The house design is based on the artwork of William Donahey, an author-illustrator who created the Teenie Weenies cartoon characters that were two inches (5.1 cm) tall[2][3] and lived under a rose bush in a pickle barrel.

He created the Teenie Weenies cartoon feature,[6][7] which was a widely syndicated comic that debuted in the Chicago Tribune in 1914.

[8] In the early 1920s, Donahey contracted with the Reid-Murdock & Company of Chicago to allow use of the Teenie Weenie characters to promote their Monarch Foods line.

[8] Teenie Weenies subsequently appeared on many of the labels of Monarch food products aimed at children, including toffee, peanut butter, popcorn, and all kinds of canned vegetables.

The signature product was Teenie Weenie Sweet Pickles, which were sold in a small wooden keg that could be refilled by the grocer.

[4] In 1926, Reid-Murdock decided to create a life-sized version of the small pickle house featured in the ad, and construct it near Grand Marais, where the Donaheys liked to vacation in the summer.

Pioneer Cooperage first built it in Chicago at their workshop, then took it apart and shipped it to Grand Marais, where it was assembled outside of town on the shore of Sable Lake.

[4] The Donaheys then built a log cabin on the spot where the barrel house had stood, and they continued to summer in Grand Marais for many more years.

[4] On July 3, 2005, after much work and with a budget of $125,000 (equivalent to $187,000 in 2023[9]) in expenses the renovated Pickle Barrel House was opened to the public.