Heywood was born on November 14, 1821, in Princeton, Massachusetts, to Ezra and Dorcas Hoar.

[2] In August 1848, he started the firm of Heywood & Warren in Hubbardston before buying out his partner and moving to Worcester in 1855.

[1][2] Heywood entered into a partnership with E. A. Goodnow in the wholesale and retail boot and shoe trade.

The retail business was taken over by Heywood, who continued it until 1864, when he began to manufacture boots and shoes.

[2][3] The main Heywood factory was built in 1879 on Winter Street, and was considered the largest and best equipped of its time.