Drawn from MHS collections, our primary source sets promote learning in U.S. history and civics and are supported by teaching activities and guiding questions.


Portraits of Enslavement and Freedom

Inquiry Question: What can portraits tell us about the past?

Portraits are primary sources that tell us about the people who appeared in and painted them. In this set, you will look closely at three portraits to see what they show us about the lives of Black people in colonial and revolutionary Massachusetts. What can we learn about individuals? What information remains hidden?

    Source Set

    Download Source Set


    Enslaver: someone who bought and owned other people as their property

    Merchant: someone who buys and sells goods, and imports those goods from other countries

    Negotiate: to come to an agreement with someone by talking with them


    Looking at Images

    While you look, ask yourself:

    What do you notice?

    What do you think you know about the person, or people, in the image?

    Who might have seen this image?

    • Do you think it was made to be seen publicly, or privately?

    What do you wonder?

    Take notes here

    Samuel Shrimpton was a wealthy Boston merchant who owned slaves. Slavery was common and legal in Massachusetts until the 1780s. This portrait was painted in 1675.

    Located in the background is the first known image of an enslaved person in New England. Click on the image and zoom in to see the painting in more detail.


    Citation: Samuel Shrimpton, Oil on canvas by an unidentified artist of the British school, 1675, Massachusetts Historical Society, https://www.masshist.org/database/6070.

    Phillis Wheatley was a poet. She was the first Black woman to have her work published in the American colonies. Born in the Senegambia region of west Africa, she was kidnapped from her home when she was around seven or eight-years-old and the wealthy Wheatley family bought and enslaved her in Boston. 

    Wheatley learned English and how to read and write while she was enslaved. After publishing her first book of poems in London, she negotiated her freedom. This image appeared in the front of her poetry book. The engraving was done by Scipio Moorhead, a Black man who was enslaved in Marblehead, MA by Reverend John Moorhead.

    You can compare this lithograph, with Wheatley's signature at the bottom, to the original engraving that appears in her 1773 book, Poems on Various Subjects, Religious and Moral. She was about 19 or 20-years-old at the time the engraving was made.

    Citation: Phillis Wheatley, Lithograph by Pendleton, Massachusetts Historical Society, https://www.masshist.org/database/1760.

    Elizabeth Freeman was born into slavery in New York. When her enslaver’s daughter married a Massachusetts man, Freeman was forced to go with her to Stockbridge, Massachusetts. Freeman could not read or write, but in 1780 she got a lawyer and used the Massachusetts courts to sue for her freedom. In freedom, she worked as a housekeeper and bought a home where she lived with her children and grandchildren.

    Freeman was about 67-years-old at the time this portrait was painted. Susan Anne Livingston Ridley Sedgwick painted this miniature watercolor portrait in 1811. Sedgwick was related to Freeman’s lawyer, Theodore Sedgwick. Freeman also worked for Theodore Sedgwick's family as a free woman.

    You can see the gold beads she wears as a necklace in the portrait here.

    Citation: Elizabeth Freeman ("Mumbet") Miniature portrait, watercolor on ivory by Susan Anne Livingston Ridley Sedgwick, 1811, Massachusetts Historical Society, https://www.masshist.org/database/23.
    For Teachers

    Explain to students that historians interpret items–like paintings–made in the past to see what they can tell us about the people who lived then, the places they lived, and even big institutions, like slavery, that were happening at the time they lived.

    Before we can interpret something, we need to look closely at it and ask questions about it. Sometimes we don’t have all of the information we need, so we use context clues to help us make hypotheses, like scientists do. Sometimes, we have questions that cannot be answered. Then, we can try to find more sources that help us answer them. We can also think about why those questions can’t be answered. (Often, that tells us about power structures!)

    Inquiry Questions

    After students have had an opportunity to examine the portraits and take notes on the Google slides, you can dig deeper to help them further analyze the images and make meaning out of them.

    Source 1: Samuel Shrimpton, Enslaver
    • What does each person’s location in the portrait tell you?

    • What role might the enslaved person have had in Shrimpton’s household/business? Do you think the Black person got to choose what to wear for the portrait?

    • Do you think it was his choice to appear in the portrait at all? Shrimpton paid for this portrait to be painted.

    • Why do you think Shrimpton wanted this person included in the portrait?

    • What information does this painting (including caption) not give about the person in the background? Why might that be left out?

    • What does the inclusion of an enslaved person in the portrait of a well-known, wealthy Bostonian tell you about slavery in MA in 1675?

    Source 2: Phillis Wheatley

    Students can compare the image as it was printed in 1834 with the original engraving as it appeared in her 1773 book.

    • How does Wheatley choose to portray herself? What objects are included in the image?

    • What can you learn–or hypothesize–about her from this image?

    • Where is she looking?

    • What do you think she might be thinking about? (Historians don’t always know all of the answers, but we try to use context clues to make educated guesses!) Why might we be seeing Wheatley from the side?

    • What do you think was important to Wheatley?

    Source 3: Elizabeth Freeman

    During her lifetime and in many sources written about her, Freeman was and is frequently referred to as "Mumbet." 'Bet' was short for "Betty," a nickname for Elizabeth. "Mum" was a reference to her role as a nanny for the Sedgwick children. However, when she gained her freedom, she chose "Freeman" as her legal last name. We do not know what Freeman's own family (including her children, grandchildren, and great grandchildren) and friends called her. In this set, we choose to use the legal name Freeman chose for herself.

    • How does Freeman choose to portray herself? 

      • What details stand out to you?

    • What can you learn about Freeman from the portrait of her?
    • The painter was related to Theodore Sedgwick, Freeman’s lawyer and employer. Who might this miniature (very small) portrait have been for?


    Suggested Activities

    Visual Teaching Strategy

    Project one image at a time. For each:

    Ask students to look at the image silently for 1-2 minutes.

    • Then, ask, “What is going on here?” 

    • Summarize student responses in an open-ended manner (“this friend thinks it could be…”) 

    • Follow-up: “What do you see that makes you say that?” (This helps students cite evidence in the image for their assertions.)

    • Continue the conversation: “What more can we find?” Compare and contrast different things students say.

    • At the end of the conversation, read the source description with the students. What can they learn from it?



    Creating self-portraits

    In this activity, students will draw self-portraits, which gives them an opportunity to choose how to portray themselves to other people. 

    • Ask students, "If historians look at your self-portrait in 100 years, what will they be able to learn about you? About the 21st century?"

    Some questions students may want to consider:

    • What materials will you use (e.g., pencil, markers, paints)?
    • What will you wear?
    • Where will this image be displayed?
      • Who will see it? 
    • Will anyone else appear in the image with you?
    • Will you be doing an activity? Will you have any props in the image?
    • What will the background be?
    • Will you put a frame around the image? 
    • Will your portrait have any words? If so, what will they say?


    Applicable Standards

    MA HSS 2018 Framework

    Content Standards

    Grade 3, Topic 5, The Puritans, The Massachusetts Bay Colony, Native Peoples, and Africans

    Grade 5, Topic 5, Slavery, the legacy of the Civil War and the struggle for civil rights for all

    Practice Standards

    Develop focused questions or problem statements and conduct inquiries

    Analyze the purpose and point of view of each source; distinguish opinion from fact

    C3 Framework

    D2.His.6.3-5. Describe how people’s perspectives shaped the historical sources they created.

    D2.His.13.3-5. Use information about a historical source, including the maker, date, place of origin, intended audience, and purpose to judge the extent to which the source is useful for studying a particular topic.


    Additional Resources

    Additional Materials at the MHS

    Additional Primary Sources: Portraits and Miniature Portraits

    The MHS holds many more digitized portraits from the time periods included in this source set. You may want to have students compare and contrast portraits of these wealthy white men, women, and young people to the portraits in the source set.

    Mrs. Baker, 1675

    This image of a married woman was painted in London in 1675. The clothing she wears and props she holds and sits beside give us clues about her middle-class status.

    Increase Mather, 1688

    John van der Spriett's portrait of Increase Mather depicts the Puritan minister in his library. Mather was associated with the Salem witch trials of 1692-1693. Mather largely defended the trials in his writings and sermons, but he warned against the use of "spectral evidence," a type of evidence presented in a trial by someone who claims to have experienced visions (of witchcraft).

    Dorothy Quincy, 1720

    Created around 1720, this painting depicts Dorothy Quincy of Braintree, Massachusetts when she was somewhere between 10 and 13 years old. It is one of the earliest (surviving) portraits of a child in New England. A glimpse of Boston’s urban architecture and three hills (Trimount or Tremont) can be seen in the background. The color of her dress is unusual for this period; most people were red or blue because green dye faded easily and was thus a more expensive choice. Along with the silken shawl, Dorothy's green dress is a symbol of her family's wealth. The parrot locates the picture in North America, and would have been very exotic, or unusual, to people back in England.

    Hannah Gookin Tracy, circa 1749-1752

    Painted shortly after her marriage, when she was about 25-28 years old, Hannah holds a garland of flowers and poses in front of an outdoor landscape.

    John Hancock, circa 1770-1772

    John Singleton Copley, Boston's most respected portrait painter in the 18th century, painted this portrait of John Hancock during the years leading up to the American Revolution. Hancock was a wealthy merchant, but after the British seized goods from one of his ships in 1768 some colonists viewed him as a patriotic victim of English oppression.

    Elizabeth Oliver Lyde, 1811

    Lyde is about 73 or 74 years old in this miniature portrait. 

    Jane Winthrop, 1819

    In miniature portrait, Winthrop, a young woman is turned toward the side in profile. In the corner, we can see sheet music and a piano. In the early 1800s, painting miniature portraits was more open to women than other types of art. The artist of this miniature was Sarah Goodridge. A woman artist also painted Elizabeth Freeman's 1811 miniature portrait.

    Unidentified Woman, 1800s

    This portrait appears to be from the Victorian Era in the mid-1800s. It has quite an elaborate frame that is shaped like a lyre (an ancient stringed instrument) and set with fake stones.

    Secondary Source: MHS Podcast Episodes

    The MHS podcast, The Object of History, has an episode on Elizabeth Freeman and one on Phillis Wheatley.




    Questions or suggestions? Contact us at education@masshist.org.