In 1771, Berkshire County property tax records show there were:
• 19 enslaved humans of African descent in Sheffield;
• 7 enslaved humans of African descent in Stockbridge;
• 3 enslaved humans of African descent in Egremont.
People were enslaved in the southern Berkshires, living out their lives as human chattel, since at least the 1740s. Further north as well—a surviving bill of sale records the 1761 purchase of “a negro girl named Pendar” for £50 by Col. Williams of Pittsfield. That there weren’t far more slaves was a matter of simple economics: the area was generally poor and markets too far to bother ramping up surplus farm production.

But Connecticut was closer to larger population centers and held more enslaved peoples. In 1779, the Connecticut Courant (predecessor of today’s Hartford Courant) ran the following advert for a paying subscriber and slaveowner in Sharon, Connecticut:
“TWENTY DOLLARS REWARD. Runaway from the subscriber in October last, a Negro Wench named ZIL, about 15 years old, small of her age, pretends she is free, the last she has been heard of she was going to Lenox. Whoever will return her to her master shall receive the above reward . . . .”
Such ads were commonplace.
Connecticut was the last colony in New England to abolish slavery in 1848 and at times had more enslaved men and women than any other state in New England. Runaway slaves from Connecticut and New York State (which didn’t vote to abolish slavery until 1817) frequently headed for the Berkshires, where slavery existed alongside free Blacks. That’s right—enslaved Blacks and free Blacks lived parallel lives in the Berkshires. Little Zil “pretended to be free” because some Blacks here were.
Given that the county borders Connecticut and New York, the Berkshires were something of a temporary melting pot. Walking down Main Street in Stockbridge one might encounter enslaved Blacks, free Blacks, Dutch and English landowners, Mohawks and Mohicans, speaking a polyglot of languages.
The story of being Black in the Berkshires is largely untold. It’s a legacy of injustices endured, freedom attained, of human hatred and human kindness, of lasting yet dissipating segregation, of limited economic opportunity, of one people and two races, living in parallel, separated by little more than ignorance and legacy. Two ships silently passing in the night.
It’s the story of a White race burdened by prejudice; a Black race anything but ignorant of its white neighbors, often working in their homes as domestics, washing their dirty linens and underwear, cooking their meals, and raising their children, first as chattel, later as waged labor. As W.E.B. Du Bois wrote, “We who are dark can see America in a way that white Americans cannot.”
If you’re white, chances are you don’t know a lot about this history. As Wray Gunn, an elder in the local Black community with deep local roots here that date back to the American Revolution, says: “The Berkshires are rich in Black history that is little known and sometimes misunderstood.”

It’s a history peopled by giants the likes of W.E.B. Du Bois (or “Willie” as he was known locally; last name pronounced in the American way), a towering international figure and pioneer in the field of Sociology and the American Civil Rights movement. And Mum Bett, who threw off the shackles of human enslavement with a bravery and chutzpah almost biblical in proportion and renamed herself with a moniker monumental in its clarity, a name with a significance that would never tarnish as it rang through the ages: Elizabeth Freeman.
Sprinkled among these leviathans of our shared cultural history are a fascinating amalgamation of artists, patriots, and the everyday amongst us, who rose above the petty slights and substantial impediments underwritten by institutional racism.
Agrippa Hull, he of quick wit and talented business acumen, born of slavery in Northampton, who served as orderly to military engineer Gen. Tadeusz Kosciuszko during the Revolutionary War and became the largest Black landowner in Stockbridge.
The Rev. Samuel Harrison, born enslaved, who would become a highly regarded minister of the Second Congregational Church in Pittsfield and chaplain to the 54th Massachusetts Regiment which was celebrated in the Oscar-winning movie Glory.
James Weldon Johnson who wrote the Black National Anthem while summering at this home in Great Barrington. James VanDerZee, who grew up in Lenox and became famous as the chronicler through his photographs of the Harlem Renaissance.
And the sympathetic whites. The Sedgwicks of Stockbridge who helped free and then employ Ms. Freeman. Norman Rockwell, who refused the complicity of silence and used his prodigious talents to portray human decency and profanity, using local Black children as models for several of his most powerful works. Jacob’s Pillow, which incorporated Black dance troupes and choreography from its earliest beginnings.
Much of this story, while enjoying a renaissance of interest, is physically missing. In Berkshire County, Black people weren’t generally a prosperous lot. Many of the landmarks associated with their history are no longer existing, many of them literally paved over. But if you drive through the county with a healthy dose of curiosity, the history remains for those willing to find it.
Elizabeth “Mum Bett” Freeman
Any time while I was a slave, if one minute’s freedom had been offered to me and I had been told I must die at the end of that minute, I would have taken it—just to stand one minute of God’s earth a free woman, I would. —Elizabeth Freeman

It’s uncomfortable to imagine the indignities of being enslaved, the fear of bodily harm and sexual violence with no recourse, an existence as chattel, human property devoid of dignity and self-determination, expected to deliver a lifetime of uncompensated involuntary labor, prisoner to the whims and brutality of one’s legal owner. In such a world, it’s difficult to imagine the bravery of one who stands up against impossible odds to say, “No more!” Rosa Parks on that Montgomery public bus comes to mind. But there’s an earlier example of such bravery, one against even greater odds, and at a time when deliverance was hardly imaginable.
It is the story of Bett, enslaved in the home of Col. John Ashley in Sheffield since she was six months old. Perhaps it was, as recorded, the enduring of a painful blow from a hot oven shovel from Ashley’s violently tempered wife, Hannah, that finally pushed Bett over the edge. She marched into the winter night from Ashely Falls to Sheffield, where she visited the home of noted attorney and future Massachusetts Supreme Court justice, Theodore Sedgwick, to ask for her freedom. Bett had heard Col. Ashley and his male friends discussing the new state constitution, with its proclamations of equality. Sedgwick agreed and tried Bett’s case for freedom in the local courthouse in Great Barrington. Bett won her freedom in August of 1781 and inhaled her first breath of freedom right here in South County. She took the name Elizabeth Freeman, and spent her remaining days employed by the Sedgwicks, who soon moved to Stockbridge.

Ms. Freeman is buried directly alongside other members of the Sedgwick family in the “Sedgwick Pie”—the family’s historically significant circular burial plot in the Stockbridge cemetery. Her gravestone reads, “She was born a slave and remained a slave for nearly thirty years . . . . She was the most efficient helper and the tenderest friend. Good mother, farewell.”

Visit the Col. John Ashley House. The small grounds in Ashley Falls are open year-round. Although the home is closed in winter, a visitor can still consider Ashley’s slaves sleeping in unheated outbuildings and on the kitchen floor near the fireplace during the coldest months. Driving north through Sheffield, you can see the old Sedgwick white-pillared home on Main Street (privately owned) to your right in the center of town. The courthouse where Ms. Freeman earned her freedom is now gone, in its place another public edifice of note: the Great Barrington Town Hall. The Sedgwick home on Main Street in Stockbridge is privately owned, but the cemetery is open to the public and the Sedgwick Pie is definitely worth a visit. (The grave of Agrippa Hull is also in the cemetery.) And consider visiting the Elizabeth Freeman Centerwebsite, reading about the good work that they do in our community—and possibly contributing.
W.E.B. Du Bois
I was born by a golden river in the shadow of two great hills, five years after the Emancipation Proclamation. —W.E.B. Du Bois
Du Bois was born right downtown on Church Street. He went to school at the old Great Barrington High School that stood behind the present Berkshire Co-op Market. Great Barrington is where he chose to bury his infant son, and then his wife of four decades, as well as his daughter. It’s where the local Congregational Church along with three other churches, encouraged by Du Bois’ schoolteacher, sent this unusually bright yet impoverished native son to college at the historically black Fisk College. Du Bois would continue on to Harvard, where he became the first African American to earn a Ph.D.
Great Barrington is also where Du Bois encountered his first slight as a Black man, during a high school Valentine’s Day fundraiser. Du Bois frequently wrote about his birthplace with a sense of longing. One could wonder if he regretted moving to Ghana at the age of 93, only to die there less than two years later, buried in African soil, yes, but not beside his wife and children in the soil of his beloved Great Barrington.
If you haven’t read Du Bois’s writings, please do. When it comes to America and race, they’re tectonic in their significance. “The problem of the 20th century is the color line,” he wrote in The Souls of Black Folk in 1903, the same year that Sheffield established what was widely seen as a Jim Crow segregated school. And he had this to say as well: “The United States will either destroy ignorance, or ignorance will destroy the United States.” Potent stuff. If you’re new to Du Bois’ writings, consider following along in a community read of The Souls of Black Folk with the help of renowned Du Bois experts from around the country. It’s awesome.

The celebration of Du Bois’s legacy in Great Barrington—despite his being the most significant son of the Berkshires and having been nationally honored on two postage stamps—has been strangely complicated. Although his homesite on the edge of town was declared a National Historical Site in 1976, it took thirty more begrudging years for local residents to honor him with road signs announcing Great Barrington as his birthplace. It took another two decades and several attempts to get a public school named for him. No, it didn’t help that he was a Black man in a racist society. It also didn’t help that he became an avowed communist in his final years. And yet, given the experience of American Blacks during his lifetime, one might find this late conversion understandable from a place of frustration.

While Du Bois’s words live on, breathing with a clarion urgency as loud as the day he wrote them, his physical legacy in Great Barrington is mostly gone, much of it literally paved over. None of the five homes he lived in in Great Barrington survives. One is now the parking lot at the top of Railroad Street, another is beneath Taconic Avenue. A third is a green lawn on Church Street, a fourth the parking lot beside First Congregational Church. To feel Du Bois’s presence, one has to dig a little deeper. Visit the Mahaiwe Cemetery south of town on Route 7. There, you will find a Great Barrington Historical Society marker beside the graves of his wife, and two children. Call the North Star Bookstore right next door and make an appointment to explore the Du Bois Center within. Run by Du Bois expert and bookstore owner Randy Weinstein, the center is a treasure trove of Du Bois writing and more. Turn down Route 23 and drive towards South Egremont. Just past the Route 71 turnoff for the airport, you will see a parking lot on the right beside a grove of pine trees. This is the Boyhood Homesite of W.E.B. Du Bois, a National Historic Site maintained by the University of Massachusetts Amherst. Now devoid of structures save for remnants of the foundation of his family home (the house adjacent to the parking lot is not the homesite), there is however a short trail through the woods with interpretive signs explaining Du Bois’s legacy.

In downtown Great Barrington, check out the colorful and poignant Du Bois murals in the wide alleyway between Railroad Street and the Triplex parking lot, painted by the Railroad Street Youth Project. Walk down Church Street and check out the sign marking where Du Bois was born. And the River Garden dedicated to Du Bois at the River Walk, where the street meets the Housatonic River. Du Bois wrote frequently about the river and the need to protect it from further degradation.
Clinton A.M.E. Zion Church
For 130 years, this church on Elm Court one block from Main Street served as a “spiritual, cultural, and political heart of Black life” in the southern Berkshires. The restoration project, which will turn the church into a cultural center dedicated to educating the public about the life and legacy of W.E.B. Du Bois and the Berkshires’ rich African American history, needs your help. Please check out its website and consider contributing. The church renovation is very much incomplete, but you can pay your respects from outside and stroll around this historically Black neighborhood.

James Weldon Johnson
Johnson, a novelist, poet, songwriter, and Civil Rights activist, is best known for writing “Lift Every Voice and Sing”—also known as the Black National Anthem. He was a frequent patron of the Great Barrington Public Library. He summered for years at a summer home called Five Acres in Great Barrington, now private property, and his writing cabin, still there, will be restored by the James Weldon Johnson Foundation which has also joined with Bard College at Simon’s Rock to support an annual artists-in-residence program.
Stockbridge
In addition to the Sedgwick Pie, the Stockbridge Cemetery is the final resting place of Agrippa Hull, a free Black who fought in the Revolutionary War. His portrait also hangs in the Stockbridge Library. You might also consider visiting a little-known monument to the Mohican Indians who once lived in Stockbridge before being displaced. You can find it on the left just outside town as you drive west down Main Street towards the golf course.

The Norman Rockwell Museum houses many of the artist’s Civil Rights-era drawings and paintings. Rockwell, who was a sponsor of the original Du Bois Memorial Committee, used local Black children as models for his seminal magazine covers “The Problem We All Live With” and “Moving Day”.
Lee
The 54th Massachusetts Regiment, all Black except for white officers, fought bravely for freedom, as chronicled in the movie Glory. What is not typically known is that more Black men from the Berkshires volunteered to serve in the regiment than from anywhere else in the Commonwealth. A plaque on Lee’s Memorial Hall pays homage to several who served, never to see their families nor the beauty of the Berkshires again.
Lenox
The town’s most famous Black son is James VanDerZee, who received white recognition late in life for his seminal photographs of the Harlem Renaissance. His work gained international recognition in 1969, when it was included in an exhibit at the Metropolitan Museum of Art titled “Harlem on My Mind.” His photos have been exhibited locally by the Lenox Historical Society and the Lenox Public Library. His boyhood home was taken by eminent domain to build the Route 7 bypass around Lenox. Every time you drive towards Pittsfield and past Hubbard Lane about a mile south of the Lenox Commons shopping area, you’re driving through where his boyhood home once stood.
Pittsfield
The Samuel Harrison House in Pittsfield was the home of Reverend Harrison, who served as chaplain to the Massachusetts 54th Regiment. Beautifully renovated as a community project just a decade ago, it’s open to the public by appointment.
Dalton
The Hoose House, which had a succession of Black owners, and nearby Wizard’s Glen, reputed to be a stop on the Underground Railroad, provide an interesting window on African American life in Berkshire County.
History, as we know, is often found in books. If you want to know what it was like to be Black in the Berkshires one hundred years after the Civil War, you’ll find poignant tellings in African American Heritage in the Upper Housatonic Valley (a highly recommended read). In one essay, “Life in the Invisible Community”, the late Elaine Gunn, a longtime local schoolteacher, writes about trying to purchase a home in Great Barrington and the blatant racism she faced while doing so.
She also wrote the following about dining in mid-20th-century Pittsfield: “One restaurant had two doors . . . . Blacks always went in on the left and were seated on the left. A solid wall separated the two dining areas. The right side of the restaurant . . . all the tables had reserved signs on them.”
For more information, please visit the following websites:
Local Black history:
https://www.africanamericantrail.org/plan-your-trip/trail-guides/
https://www.africanamericantrail.org
https://housatonicheritage.org/heritage-programs/afam-trail/
The Du Bois Center at UMASS Amherst:
http://duboiscenter.library.umass.edu/about-du-bois-library/