| Holiday Lights & Festive Sights | - | |
| Wonderland in Lights | - | |
| Live Music: Taylor Steele & the Love Preachers | 12/06/2019 | |
| Live Music: Fairly Odd Duo | 12/06/2019 | |
| Live Music: BreakAway | 12/06/2019 | |
| Larry the Cable Guy at Effingham Performance Center | 12/06/2019 | |
| Live Music: Superbad | 12/06/2019 | |
| Live Music: The Britt Black Bands Mid-Winter Blast | 12/07/2019 | |
| Breakfast with Santa | 12/07/2019 7:00 AM - 11:00 AM | |
| Santa Claus at First National Bank of Waterloo Effingham Location | 12/07/2019 9:00 AM - 12:00 PM | |
| Winter Market | 12/07/2019 9:00 AM - 12:00 PM | |
| Meet the Author: Ron Kinder | 12/07/2019 11:00 AM - 1:00 PM | |
| Benefit for Zac Johnson | 12/07/2019 3:00 PM - 9:00 PM | |
| A Christmas Story presented by Three Chicks & a Stage at Effingham Performance Center | 12/07/2019 7:00 PM | |
| Live Music: Too Far Gone | 12/08/2019 | |
| Santa is Coming to the Winery | 12/08/2019 | |
| A Christmas Story Presented by Three Chicks & a Stage at the Effingham Performance Center | 12/08/2019 2:00 PM | |
| Bingo Night at Effingham Event Center | 12/10/2019 7:00 PM - 10:00 PM | |
| The Wines of Tuck Beckstoffer | 12/11/2019 | |
| Books & Brews Book Pairing | 12/11/2019 7:00 PM | |
