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| Day, Date - Event |
| Friday, September 1st - Old Kentucky Home Bicycle Tour |
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| Friday, September 1st - “A House Divided”, September 1-30 |
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| Saturday, September 2nd - Old Kentucky Home Bicycle Tour |
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| Saturday, September 2nd - Kentucky Railway Museum’s Dining on the Rails |
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| Saturday, September 2nd - Bardstown Ghost Trek |
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| Sunday, September 3rd - Old Kentucky Home Bicycle Tour |
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| Friday, September 8th - Live at the Park Concert Series, Draw the Line – A Tribute to Aerosmith |
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| Friday, September 8th - A House Divided”, September 8-30 |
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| Saturday, September 9th - Rolling Fork Iron Horse Festival |
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| Saturday, September 9th - My Old Kentucky Dinner Train’s Bourbon Excursion |
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| Saturday, September 9th - Bardstown Ghost Trek |
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| Monday, September 11th - Kentucky Bourbon Festival |
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| Tuesday, September 12th - Kentucky Bourbon Festival |
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| Wednesday, September 13th - “Half Pint of Whiskey Trivia with a Shot of Humor” |
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| Wednesday, September 13th - Kentucky Bourbon Festival |
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| Thursday, September 14th - Kentucky Bourbon Festival |
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| Thursday, September 14th - Kentucky Bourbon Festival |
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| Friday, September 15th - A House Divided”, September 15-30 |
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| Friday, September 15th - Kentucky Bourbon Festival |
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| Saturday, September 16th - Kentucky Railway Museum’s Train Robbery |
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| Saturday, September 16th - Kentucky Bourbon Festival |
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| Saturday, September 16th - Kentucky Railway Museum’s Murder Mystery Theatre |
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| Saturday, September 16th - Bernheim Forest’s BugFest |
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| Saturday, September 16th - Bardstown Ghost Trek |
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| Sunday, September 17th - Guthrie Opportunity Center's Bourbon Brunch |
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| Sunday, September 17th - Kentucky Railway Museum’s Train Robbery |
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| Sunday, September 17th - Kentucky Bourbon Festival |
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| Tuesday, September 19th - Wickland Board Meeting |
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| Thursday, September 21st - Barton 1792 Distillery Sundown Series |
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| Friday, September 22nd - A House Divided”, September 22-30 |
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| Saturday, September 23rd - Whiskey City Cruisers |
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| Saturday, September 23rd - Kentucky Railway Museum’s Pumpkin Patch Express |
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| Saturday, September 23rd - My Old Kentucky Dinner Train's Murder Mystery |
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| Saturday, September 23rd - Bardstown Ghost Trek |
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| Sunday, September 24th - Kentucky Railway Museum’s Pumpkin Patch Express |
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| Saturday, September 30th - Bardstown Ghost Trek |
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