1. The first official U.S. postage stamp featuring a Maine theme was issued on May 29, 1959. The stamp depicted the state flower, the white pine cone and tassel.

2. On May 29, 1630, John Winthrop and his group of Puritan settlers arrived in what is now Salem, Massachusetts, after sailing from England. Many of these early colonists later settled in Maine.

3. May 29, 1911, was the opening day of the inaugural game at the new Wrigley Field in Chicago. The stadium was built by Maine businessman Charles Weeghman, who owned the Chicago Whales baseball team.

4. The Maine International Film Festival, one of the state's largest cultural events, begins each year on the last Friday in July. The festival's opening day has fallen on May 29 several times in recent years, including 2015 and 2020.

5. In 1949, on May 29, two alumni of the University of Maine – Arnold K. Lowell and Sumner T. Pike – created the first "Maine Day" celebration. Maine Day is still observed at the university today as a day of student and community service.