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“Family Album”

 

Grandma’s Cottage

 

Redwood Cottage

 

Twin Cedars Cottage

 

Greenwood Cottage

 

Jacksonport Swamp Beach and Social Club

 

 

 

 

 

 

 

 

 

Now in its fifth generation

of enjoying this beautiful

property, the Olson

family includes an

extended group of families, including past and present guests that have brought

these cottages to life over

the last 80 years!  

The Albert Tressler family of Madison, WI first started

visiting Door County in the late teens, staying at LaMere Lodge in nearby Jacksonport.  Soon after they purchased the real estate that is now Olson Cottages.  They had the first cottage, Grandma’s Cottage, built in 1922 and began to use the cottage seasonally. 

 

Albert and Arlouine’s family was growing and as time went by, additional cottages were built to accomodate the growing family and hosting occasional renters.  Redwood came next in 1931, and the Honeymoon Cottage sometime after that.

 

Arlouine and Albert’s son Irving went on to write for Life and Scribner’s magazines and authored a number of books including the best-selling “How to Lose Friends and Alienate People.”  Son Willis pursued a career in the sciences and later spent time on the Antarctic continent.  

 

In the early 40’s, daughter Alice married local carpenter Ben Olson, and they added Twin Cedars Cottage and a son, Jay, to the line-up.  Through the years, other cottages were added, including Green Tree, Birchwood and Greenwood Cottage. 

 

In 1958, Ben built Alice’s dream house just to the south of the cottages.  This expansive ranch was sold after her death in 1963.  In 1999,  Penny Olson, Jay’s wife and current owner of Olson Cottages, bought back the home, named “Penny’s Quarters” and now makes it her permanent home. 

 

The Honeymoon Cottage was razed in the early 60’s and Twin Cedars was moved to its current location. Green Tree was sold to the Gilbertson family and Birchwood was rebuilt to be the home of Ben Olson

and his second wife, Jinx.  

 

Meanwhile, Ben and Alice’s son Jay Tressler Olson and his family made the green house (now named Greenwood Cottage) their family home.  Having lost both Ben (in 1993) and Jay (in 1999), today Penny along with new husband Glenn Hasenjager, and Jinx reside in these homes, while Grandma’s Cottage, Redwood, Twin Cedars and Greenwood Cottage are available for rental. 

 

Known originally as Tressler Cottages, then Ben Olson

Cottages, and now simply Olson Cottages, the family has been through many changes, but the spirits of Albert, Arlouine, Alice, Ben and Jay are still alive and guide the current generations in their periodic

updating of the property.

  

     Throughout the years, one thing has been a constant, and that has been the steadily growing list of families who have made these cottages their summer retreat. 

Many have since bought or built (most by Ben Olson)

their own cottages nearby, but began their Door

County experiences right here at Olson’s. 

 

These families have become a part of these cottages           

            and a part of the Olson family.  Their names fill old and new guest books;  Hyson, Haynes, Gilbertson, Nardi, Slepicka, Stoerzbach, Brownell, Van Trigt, Noyes, Wermich, Hanks, O’Dell, Barney, Grinton, Grogan, Shaw, Cassens, Juers, Bruch, Lagesson, Breithaupt, Hendrickson, Dalla Santa, Frankow, and so many others.  While the cottages are wonderful, it has been these people who have brought them to life throughout the years, and added so much warmth to the cottages and the Olson family.

 

     Olson Cottages are now owned by Penny Olson, who runs them with the help of her husband Glenn.  Penny’s grandchildren also spend time each summer on the beach. Here, Jay W., Zachary, Haley, Brittney, and the newest grandson, Jacob Tressler Olson do and will enjoy the simple pleasures that their Great-Great-Grandparents, Albert and Arlouine Tressler, first enjoyed

almost 90 years ago.

O  L  S  O  N    C  O  T  T  A  G  E  S

Photos Above, Left to Right;

 

One:  Arlouine Tressler is the original “Grandma” in Grandma’s Cottage.

 

Two:  Ben and Alice Olson enjoy an evening out at Green Tree Cottage in the 50’s.

 

Three:  Jay Olson and Grandson Jay W. Olson enjoy a typical moment at the family picnic table in 1995.

 

Four:  The current generation (Circa 2000) of Olsons, led by Penny Olson (left) welcome you to share their vintage cottages.

H   I   S   T   O   R   Y

Home  ■   Grandma’s Cottage  ■  Redwood Cottage  ■  Twin Cedars Cottage  ■  Greenwood Cottage

Above: The great-grandsons of Ben and Alice Olson and the great-grandsons of Dottie and Gil Gilbertson enjoy a beach moment in the late 90’s.  Like their parents, grandparents and great-grandparents, the beach friendships continue each summer.  Below:  Their Grandmothers, Pauline Gilbertson Geisler and Penny Olson enjoy a quiet moment in comfortable beach chairs.