[1] Freeman attended the Wright Flying School on Long Island, New York, where he was instructed by Arthur L. Welsh.
He assisted Welsh and did some flying during Robert J. Collier's October 1911 aerial exhibition at his estate outside Wickatunk, New Jersey.
[1] That May he became an assistant flying instructor at the General Aviation Corporation flight school at Atwood Park in Saugus, Massachusetts.
[1] On May 20, 1912, Freeman and Waite took part in a mock bombing of Fort Heath, Fort Banks, and the battleships New Jersey and Rhode Island (which were anchored Boston Harbor) by dropping sacks of flour with a note stating "What if this bomb, instead of flour, contained nitroglycerin's deadly power?"
[3][5] During the meet, Atwood was granted permission by the United States Postmaster General's office to operate an airmail route between Lynn and Saugus.
[1] After leaving Atwood Park, Freeman flew in exhibitions throughout New England and worked as a flying instructor for various companies.
In 1912 he participated in a meet at Harvard Aviation Field that included Lincoln Beachey, Philip W. Page, Glenn L. Martin, Charles K. Hamilton, Blanche Stuart Scott, and Harriet Quimby.
[1] Because Freeman participated in the unsanctioned meet he was suspended by the Contest Committee of the Aero Club of America.
[7][8] In the fall of 1912, Freeman performed at exhibitions in Chicago, Illinois, Newark, Ohio, Suffolk, Virginia, and Louisville, Kentucky.
The engine failed once more on the third takeoff, however a strong wind prevented Freeman from making the 360° turn needed to land the plane and it forcefully struck the ground.