Resort History

The Jackson family remains committed to providing sportsmen and families a great place to spend time in the woods and enjoy the lake. Learn about how the oldest resort in the Northwoods started and passed from generation to generation.

Jackson’s Lakeside Cottages was originally started by Frank Carley in 1901. Carley started with four cottages and also had 79 acres of farmland. It was the first resort on Little St. Germain Lake.

George H. Jackson bought the property from Carley in the fall of 1920 after selling Red Oak Resort to Walter DeHaas. George H. died only two years later and ownership went to his wife Catherine. After her death in 1929, Art and Anna Jackson ran the resort. It was during this period that Jackson’s Lakeside Cottages grew to be one of the most well known resorts in the area.

Most of the Carley built cottages were replaced in the 30’s and 40’s under Art and Anna’s stewardship. Art built the main lodge in the spring of 1935 and it is one of the last remaining Northwoods classics left from that era. Art Jackson guided the guests and ran the resort with the help of his two daughters and their families during the 1940’s. Lillian and Spike Lantz, and Helen and Sig Kaminski. Once World War II was over, their son, George A. Jackson was able to join the effort.

This was a transitional period for the resort as the automobile was being used more than the train to go on vacation to Northern Wisconsin. Families would stay for several weeks as the trip from Illinois, Indiana, and Iowa would sometimes take days. We have a handful of guests whose families began the tradition of coming north to Jackson’s Lakeside Cottages during this period and still come to visit us today.

A young Lieutenant George A. Jackson home on leave in 1943 with his mother Anna. He fought with the 83rd Division and was part of the first American troops to cross the Rhine River into Germany in the spring of 1945. During the war, he was awarded 2 Purple Hearts and The Bronze Star for his action against the enemy. After being promoted to Captain, George spent three years in Europe before returning home.

During the late 30’s and 40’s, several of the old cabins that dated back to the earliest days of the Frank Carley era were torn down and replaced. During this period, the Oriole, Birches, Jack, Jill, Idle Hour, Badger, Norway, and Martin were all built. Renovations were done to the Sleepy Hollow, Chicago, and Hammond. The main Lodge was also built in the spring of 1935. An old store that sat near the location of the swings and volleyball net was moved in 1940 and connected to the Lodge. It was converted into the new bar and “Tap Room” where only adults were welcome. Kids were allowed to play games in the Lodge area, but Mrs. Jackson kept the young ones out of her “Gremlin Garden”.

Art passed away in the spring of 1953. Anna ran the business with the help of her son George and his new wife Janet.

During the 1950’s and 60’s, Jackson’s enjoyed great notoriety and success as Little St. Germain lake gained publicity with its ability to produce fish. It has always been a great place for fishing, but by the early 60’s, people were discovering that this was also a great family destination. The clientele began to change and the resort was becoming a place where kids and families would escape the hustle and bustle of the city.

George A Jackson and his wife Janet took over ownership of Lakeside Cottages in the summer of 1969 after Anna’s passing. They undertook the task of updating the cottages to the more modern style of rental unit that the vacationer was looking for. Updated kitchens and remodeled bathrooms were the main projects that kept them busy. They provided a great atmosphere for the guests and made the customers feel like they were a part of the place. During the period of their ownership, they forged lifelong friendships and got to know many of the guests like family. It’s been since 1989 that George has been gone, but the impact that he left will always be present. We lost Janet in 2010, but her leadership and wisdom will be with us as long as the sign says “Jacksons”.

Brothers Tom and Ken Jackson and their families now own and operate Jackson’s Lakeside Cottages. They are the fourth generation of owners on the Little St. Germain property and are continuing to expand and improve the features so the guests have more to enjoy. Since they have been involved, there has been construction projects that has the resort on the right track for the future. Several remodeling projects have been done to the older cabins including the Birches, Jackson, and Homestead to better suit our current guests. A number of new construction projects have occurred in recent years including the Grand View, Hammond, Whitetail, and currently the Jack and Jill.