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| Day, Date - Event |
| Friday, May 3rd - A Visit with the Spirits of Wickland |
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| Friday, May 3rd - The Bardstown Opry |
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| Sunday, May 5th - Old Fashioned Family Barbeque |
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| Friday, May 10th - A Visit with the Spirits of Wickland |
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| Friday, May 10th - My Old Kentucky Dinner Train's Bourbon Excursion |
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| Friday, May 10th - The Bardstown Opry |
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| Saturday, May 11th - Whiskey City Cruisers |
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| Saturday, May 11th - Kentucky Railway Museum’s Girl Scout Day |
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| Friday, May 17th - Springhill Winery’s Kick Back Friday Dinner |
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| Friday, May 17th - Third on Third |
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| Friday, May 17th - Wickland Community Yard Sale |
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| Friday, May 17th - A Visit with the Spirits of Wickland |
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| Friday, May 17th - Bourbon Open Golf Tournament |
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| Friday, May 17th - The Bardstown Opry |
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| Saturday, May 18th - Third on Third |
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| Saturday, May 18th - Bardstown Home Guard 7th KY and 24th KY |
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| Saturday, May 18th - Wickland Community Yard Sale |
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| Saturday, May 18th - Bernheim's BloomFest & Spring Plant Sale |
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| Saturday, May 18th - Bourbon Open Golf Tournament |
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| Sunday, May 19th - Bardstown Home Guard 7th KY and 24th KY |
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| Sunday, May 19th - Bourbon Open Golf Tournament |
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| Tuesday, May 21st - Friends of Wickland Meeting |
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| Tuesday, May 21st - Tourism Board Meeting |
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| Friday, May 24th - Summer Band Concerts |
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| Friday, May 24th - The Bardstown Opry |
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| Friday, May 24th - A Visit with the Spirits of Wickland |
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| Saturday, May 25th - My Old Kentucky Dinner Train's Murder Mystery |
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| Saturday, May 25th - Kentucky Railway Museum’s Murder Mystery Theatre |
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| Friday, May 31st - A Visit with the Spirits of Wickland |
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| Friday, May 31st - Summer Band Concerts |
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| Friday, May 31st - The Bardstown Opry |
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