July
| 7 | 9:00 AM | First session of Pioneer School starts |
| 9 | 12:05 PM | Food For Thought, Sesquicentennial Highlights: Winona Around 1858, with James Erickson |
| 9 | 7:30 PM | Collector's Club |
| 10 | 7:00 PM | Civil War Roundtable |
| 12 | 10:00 AM | Spinners & Weavers |
| 14 | 7:00 PM | Quilt Guild |
| 21 | 9:00 AM | Second session of Pioneer School starts |
| 23 | 12:05 PM | Food For Thought Book Chat, While the Locust Slept, by Peter Razor |
| 24 | 1:00 PM - 3:00 PM | American Girl Club - Perforated Paper or Paper Lace project. |
| 30 | 12:05 PM | Food For Thought, John Deere meets Ali Babba: My Time in Iraq, with Major David Baer |
| 31 | 1:00 PM - 3:00 PM | American Girl Club - Perforated Paper or Paper Lace project. |
| 31 | 7:00 PM | Preservation as our Legacy with Bonnie McDonald |
August
| 4 | 9:00 AM | Third session of Pioneer School starts |
| 7 | 1:00 PM - 3:00 PM | American Girl Club - Trinket Box with Scrap Pictures project. |
| 9 | 10:00 AM | Spinners & Weavers |
| 11 | 7:00 PM | Quilt Guild |
| 13 | 12:05 PM | Food For Thought, Winona Lighting: Lighting as Part of the Construction Process with Steve Biesanz |
| 14 | 7:00 PM | Civil War Roundtable |
| 20 | 12:05 PM | Food For Thought, The Winona Port Authority and What We Do with Judy Bodway |
| 21 | 1:00 PM - 3:00 PM | American Girl Club - Trinket Box with Scrap Pictures project. |
| 27 | 12:05 PM | Food For Thought Book Chat, Water for Elephants by Susan Gruen |
| 27 | 7:00 PM | Driftless Area Rock Art with Robert "Ernie" Boszhardt |