Tom Maakestad works and lives in Marine on St. Croix, MN, where he has maintained a studio for the past 16 years. The Minneapolis area has been his home base since 1992. Prior to that, Tom and his wife, Anna, lived in Hong Kong for seven years, where they both had busy careers and traveled extensively throughout Asia. Trekking in Nepal, Burma, Indonesia, Malaysia, and Thailand, among other countries, gave them a firsthand observation of different cultures and art forms.

As a painter, Maakestad’s primary subject matter continues to be inspired by the broad valleys and agricultural regions near his family farm in Northfield, Minnesota. His landscape paintings have been included in collections at the Mayo Clinic and many others across the U.S. and overseas. The U.S. State Department purchased four of his southern Minnesota oil pastels for the ambassador's residence in Oslo, Norway.

Additionally, in the fall of 2016, he was invited to exhibit four paintings at the U.S. Embassy in Oslo. The exhibition, organized by the U.S. ambassador, brought together many luminaries of the Norwegian gallery and museum world.