Wednesday, July 12, 2023
| 7:00 pm | Square Dancing – Kaleidoscope Squares |
Thursday, July 13, 2023
| 9:00 am | Winona County Soil & Water Conservation District Meeting |
| 2:00 pm | Recognition Program |
| Crowning of Fair King & Queen | |
| Winona County Outstanding Senior Citizens Presentation | |
| Hall of Fame Introductions | |
| SWCD Outstanding Conservationist Award | |
| Winona County Farm Family Recognition | |
| Winona County Century Farm Recognitions | |
| 6:00 pm | Brad Boice (Elvis and the Classics) 2 hour show |
| 8:00 pm | Eric Ebert Wisconsin’s Favorite Neil Diamond Tribute Artist 2 hour show |
Friday, July 14, 2023
| 4:00 pm | Pedal Pull |
| 7:00 pm | music by Gate City Jazz Band from Winona, MN |
Saturday, July 15, 2023
| 10:00 am | Horseshoes Contest at the St. Charles Moose Club |
| 11:00 am | Spinning and Weaving Demonstration by Lisa Douglas |
| 12:00 pm | Memorial Lego Building Contest for Kids and Adults (bring your own Legos) |
| 1:30 pm | Charcuterie Board Contest |
| 2:00 pm | Fastest Fingers in the West Contest – for knitters and crocheters |
| 2:30 pm | FROZEN T-shirt Contest |
| 3:00 pm | Vegetable Carving Demonstration by Jie Schloegel |
| 4:00 pm | music by the Grass Run Band (bluegrass) |
| 7:00 pm | Open Class Talent Show |
Sunday, July 16, 2023
| 9:00 am – 12:00 pm | Pancake Breakfast by the St. Charles Lions Club |
| 10:30 am | Ecumenical Service hosted by First Presbyterian Church with Reverend Tammy Rider |
| 12:30 pm | music by The Bandanas |
| 2:00 pm | music by RavensFire Band (Irish, Folk & Americana) |