| The Winter Park Playhouse Calendar |
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| ← October | November 2021 | December → |
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| The Swing It! Girls: Salute to Veterans | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Tay Anderson Spotlight Cabaret Series | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Tay Anderson Spotlight Cabaret Series | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Tay Anderson Spotlight Cabaret Series - VIRTUAL | 5:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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| Christmas My Way: A Sinatra Holiday Bash | 2:00 pm |
| Tay Anderson Spotlight Cabaret Series - VIRTUAL | 5:00 pm |
| Christmas My Way: A Sinatra Holiday Bash | 7:30 pm |
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