Milton Kennedy is remembered as one of the most outspoken abolitionists in the city of Portsmouth, Ohio. He helped Freedom Seekers find safe passage on the Underground Railroad. In 1852, Kennedy built the first three-story building on Second Street and opened a feed and seed store on the ground floor. Soon he would be joined in the business by his brother-in-law, Joseph Ashton, who was also a vocal abolitionist and agent of the Underground Railroad. Kennedy was a founder of the Republican Party in Scioto County, the State of Ohio, and the United States, having attended and served as a delegate at the first meetings of these organizations. He was among only a handful of supporters of the Free Soil Party in Scioto County in the 1850s. Both he and Joseph Ashton belonged to Portsmouth's "Radical Church," an antislavery Methodist society, which met on Fifth Street.