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Lessons in Looking: Contraband in Paintings

In this activity students analyze Theodor Kaufmann's 1867 painting On to Liberty. Students practice finding information and making inferences based on the painting by completing a graphic organizer. Then students read a descriptive paragraph of the painting, noting where the author has cited information from the painting and where the author has made inferences and drawn conclusions. Then students analyze another painting of a similar theme, Eastman Johnson's A Ride for Liberty. The activity concludes by asking students to synthesize what they have learned about the Civil War based on the painting. The activity may make a good culminating lesson about the Civil War or an introductory lesson on Reconstruction.


  • Students will analyze paintings to determine what the Civil War meant for freedpeople.  

  • Students will practice finding information and making inferences from visual sources.  


Step 1: Project or display Theodor Kaufmann's painting On to Liberty. Pass out copies of the worksheet/graphic organizer. Ask students to spend a few minutes examining the painting and completing COLUMN A of the worksheet. The teacher may choose to tell students when it was created (1867) or to share details from the description of the painting, but the teacher may elect to let students have minimal information before making their hypotheses. 

Step 2: After students have had time to list 10 items and make some hypotheses about what is going on, ask students to share out responses. As students describe what they see, either the student or the teacher should point to the area in the painting under discussion. As students tell their hypotheses, they should point to the details in the painting that informed their ideas. Before moving on to the next step, review with students what information/facts they have gleaned from the painting and what inferences they have made. 

Step 3: Pass out the handout with the two paragraphs. Tell students that they are going to read the same paragraph twice, once where the information is in bold and once where the inferences and conclusions are italicized. Read aloud or ask for student volunteers to read aloud to the class. As new details are described in the paragraph, point them out to the whole class (red beads, shadows, army encampment, etc.).

Step 4: Ask students to return to their worksheets and complete COLUMN B. Then ask students to share their additional insights. (Optional: pass out Background Essay on Contraband and read aloud. Ask students to share what new insights about contraband and the painting they gain from the reading.) 

Step 5: Tell students that they will now look closely at a different painting of a similar theme. Project and pass out Eastman Johnson’s A Ride for Liberty. Facilitate guided looking, comparing to On to Liberty. Discuss:

  • What do these two paintings teach us about the Civil War? 

Step 6: (Optional) Have students respond to the discussion question above in a short essay. Students should use evidence cited in their graphic organizer to support their answers. 


Historical Context

As the Union Army progressed through the South during the Civil War, former slaves became free men and women. Rather than wait for the slow-advancing military, hundreds of thousands of slaves decided to take matters into their hands by fleeing to Union lines. Known as contrabands, the former slaves often helped the army scout unknown territory, build roads and set up and break down camps. In some areas, notably the coastal islands off the coasts of Georgia and South Carolina and the rich cotton belt of northern Louisiana and Mississippi, Union officers distributed confiscated plantation lands to the former slaves who had worked them. 

At the end of the Civil War, the future of newly emancipated freedpeople was uncertain. Congress had passed the 13th Amendment banning slavery, but had not yet passed laws protecting the civil rights of former slaves. African Americans and many white Northerners, particularly Radical Republicans, felt that black people had more than earned their right to citizenship, proving themselves worthy by their service in the Union Army. Also at issue remained the question of land: would former slaves be entitled to any of the land they had toiled on for so long? All of these questions swirled in the air during the early months of Reconstruction in 1865.  

Source | American Social History Project/Center for Media and Learning, 2010.
Creator | American Social History Project/Center for Media and Learning
Rights | Copyright American Social History Project/Center for Media and Learning This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License.
Item Type | Teaching Activity
Cite This document | American Social History Project/Center for Media and Learning, “Lessons in Looking: Contraband in Paintings,” SHEC: Resources for Teachers, accessed September 22, 2023,

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