Following his move to Middlebury, Vermont Painter served in numerous roles: a soldier, Jurist, Sheriff and State Representative.

He purchased fifty acres along Otter Creek, eventually building a number of mills and selling smaller plots of land or donating them for public buildings, including the courthouse and Congregational church.

During the American Revolutionary war, the town of Middlebury was evacuated, and Painter had left with the others but remained in the state.

[3] Painter served in a number of political offices: member of the Vermont Constitutional Convention (1777), judge of the Addison County Court (1785, 1787–1794), sheriff of Addison County (1786), and member of the Vermont House of Representatives (1788–1792).

[4][6] The cane has its own song, "Gamaliel Painter's Cane," penned in 1917:When Gamaliel Painter died, he was Middlebury's pride, A sturdy pioneer without a stain;And he left his all by will, to the college on the hill,And included his codicil cane.Oh, its rap rap rap, and it's tap tap tap, If you listen you can hear it sounding plain; For a helper true and tried, as the generations glide, There is nothing like Gamaliel Painter's cane.