Before the American Civil War, he and his wife Harriet Hayden aided numerous fugitive slaves on the Underground Railroad, often sheltering them at their house.

Located on the north side of Beacon Hill, the Lewis and Harriet Hayden House has been designated a National Historic Site on the Black Heritage Trail in Boston.

According to the principle of partus sequitur ventrem adopted by the slave states in the 17th century, the children's status in the colonies followed that of the mother.

He sold off the boy's brothers and sisters in preparation for moving to Pennsylvania; he traded 10-year-old Hayden for two carriage horses to a man who traveled the state selling clocks.

The travels with his new master allowed Hayden to hear varying opinions of slavery, including its classification as a crime by some people.

[4][5] When he was 14, the American Revolutionary War soldier Marquis de Lafayette tipped his hat to Hayden while visiting Kentucky.

The men were Lewis Baxter, an insurance office clerk, and Thomas Grant, an oil manufacturer and tallow chandler, and they did buy him.

[2][3][8] In the fall of 1844, Hayden met Calvin Fairbank, a Methodist minister who was studying at Oberlin College and had become involved in the Underground Railroad.

"[9] Fairbank and Delia Webster, a teacher from Vermont who was working in Kentucky, acquired a carriage and traveled with the Haydens to aid their escape.

The Haydens covered their faces with flour to appear white and escape detection; at times of danger, they would hide their son Joseph under the seat.

[9] Deciding he wanted to be at the center of anti-slavery activity, by January 1846 Hayden and his family moved to Boston, Massachusetts, which had many residents who strongly supported abolitionism.

"[19] In his history of that period, writer Stephen Kantrowitz wrote of Hayden: We do not know what route he took home from western New York to Detroit, nor what hardships he endured on the way.

Hayden prevented slave catchers from taking the Crafts by threatening to blow up his home with gunpowder if they tried to reclaim the pair.

Records from the Boston Vigilance Committee, of which he was a member, indicate that scores of people received aid and safe shelter at the Hayden home between 1850 and 1860.

Wallcutt and myself over to Lewis Hayden's house in Southnac Street, thirteen newly escaped slaves of all colors and sizes were brought in into one room for her to see.

Though Mrs. Stowe had written wonderful "Uncle Tom" at the request of Dr. Bailey, of Washington, for the National Era, expressly to show up the workings of the Fugitive Slave-Law, yet she had never seen such a company of 'fugitives' together before.Hayden opened a clothing store in 1849 at 107 Cambridge Street.

[9] The financial crisis of 1857 caused a decline in sales, so Hayden closed that shop and set up business in a smaller store.

[26] At a meeting at Samuel Snowden's [May Street Church], which included reading of the act, Hayden said: "... safety was to be obtained only by an united and persevering resistance of this ungodly law ..."[27] In American National Biography, Roy E. Finkenbine wrote: After the passage of the Fugitive Slave Act of 1850, Hayden worked tirelessly to fight its enforcement ... As a member of the executive board of the Boston Vigilance Committee, which was created to aid and protect fugitive slaves in the city, he often functioned as a liaison between white and black activists, including members of the Twelfth Baptist Church, to which he belonged.

[2][28][29] He played significant roles in the attempted rescue of Anthony Burns and in resisting legal authorities in the case of Thomas Sims.

[30] In addition, Hayden contributed money to abolitionist John Brown, in preparation for his raid on Harper's Ferry.

[36] Hayden was active in the Freemasons, which had numerous black members who worked to abolish slavery, including David Walker, Thomas Paul, John T. Hilton and Martin Delany.

[41][42] Following the war and emancipation, Hayden traveled throughout the South working to found and support newly established African-American Masonic lodges.

[46] Harriet died in 1894 and left $5,000, (~$157,564 in 2023) the entirety of their estate, to the Harvard University for scholarships for African American medical students.

Records from the Boston Vigilance Committee, of which Lewis was a member, indicate that scores of people received aid and safe shelter at the Hayden home between 1850 and 1860.