There were many towns and cities in the North with connections to Underground Railroad activity and, not surprisingly, many of these cities and towns were located in an region called the Borderland, the geographic area located along the borders between free and slave states. The most well-known border was the Ohio River. Underground Railroad activity was strong in places such as Cincinnati, Oxford, and Ripley, Ohio. In Indiana, Richmond, Madison, and Newport (today, Fountain City) had many conductors of the Underground Railroad. Further east, especially in the active region of the Chesapeake Bay area, cities such as Philadelphia and Baltimore were hot spots. Further north, Boston, Massachusetts, and Rochester, New York were also strongly involved.
While some fugitive slaves settled in the cities and towns they reached after entering the North, many enslaved individuals wanted to continue their journey all the way to Canada. Slavery was illegal in Canada and there were no laws in place protecting slave owners or slave catchers. It was by far the safest place a fugitive slave could be. The province of Ontario had the largest population of free slaves, a number estimated at around 17,000. Many of the fugitive slaves entering this area of Canada came through either Ohio or New York.
Slaves in Virginia and North Carolina sometimes found shelter in the Great Dismal Swamp, a thousand square-mile area of forested peat bog along the border of these two states. The density of vegetation and the difficulty of traveling through the swamp made it an ideal hiding place for escaping slaves. The communities in the Great Dismal Swamp are examples of so-called maroon communities, or permanent settlements of fugitive slaves that existed all over the South in areas of thick forest or dense swamps.
Early in United States history, several parts of the country were controlled by Spain or Native American populations. Enslaved individuals were often able to escape and find assistance at the Spanish-controlled Fort Mt. Mose in St. Augustine, Florida, or with Seminole populations in other parts of Florida. While Underground Railroad activity was concentrated mostly in the regions of the Ohio River and the Chesapeake Bay, many enslaved individuals escaped further south to the regions controlled first by Spain and later by Mexico. Though these areas saw very little Underground Railroad activity, many enslaved individuals escaped there seeking their freedom.