Reaching Between the Lines

An art contest helps students imagine the lives of runaway slaves

By Thom Thacker, Michael A. Lord

Illustrator: Caroline Torres

Illustration: Caroline Torres
Above, the winner of the “Pretends to Be Free” art contest.
‘Bound’ by Caroline Torres
The runaway slave, Violet, is trying to escape and her owner is trying to catch her. To show this, I used different colored charcoals and drew Violet running away. The white bondage around her, dragging her down, represents the slave owners and everyone else trying to capture her and force her back into slavery. The background is a nighttime scene far away from where Violet ran from. But even though she is so close to freedom, she is soon captured, bound, and brought back to slavery by her white slave owner, like so many before and after her.

200 Dollars Reward. Was stolen by her mother, a Negro Girl about 9 or 10 years old, named Dianah — Her mother’s name is Cash.
— New Jersey Gazzette, April 23, 1778

WENT off from his master on Thursday night, a Negro Wench, called VIOLET, with her male children, one about 7 years old, called Willis, the other about 2 years old, named Joe. The Wench is about 26 years old, tall, thin, and somewhat pitted with the small-pox. The youngest boy is rather of a yellow complection. Both boys have lately had their hair or wooll cut short. Whoever apprehends said Negroes, and brings them to the Subscriber’s House, at Green-wich, shall have a reward of Five Guineas immediately paid them.
— The Royal Gazette (New York)
May 24, 1783

“Offensive,” “inhumane,” “absurd” were a few of the comments expressed by high school students after they read advertisements like the one above. The students, from two schools in the Lower Hudson Valley region of New York State, examined the ads for runaways in preparation for an art contest sponsored by Philipsburg Manor, a historic site in New York’s Hudson Valley.

Philipsburg Manor, where we both work, was once owned by a family of Anglo-Dutch merchants and operated by a community of 23 enslaved Africans. The central mission of Philipsburg Manor is to bring to light this hidden history of slavery in the North. During the colonial period, advertisements like the one excerpted above were a common sight in many newspapers. Today, these primary documents can serve as painful reminders of our nation’s history. They also can help us discover new perspectives on our past.

In the fall of 2005, Philipsburg Manor created an art contest we titled “Pretends to Be Free: Imagining Runaway Slaves.” We initially targeted eight local high schools for participation in the contest, but surprisingly, only two chose to participate. After doing some development work with mentor teachers, students produced artwork based on the ads. In addition to submitting a piece of two-dimensional art in any medium, the contest required students to submit commentary describing their work and the reasons they chose particular advertisements.

We also required the teachers to have the participating students read an essay we crafted about biases in advertisements for runaways. The essay was drawn largely from the book “Pretends to Be Free:” Runaway Slave Advertisements from Colonial and Revolutionary New York and New Jersey. We wanted to be sure that students understood that runaway advertisements were written by slave owners and written for people in support of slavery. The advertisements refer to women as “wenches,” men as “boys,” and hair as “wooll.” They also list character traits like “deceitful,” “cunning,” “slow-witted,” and “clumsy.” These de-scriptions give more insight into the authors than the true nature of the individuals who ran away. While a significant resource, runaway notices must be read with an understanding that these are painful reminders of an era marked by grave inhumanity. Documents written by slave owners about their slaves tell only one side of the story.

We chose to use runaway advertisements from local newspapers to draw attention to the scope of colonial enslavement in the North. It is a little-known fact that in 1750 slavery was legal in all the northern colonies. In New York City, for example, about 20 percent of the population was enslaved, making it the second largest slave-holding city in all the colonies. The hundreds of advertisements for runaways printed in New York newspapers provide a wealth of knowledge about enslaved individuals and their communities. In addition to some physical description, the ads provide a glimpse into the personalities and motives of those who chose to run. And the acts described in the advertisements are evidence of ongoing, determined resistance by individuals against the institution of slavery.

Designing the Contest

Initially, the idea for using such potentially loaded advertisements for an art contest met some resistance from Philipsburg Manor’s African American Advisory Board, a community board whose insight and input has been essential to program development at the museum. One member voiced strong concerns about the kind of work that might be created. She feared that students who did not take the contest seriously might submit images that desecrated the memory of the individuals described in the ads. With the board’s concerns in mind, we designed the contest logistics so that Philipsburg Manor staff would work closely with the schools and teachers involved. The contest guidelines stipulated that students identify a mentor teacher with whom they would discuss the essay and the ads.

The mentor would also offer guidance during the creative process. These safeguards prevented the submission of any thoughtless or intentionally offensive pieces of work.

After attempting to reach out to teachers at eight high schools, Philips-burg Manor was able to identify two teachers at area high schools who were eager to participate. Ann deMartin is an art teacher at Ossining High School, a 1,250-student high school with a diverse student body (43 percent white, 35 percent Hispanic, 17 percent African-American, and 6 percent American Indian/Asian). Brett Bowden is a history teacher from the 470-student Croton-Harmon High School. The high school is more than 90 percent white and draws from diverse socioeconomic groups.

Both teachers understood this project’s potential to integrate the disciplines of art, history, and English in a manner that would have meaning and relevance for the students. Bowden introduced the contest at the tail end of a classroom simulation about slavery. Bowden says his students “had given considerable thought to slavery, which they considered to be a southern phenomenon.” He says the project helped his students understand the notion that slavery was a northern issue as well. Bowden coordinated his efforts with two art teachers and distributed materials to any student he thought might be interested in art. After initial discussions, the students worked mainly on their own, with Bowden offering support as needed. The resulting artwork “blew me away,” Bowden says.

DeMartin took a slightly different approach. As an art teacher, her goal was to have students’ “drawings gain strength in message, media, and creativity.” She took her students to an exhibition of artist Jim Dine, a contemporary artist known in part for his expressive interpretation of images, at a local museum, hoping to show “the power of color, contrast, and scale to create dynamic effects on the page.” DeMartin read the advertisements aloud to her students and discussed the images that came to mind. Because this was one of the central projects for the term in her class, she provided constructive feedback and guidance to the students throughout the term.

Thirty-eight students participated in the contest, which carried a $1,000 scholarship for first place, a $500 scholarship for second place, and a $100 gift certificate for art supplies for third place. The caliber of the work and the thoughtful and emotional statements that accompanied the pieces submitted suggest that the process of creating their artwork helped students develop empathy for the individuals described in the advertisements.

One student wrote, “The ad that particularly struck me was the one proclaiming the theft of a nine-year-old daughter by her mother. This struck me as absurd — the fact that a mother could ever be charged with stealing her own daughter.” Another student, who based his work on an advertisement for an enslaved individual who cleverly staged his own drowning, wrote that he found the runaway’s “tactics admirable because they were a clear contradiction of the commonly thought notion of the time period that slaves were not smart.” A third student revealed that when she “found out that slavery was widely used in the North, even in Westchester [County], I was surprised.”

Jerry and Gloria Pinkney, nationally renowned, award-winning children’s book artists and illustrators, helped judge the artworks. Mr. Pinkney remarked that he was deeply moved by the students’ artwork and their “articulate expression of something that they did not live through and the clarity with which they tried to express this difficult and horrendous time.” Ms. Pinkney added that the artworks have great relevance today because “people are still enslaved around the world. Hopefully, shows like this depicting how horrific slavery was and is will encourage people to struggle to end it once and for all.”

Runaway slave advertisements can provide teachers and students with a significant primary source for understanding the cultures, skills, languages, and appearances of enslaved people as well as providing evidence of the ongoing defiance of the enslaved community. They can also help students understand the inherent — and in this case, obvious — biases of primary documents. Using art and writing to respond to the history of slavery provides teachers with an opportunity to give students a new and powerful way to develop empathy with individuals from centuries ago. As a result, the classroom can be transformed into a place where high school students can develop connections between significant historical issues and events and their own passions and interests.n


“Pretends to Be Free: Imagining Runaway Slaves” online exhibition. Includes 25 artworks, statements, an essay, eight runaway advertisements, and classroom activities.

“The Enslaved African Experience in the Colonial North and at Philipsburg Manor” online exhibition. Includes essays and other educational materials about slavery in the colonial north.

“Pretends to Be Free:” Runaway Slave Advertisements from Colonial and Revolutionary New York and New Jersey (Garland Publishing, 1994).

Thom Thacker ( is site director and Michael A. Lord ( is site manager at Philipsburg Manor in Sleepy Hollow, N.Y. Philipsburg Manor is one of a network of six sites owned or operated by Historic Hudson Valley. Support for “Pretends to Be Free” was provided, in part, by the Puffin Foundation, the Allan M. Block Agency Inc., and the Rotary Club of the Tarrytowns.