I am having trouble googling this, surprisingly, it seems like a very obvious question, one that kids would ask teachers! I'm thinking this journey in all must have taken a couple of months? For funzies I was plugging in different starts and stops into Google Maps from the maps I can see on the internet trying to time it out, and for example the time to walk from Jackson MI to Lafayette IN would be about 27 days, and that's assuming you take the most direct route and can walk every day, which is certainly not feasible for escapes on the Underground Railroad. Also apparently most (??) of the people went all the way to Canada, which would take even longer.
So do we have any historic record of how long a trip would take, perhaps from the memoirs of Harriet Tubman or other conductors?
Not surprisingly, it varies tremendously. The Underground Railroad wasn't really a discrete thing, so much as the multiplicity of choices slaves made and the context they made them in. For example, William Wells Brown was a slave in Missouri, and when his master brought himself on a steamboat up to Cairo, Illinois, he took the chance to make a run for it. That very day, he'd made it to a free state, but that's not the end of his journey. He still had to escape slave catchers through a proslavery county in Southern Illinois; the journey that brought him in contact with the quaker Wells Brown took him several nights' journey through Southern Illinois in the winter.
One slave narrative, that of Caroline Hammond, details her family's escape from Southern Maryland to Pennsylvania; they traveled openly by wagon -her stepfather was a free man, and was able to bribe the county sheriff for a travel pass- to Baltimore, where they were sheltered by a white family who supported the Underground Railroad, and thereafter with no stops and avoiding every settlement to Pennsylvania.
Escapes could take very little time at all by ship; if slaves took control of a ship, or stowed away, they could be in a free state or a foreign country in a matter of days. It's hard to really conceptualize a 'typical' Underground Railroad journey, so how long it would take depends very much on the slave's location and the means chosen to escape.
As /u/dandan_noodles says, the Underground Railroad isn't a railroad like we would imagine...and like the first generation of historians told us. That railroad is a regular network of metaphorical trains that always run on time. The reality looks like a much more improvised set of overlapping networks that shift considerably based on local political climates, the allegiances of white facilitators, and the availability of funds. Every run is planned afresh, more node-to-node than start-to-destination.
For a very cleaned up example: Philadelphia and Baltimore, both of which have large free black communities, are popular places to hop on. (George Washington lost his slave Ona Judge in Philadelphia.) But you obviously can't stay indefinitely in Baltimore and Philadelphia can be risky, especially if you're from nearby. You want to get somewhere safer. That may be a farming region in southeast Pennsylvania, which becomes infamous for harboring fugitives. The local Quaker community is big into that and often hire fugitives on as laborers, short or long term. But Philadelphia might also pass you on to New York, where an independent organization (and later on, two of them) operate. This is more like "we know a guy" than "we refer you to our branch office."
They would put the fugitive on some form of transport (a literal railroad was an option) and arrange for someone to meet them at the station or dock. For quite a while, the most active figure meeting them seems to have been a guy named Louis Napoleon. Funds for the passage, and any necessary bribes, would come out of whatever the fugitive had on hand plus the accounts of the local vigilance committee. Fights over these funds, which often included donations from whites which got managed by blacks, could get serious and occasionally crippled or ceased operations.
Once the fugitive is in NYC, they become NYC's problem. That can mean being sent immediately on -NYC is a bad place to be a fugitive slave- but you might be sheltered for a few days in someone's home while the heat dies down and they make arrangements. High-profile whites are prominent in that because they leave large paper trails, but free black communities must have had a big role too. The next stop may be Boston or elsewhere in New England, where most fugitives can expect to live indefinitely prior to 1850. Slave catchers can try, but rarely succeed.
It can also mean the Burned-Over District of New York, an abolitionist and otherwise reformist hotbed where fugitives also live fairly openly. At one point, an antislavery convention is in town and they hear that some slave catchers have arrived and taken a fugitive to jail. They adjourned to take him out of the jail and get him across the lake to Canada. This is also where Frederick Douglass lives and he liked to brag about how many people he housed and sent on. (The chief of a different local operation pointedly left Douglass out of his account of things, because he was a diehard Garrisonian and Douglass broke with them very acrimoniously over strategy.) There are similar places where fugitives can live in relative safety further west, but I don't know much about them beyond that they existed.
The Fugitive Slave Act of 1850 changes all that. Now aiding fugitives is a crime that can have serious punishments. You can even be prosecuted for failure to actively assist in recapture and rendition. There's no time limit on recapture too, so people who have been living safely in the free states for decades, and their kids, are now in danger. At that point Canada becomes the one safe place, at least for a while. We don't know just how many, but probably about twenty thousand people decamp for freedom in the British empire at least temporarily. Once widespread resistance to fugitive renditions becomes more the norm, some come back.
Which is all a long way to say I can't help much with a typical time either. It could take only a few days to get to a free jurisdiction, or fugitives might hide out for months before crossing the right state line. If we narrow it down to Tubman, then we can get some data points. Tubman didn't write memoirs herself that I know of, but the biography I generally see cited (and have not read, sadly) is Kate Larson's Bound for the Promised Land. Eric Foner goes into a little bit of detail on two of her 1856 rescues. (Tubman went back into the South at least thirteen times.) Tubman is unusual in a lot of ways, but she did rely on Underground Railroad networks so she's not completely out there to use as an indicator.
Twice in 1856, Tubman brought fugitive slaves through Sydney Howard Gay's office in New York City. In May, Gay recorded, "Captain Harriet Tubman" arrived with four fugitive slaves-Ben Jackson, James Coleman, William Connoway, and Henry Hopkins-from Dorchester County on Maryland's eastern shore, the center of slavery in the state. As young men in their twenties, the four had an "aggregate market value," Gay estimated, of $6,000.
Since he had her there, and appears to have known her previously, Gay quizzed Tubman about her career and just what went into this particular rescue.
The group started out on foot from Maryland on May 3, 1856. When they reached New Castle, Delaware, having learned that the owners had raised a "hue and cry" and posted a substantial reward for their capture, the fugitives hid for a week in a "potato hole" (presumably a kind of root cellar) at the home of a black woman. At great risk, Tubman traveled back and forth to Wilmington by train seeking assistance; eventually she persuaded "a friend" to bring the slaves to Garrett's house in that city, where they arrived on May 11. They appeared at William Still's office in Philadelphia two days later, and then contiinued on by rail, reaching Gay's on May 14. Gay dispatched them all to Syracuse, from where they headed to Canada. Three of the four men appear in the Canadian census of 1861, living in or near Toronto.
No dates for arrival in Canada. Sorry.
Tubman was at it again in November, aiming to get her sister. The sister wasn't ready to go. (Imagine that conversation.) She picked up William & Josiah Bailey and Peter Pennington instead. Tubman took them the long way to Wilmington, on foot for ninety miles. On the way, an Eliza Manokey who had escaped and hid in the homes of free blacks joined up. Once more rewards were posted
Thomas Garrett, however, managed to get black bricklayers to convey them, concealed in a wagon to William Still's office in Philadelphia on the night of November 24. Still immediately sent them, separately to New York where they arrived on November 26 and 27. Gay then dispatched them to Troy and Syracuse.
In Syracuse, they found an operator known to Tubman. He was all tapped out just then and so the usual option to take the fugitives across the Niagara Falls Suspension Bridge wasn't available. Then ended up taking a different route through various "half way houses". But they got there. No finish date again. :(
Sources
My quotes are from Eric Foner's Gateway to Freedom: The Hidden History of the Underground Railroad, which is mostly about the New York operation.
