The Hemingways' Michigan summers typically began when the school year ended and ended in late August. Grace would spend the entire time there assisted by a hired local girl or one brought with them from Oak Park. Doctor Hemingway joined them as much as his medical practice would allow.
When he was there, Dr. Hemingway loved to be outside. He gave his children swimming lessons and taught them how to safely deal with an overturned boat. Friends and family members also made frequent visits.
At the lake most of the time was spent outdoors where they swam, fished, roasted marshmallows, went boating, and sat around doing nothing. They also enjoyed playing dress up and entertaining family and friends. When Ernest tuned eleven years old, the family celebrated with 75 guests whose 20 boats filled the shore.
Another favorite activity was target shooting. Dr. Hemingway instructed all the children on gun safety and they enjoyed spending Sunday afternoons competing to see who was the best shot.
Carol Hemingway was born at Windemere during July 1911. Both she and Ernie shared July birthdays and a family tradition was started. Just before the birthdays, the family would walk into the woods where they would cut and bring back a "birthday tree." The tree would be placed on the screened porch and decorated much like a Christmas tree.
In 1905 Grace used money she, inheritance to buy a 40 acre farm across the lake from Windemere and "Longfield Farm" became a regular part of Michigan summers. Trees were planted there and with the help of local farmers, hay was cut and vegetables planted and harvested. As he got older Ernest enjoyed camping on the property while he worked there. In 1919 Grace had built a small cottage on the highest part of the property that she called "Grace Cottage." Here she occasionally spent time away from the hectic pace of her children.