In 2233, she gave birth to James early because she accidentally tripped over one of the farm pigs (TOS novel Enterprise: The First Adventure). The Kirks were farmers because George thought it was an appropriate job for Back-to-Earthers (TOS novel World without End).
Winona firmly believed that taking part [in a race] was more important than winning. James did not share his mother's belief (TOS novel The Great starship Race).
Winona joined the rest of her family on planet Grex in 2248, but remained unaware that James got swapped for his 2266-self during that time (TOS novels The Janus Gate: Present Tense, The Janus Gate: Past Prologue and The Janus Gate: Future Imperfect).
When she joined her sons to see George off as he launched for planet Hellspawn in Late 2249, James insulted George so vehemently that - after George's ship had left - Winona publicly slapped James across the face and walked off (SNW story First star I see Tonight and TOS novels Final Frontier and Crisis on Centaurus).
Following the death of her husband, Winona left Earth in 2259, to stay with her eldest son and his family on Deneva (TOS novel The Last Roundup), but returned within a few months (SNW story First star I see Tonight).
In 2263, Winona and her eldest son attended the change of command ceremony of the USS Enterprise (NCC-1701) from Captain Christopher Pike to James T. Kirk(TOS novels: Enterprise: The First Adventure and Final Frontier).
Winona cared for the Kirk farm alone for seventeen years. In 2269, a fire there failed to kill her. However, a second fire broke out on June 2, 2283 and Winona sadly died later that day of pneumonia, caused by smoke inhalation. As per her wishes, she was cremated and her ashes were placed in a wall crypt in a chapel that stood in Riverside (SNW story First star I see Tonight and TOS novel Time for Yesterday).