing Street

Saturday, May 31, 2025 from 1:00pm to 4:00pm
Wildside Winery and Vineyard
Wildside Winery
Versailles, KY
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Live Music - Kevin Cruise

Saturday, May 31, 2025 from 4:00pm to 7:00pm
Talon Winery
Lexington, KY
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Cold with September Mourning / University Drive

Saturday, May 31, 2025 at 7:00pm
Manchester Music Hall
Lexington, KY
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Cold with September Mourning / University Drive

Lexington Peddlers Mall Summer Fest

Sunday, Jun 1, 2025 from 11:00am to 6:00pm
Lexington Peddlers Mall Summer Fest
Lexington Peddler's Mall
Lexington, KY
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Lexington Peddlers Mall Summer Fest

Railbird Festival

Sunday, Jun 1, 2025 at 1:00pm
Railbird Festival
The Infield at Red Mile
Lexington, KY
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Railbird Festival
Upcoming Jessamine County Events This Weekend Next Weekend
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