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This story of the Tilly escape is a free excerpt from the Secrets of the Eastern Shore guidebook, Tubman Travels: 32 Underground Railroad Journeys on DelmarvaMore information about the book, including where to buy it in stores and online, is available here.

Tubman Travels: 32 Underground Railroad Journeys on DelmarvaBIG PICTURE: Tricks of the Trade

Back during the Ottoman Empire, a German military commander named Helmuth von Moltke came up with a turn of phrase that has been a go-to aphorism in military circles for centuries now. It goes like this: “No battle plan survives contact with the enemy.”

This bit of wisdom might just as easily have been invented along the Underground Railroad. There, even the best-laid plans could go awry at a moment’s notice. One day it might be severe weather mucking things up. The next, it might be the sound of bloodhounds, or the appearance of a reward poster. The day after that, who knows—a broken-down wagon, a leaky boat, or a chance encounter with the wrong person?

Conductors and station masters had to be fast on their feet. The flexibility and creativity they brought to moments of crisis often made the difference between freedom and failure for fugitives. Harriet Tubman excelled in dicey moments—she could improvise with the best of them, and her skills in that regard come into play in this story of an escape in which she played the role of Cupid, reuniting a couple who had been kept apart for seven long years.

SETTING: A Lovesick Client

The lovesick man who approached Harriet Tubman at some point during 1856 remains unnamed in historical records. An escaped slave from Baltimore, he told Tubman the story of how he had been betrothed to a girl named Tilly and how he had to leave her and run away to freedom after hearing rumors that his owner was going to sell him off.

Seven years had passed since he made that escape. Now, he was hearing through the Underground Railroad grapevine that Tilly’s master was about to marry her off to someone else. Worried that he would lose her forever, this man hired Tubman to go get Tilly in Baltimore and bring her to him up in the North.

He gave Harriet the money he had been putting aside in some sort of “Free Tilly” fund. It’s not clear to me from my reading how often Tubman hired out her services as a conductor, or how those arrangements worked, exactly. But in his account of the Tilly escape, Tubman’s friend Thomas Garrett puts the transaction as plain as can be: “He gave Harriet money, and Tubman made her way to Philadelphia.” (She would make her way to Baltimore from there.)

The possibilities are endless. It may be that Tubman guesstimated the costs involved in an operation and asked clients to cover the cost of keeping runaways in food, shelter, disguises, and other essentials. With bounty hunters and police in pursuit, they might also need forged passes, train tickets, ferry rides, and who knows what else—often on a moment’s notice.

It’s also possible that Tubman charged rates that would generate a profit after expenses, something that some other conductors were known to do. Later in life, Tubman would demonstrate a strong entrepreneurial streak, starting up several different small businesses in upstate New York. Perhaps she sometimes applied a small-business mindset to her work on the Underground Railroad, generating profits that could then be applied to support future missions and finance rescues of her own family members.

Harriet arrived in Baltimore that October. She managed to locate Tilly despite the fact that the girl was in hiding from her master. There is no telling what plan Harriet had in mind originally for this “young and pretty mulatto.” Tubman biographer Sarah Bradford makes mention of a steamboat that she had planned on boarding being “disabled” and unavailable. Perhaps that boat had a friendly, familiar face among the crew that Harriet knew she could count on.

She had arrived in Baltimore with a letter signed by another such friendly face, a steamboat captain in Philadelphia. This note offered assurances that Harriet was a free resident of that city. She had no such note for Tilly, however.

SAILING: A Nanticoke Journey

Balitmore Inner Harbor, 1850

A view of Baltimore’s Inner Harbor from Federal Hill in about 1850, not long before Harriet Tubman engineered the Tilly escape.

In order to transport a black woman without proper paperwork into a northern port, steamships required a steep cash bond. Harriet didn’t have the money for that bond. Instead, she and Tilly ran a misdirection play, by heading south instead of north. They boarded the steamboat Kent at Dugan’s Wharf in Baltimore. (That wharf was located in the midst of today’s touristy Inner Harbor, near the Marine Mammal Pavilion of the National Aquarium. The image up top here is not of the Kent; it is, however, a typical passenger steamboat from roughly the era of this escape.)

The trip aboard that vessel started with a harrowing moment. Here is Bradford again:

They joined the stream of people going up to get their tickets, but when Harriet asked for hers, the clerk eyed her suspiciously, and said: “You just stand aside, you two; I’ll attend to your case bye and bye.”

Harriet led the young girl to the bow of the boat, where they were alone, and here, having no other help, she, as was her custom, addressed herself to the Lord.

Kneeling on the seat, and supporting her head on her hands, and fixing her eyes on the waters of the bay, she groaned:

“Oh, Lord! You’ve been wid me in six troubles, don’t desert me in the seventh!” [This is likely a reference to the fact that this was Tubman’s seventh rescue mission.]

“Moses! Moses!” cried Tilly, pulling her by the sleeve. “Do go and see if you can’t get tickets now.”

“Oh, Lord! You’ve been wid me in six troubles, don’t desert me in the seventh.”

And so Harriet’s story goes on in her peculiarly graphic manner, till at length in terror Tilly exclaimed: “Oh, Moses! the man is coming. What shall we do?”

“Oh, Lord, you’ve been wid me in six troubles!”

Here the clerk touched her on the shoulder, and Tilly thought their time had come, but all he said was: “You can come now and get your tickets,” and their troubles were over.

That boat was headed down the Chesapeake Bay to the mouth of the Nanticoke River, a good way below the Choptank River and the landscape where Harriet had been born and raised. As far as historians can tell, this would be the farthest south that Tubman ever reached in her work on the Underground Railroad. Then the Kent turned upriver and made its way up into Delaware, docking in the town of Seaford.

Along the way, Tubman had somehow managed to convince the captain of this steamboat to write a new letter saying that both she and Tilly were free residents of Philadelphia. One theory here is that perhaps this captain trusted Tubman’s word because he knew and trusted the captain who had provided Tubman with that first letter. Another possibility is that he was sympathetic to the cause of runaways. Who knows? Perhaps it was a combination. Whatever the case, that letter would soon come in handy.

OVERLAND: From Seaford to Freedom

When Tubman and Tilly disembarked in Seaford, they most likely did so at the location of the modern-day Riverwalk on the banks of the Nanticoke River just southeast of the Market Street bridge in the downtown area. As of this writing in 2017, there was quite a lot of construction going on along Seaford’s waterfront. A condominium complex was going up on the other side of that bridge. Storefront banners nearby were touting new retail and office spaces as coming soon.

High Street in Seaford in the 1860s

This is what High Street in downtown Seaford, Delaware looked like a few years after Harriet Tubman engineered the Tilly escape.

From that Riverwalk spot, Tubman and Tilly walked uphill to the Coulbourn Hotel, which stood on the site of today’s Gateway Park, a triangular bit of green space bordered by Market, High, and Front streets. There are benches there, and a pretty fountain. There is also a marker commemorating the day that Tubman and Tilly came through town.

The main commercial corridor in downtown Seaford runs along High Street, to the west. Restaurants and shops lie in that direction, along with the Seaford Museum, which is housed in an expansive old post office and features lots of interesting exhibit materials, including one section related to the story of Tilly and Tubman.

That story picks up again back at the Coulbourn Hotel, where Tubman seems to have taken the full-of-bluster-show-no-fear approach to her situation. As Thomas Garrett describes it, “she boldly went [into] the hotel and called for supper and lodging.”

The next morning, on their way out of the hotel, a slave catcher accosted Tubman and Tilly and demanded to know their legal status. Tubman showed off that letter saying she and Tilly were free. The innkeeper apparently intervened here, too, telling the slave catchers to leave his paying guests alone.

From Seaford, Tubman and Tilly either walked or took a carriage 10 or so miles north to Bridgeville. From there, they boarded a train to Camden, where they hired a carriage to take them to Wilmington. They eventually arrived at the home of Tubman’s friend, Thomas Garrett, who soon afterward wrote a letter to a friend dubbing the Tilly escape a particularly “remarkable” affair that had “manifested great shrewdness” on the part of Tubman.

[T]he strangest thing about this woman is, she does not know or appears not to know that she has done anything worth notice. May her Guardian continue to preserve her many perilous adventures.

Harriet Tubman: The DreamerTricks of the Trade

There are countless other examples of Tubman employing creative tricks while conducting her charges to freedom. She would give sedatives to young children to keep them quiet. She would hide slaves in cramped underground potato holes. She would use songs to convey coded messages.

Once when she was back on her home turf of the Eastern Shore, disguised in a bonnet and carting along two chickens as if on a routine errand, she encountered a man described by a biographer as a “former master” (it’s not clear who this might have been). She let those chickens loose, making off like it was an accident, and “all of the bystanders roared with laughter as she chased after them.” That man never recognized her amid the hubbub.

There is another story—whether legend or truth, it’s hard to tell—of a day when Tubman was on a train and saw a white passenger who might recognize her. She picked up a newspaper or book of some sort and pretended to read, even though she was illiterate. That man knew she couldn’t read, Tubman explained later. She was simply trying to throw him off, and it worked.

All of these tricks and more put Tubman in a position later in life to make her famous boast that “I never ran my train off the track and I never lost a passenger.” That boast was well-earned, of course, but Tubman was also the sort of person who was quick to thank her “Guardian” for helping her through all of those close calls. Here, again, is Bradford, quoting Tubman herself:

I tell you, Missus, ’twan’t me, ’twas de Lord! Jes’ so long as he wanted to use me, he would take keer of me.… I always tole him, I’m gwine to hole stiddy onto you, an’ you’ve got to see me trou.

POSTSCRIPT: On Conductors Getting Paid

As chairman of the Vigilance Committee of the Pennsylvania Anti-Slavery Society, William Still served as a primary gatekeeper welcoming runaway slaves as they crossed the border into Pennsylvania and sought help making it on to points north and across to Canada.

Still kept a detailed “Record of Facts, Authentic Narrative, Letters, &C.” that he published in 1871 under the title, The Underground Railroad. Here is what he had to say on questions that arose surrounding one conductor who charged fees for his services.

[A] captain by the name of B., who owned a schooner, and would bring any kind of freight that would pay the most, was the conductor in this instance. Quite a number of passengers at different times availed themselves of his accommodations and thus succeeded in reaching Canada.

His risk was very great. On this account he claimed, as did certain others, that it was no more than fair to charge for his services—indeed he did not profess to bring persons for nothing, except in rare instances.

In this matter the Committee did not feel disposed to interfere directly in any way, further than to suggest that whatever understanding was agreed upon by the parties themselves should be faithfully adhered to. Many slaves in cities could raise, “by hook or by crook,” fifty or one hundred dollars to pay for a passage, providing they could find one who was willing to risk aiding them. Thus, while the Vigilance Committee of Philadelphia … neither charged nor accepted anything for their services, it was not to be expected that any of the Southern agents could afford to do likewise.

This is excerpted from Tubman Travels: 32 Underground Railroad Journeys on Delmarva. Learn more about the book, including where to buy a copy, here.

–written by Jim Duffy; posted on July 20, 2018

–Copyright 2018 Secrets of the Eastern Shore/Whimbrel Creations LLC. All rights reserved.

NOTES: Travel Info & Resources

(1) In addition to its Tubman materials, the Seaford Museum has a display about the notorious slave kidnapper and murderer Patty Cannon. Check with the museum in advance for current seasonal hours before visiting. The museum is located at 203 High Street, Seaford, Delaware.

SeafordHistoricalSociety.org; Facebook.com/SeafordDEHistory; 302.628.9828

(2) Information about things to do and places to go in and around Seaford is available from Southern Delaware Tourism.

VisitSouthernDelaware.com; Facebook.com/SouthernDelawareTourism; 800.357.1818

(3) The Harriet Tubman Underground Railroad Byway runs through both Dorchester and Caroline counties in Maryland and then on into Delaware.

• Maryland: HarrietTubmanByway.org; Facebook.com/HarrietTubmanByway; 410.228.1000

• Delaware: TubmanBywayDelaware.org

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