After working in Philadelphia as a clerk in the U.S. Treasury Department, he later read the law and practiced as an attorney in Washington, DC.

While living in Washington, D.C., Woodward was described as "a man of middle age, a hardened bachelor who wore nut-brown clothing .

Woodward, with Governor William Hull and associate Justices John Griffin and Frederick Bates, possessed all the legislative power in the Territory.

In 1807 as Territorial Justice, he refused to allow the return of two slaves owned by a man in Windsor, Upper Canada (present-day Ontario).

While Hull and Justices Bates and Griffin left, Woodward stayed and maintained his judicial status in Detroit during the British occupation.

Following the destruction of Detroit in the Great Fire of 1805, it fell to Woodward and Hull to oversee the rebuilding of the then territorial capital.

The resulting plan drew heavily from Pierre L'Enfant's layout for Washington, D.C.[5] Woodward proposed a system of hexagonal street blocks, with the Grand Circus at its center.

Most prominent of these are the construction of the six main "spokes" of Woodward, Michigan, Grand River, Gratiot, and Jefferson avenues and Fort Street.

Woodward, somewhat in jest, claimed the road's name was simply related to the fact that it traveled toward the wooded area to the north of the city.

It is likely that a series of Indian trails once radiated from the approximate location of the Campus Martius and this may have inspired the choice of a radial geometry for Woodward's city plan.

John Monteith and Father Gabriel Richard, Woodward drafted a charter for an institution under the name of the Catholepistemiad or the University of Michigania.

The Catholepistmiad originally had the authority to "establish colleges, academies, schools, libraries, museums, atheneums, botanical gardens, laboratories, and other useful literary and scientific institutions consonant to the laws of the United States and of Michigan, and provide for and appoint Directors, Visitors, Curators, Librarians, Instructors and Instructrixes among and throughout the various counties, cities, towns, townships, or other geographical divisions of Michigan.

August 26, 1824, saw Woodward's return to the judiciary, as President James Monroe appointed him to a judgeship in the new Territory of Florida.