The Albert Tresslers of Madison, Wisconsin began vacationing in Door County in the late teens, staying at Jacksonport's LaMere Lodge. In 1920, they bought land on Elmira Beach, about 2.5 miles north of Jacksonport and in 1922, they had their Summer cottage built, which later became known as Grandma's Cottage.
In the early years, Arlouine (Grandma) Tressler would spend Summers in Door County, while Albert (Grandpa) Tressler would travel back and forth to Madison where he was a prominent banker. Later, Arlouine would live full-time in Door County with Summers in the cottage and Winters in a small cottage on the property.
The family lost Albert in 1951 and Arlouine in 1961. Their daughter Alice, who married local carpenter Ben Olson also lived full-time on the property, raising their son Jay Tressler Olson. Jay and his wife Penny continued to reside in what is now Greenwood Cottage, raising their sons Ben Olson and Matthew Tressler Olson at this great location. Today, Penny is the owner of the cottages and is assisted by husband Glenn Hasenjager and son Ben Olson in managing the property and cottage business. Ben's sons Jay and Zach, along with Ben's wife Lisa and daughter-in-law Stacy continue the tradition of maintaining the family's Door County compound. And now, the 6th generation of the family, Josephine has joined the family and will have the opportunity to spend Summer weekends in the very spot where her Great, Great, Great Grandparents first built Grandma's Cottage 99 years before her birth.
First known as Tressler Cottages, then Ben Olson Cottages and now simply Olson Cottages, our family continues to welcome guests to Grandma's Cottage, Redwood, Twin Cedars and Greenwood Cottages where the tradition of family and the simple pleasures of a beach vacation endure.
To help celebrate Grandma's Cottage's 100th anniversary, we look at some images from the decades...