Learn About Black History in the Berkshires

The Upper Housatonic Valley African American Trail

By Taylor Staubach, Publisher, Berkshires Macaroni Kid February 1, 2023

Black History in the Berkshires is best learned while venturing along The Upper Housatonic Valley African American Heritage Trail. The route tells the story of the region's most influential Black Americans — and spans from one end of the Berkshire County to the other and travels into Connecticut.

Along the trail, families can visit the site of W.E.B. Du Bois boyhood home. A founding member of the NAACP, Du Bois was a champion for the education of Black Americans, and "a central figure in twentieth-century movements for world peace, civil rights, and self-determination for people of African descent." ~ More about W.E.B. Du Bois can be found HERE

Also in Great Barrington is the site of the courthouse where Elizabeth "Mum Bett" Freeman, an enslaved woman working for the Ashley family, sued for her freedom and won. They can also visit the house in Sheffield where Col. John Ashley and Elizabeth Freeman lived. Before leaving Great Barrington, families might want to visit the boyhood home of W.E.B. Dubois, the founder of the modern Civil Rights Movement.

Next in Stockbridge, pay your respects to Elizabeth Freeman at the Stockbridge Cemetery, where she rests for eternity in the Sedgwick Pie. One might also like to stop by the Stockbridge Library to view the oil painting of Agrippa Hull, who along with his wife Margaret (Peggy) Timbroke, became some of the first black entrepreneurs in the Berkshires. 

Heading north, one can stop in Lenox where the first great African American photographer, James VanDerZee was born and raised, or visit the site of the former Music Inn which was a major venue for Black musical talent during the jazz age.

Discovering Black history sites in Pittsfield could take an entire day with over 10 sites commemorating the impact black individuals and families have made in the city in years past — Samuel Harrison, Alfred K. Persip, and Dorothy Amos, to name a few.

There are also several locations on the trail that are believed to have been stationed along the Underground Railroad such as Jacob's Pillow in Becket, Wizard Glen and the Historic Fitch-Hoose House in Dalton, as well as the Todd House (marked by a placard) in Lanesborough.

A final stop in Williamstown will bring you the childhood home of Pittsfield-born Hall of Fame Baseball player Frank Grant, which is just one of many individuals steeped in the Berkshires baseball history, (but that's a story for another time).

For more information about the trail visit

Download a map of the trail HERE and more Guides celebrating Black History in the Berkshires.