While at Williams, Rogers also taught and served as principal of the Sanderson Academy in Ashfield, Massachusetts.

After his term of service expired in 1863, Rogers served in the United States Christian Commission and resumed teaching.

[3] He spent a year teaching at the Douse Academy and from 1864 to 1866 was the principal of Natick High School.

Rogers was the first person outside of the Howe family to own the Inn, which was built after King Philip's War.

Howe and Rogers spent a considerable amount of money renovating and improving the building.

In 1897 the pair sold the Inn to Boston businessman Edward Lemon.