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| Day, Date - Event |
| Friday, May 2nd - The Bardstown Opry |
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| Friday, May 2nd - A Visit with the Spirits of Wickland |
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| Friday, May 2nd - Bardstown Community Theatre Presents To Kill A Mockingbird |
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| Sunday, May 4th - Bardstown Community Theatre Presents To Kill A Mockingbird |
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| Friday, May 9th - The Bardstown Opry |
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| Friday, May 9th - A Visit with the Spirits of Wickland |
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| Friday, May 9th - Bardstown Community Theatre Presents To Kill A Mockingbird |
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| Saturday, May 10th - Kentucky Railway Museum’s Girl Scout Day |
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| Saturday, May 10th - Battle of the Bluegrass |
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| Saturday, May 10th - Whiskey City Cruisers |
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| Saturday, May 10th - Bardstown Community Theatre Presents To Kill A Mockingbird |
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| Saturday, May 10th - Kentucky Railway Museum’s Dining on the Rails |
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| Sunday, May 11th - Bardstown Community Theatre Presents To Kill A Mockingbird |
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| Friday, May 16th - Third on Third |
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| Friday, May 16th - Bourbon Open Golf Tournament |
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| Friday, May 16th - A Visit with the Spirits of Wickland |
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| Friday, May 16th - The Bardstown Opry |
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| Saturday, May 17th - Kentucky Railway Museum’s 40’s Weekend |
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| Saturday, May 17th - Old Kentucky Home District Boy Scout Merit Badge Fair |
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| Saturday, May 17th - Third on Third |
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| Saturday, May 17th - Kentucky Railway Museum’s Murder Mystery Theatre |
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| Saturday, May 17th - Bernheim's BloomFest and Spring Plant Sale |
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| Saturday, May 17th - Bourbon Open Golf Tournament |
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| Sunday, May 18th - Kentucky Railway Museum’s 40’s Weekend |
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| Sunday, May 18th - Bourbon Open Golf Tournament |
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| Sunday, May 18th - Old Kentucky Home District Boy Scout Merit Badge Fair |
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| Monday, May 19th - Old Kentucky Home District Boy Scout Merit Badge Fair |
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| Tuesday, May 20th - Tourism Board Meeting |
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| Tuesday, May 20th - Friends of Wickland Meeting |
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| Friday, May 23rd - A Visit with the Spirits of Wickland |
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| Friday, May 23rd - Summer Band Concerts |
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| Friday, May 23rd - The Bardstown Opry |
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| Friday, May 30th - A Visit with the Spirits of Wickland |
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| Friday, May 30th - The Bardstown Opry |
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| Friday, May 30th - Summer Band Concerts |
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| Saturday, May 31st - Wine and Cheese Tasting Festival |
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| Saturday, May 31st - My Old Kentucky Dinner Train's Murder Mystery |
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| Saturday, May 31st - Kentucky Railway Museum’s Train Robbery |
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