NAACP Berkshire County Brings Juneteenth Celebration to Pittsfield June 21

The NAACP Berkshire County Branch is marking Juneteenth this year with one of its most ambitious celebrations yet—a free, all-day event on Sunday, June 21 that moves through the streets of Pittsfield from City Hall to Durant Park, weaving together Black American history, music, scholarship, and community in a program that looks to unite generations.

The day begins at 11:00 AM at Pittsfield City Hall with the raising of the Juneteenth Flag and a reading of the Emancipation Proclamation. At 11:30, a Freedom Walk procession carries participants down to Durant Park on Pittsfield's historic Black West Side, where the festival runs through 6:00 PM.

A Multigenerational Douglass Reading

At noon, the park stage becomes a forum for a community reading of Frederick Douglass's 1852 address, "What to the Slave Is the Fourth of July?"—organized with support from a Mass Humanities Reading Frederick Douglass Together grant, secured by Berkshire Community College in partnership with the NAACP. Now in its 17th year, the Mass Humanities program funds public readings of the speech across Massachusetts, believing, as the organization insists, that Douglass's words belong in public spaces.

The list of readers reflects the breadth of Berkshire civic and academic life: Dr. Frances Jones Sneed, Professor Emeritus of History at Massachusetts College of Liberal Arts; Dr. Will Singleton, former NAACP Berkshire County Branch president; Pittsfield Superintendent of Schools Latifah Phillips; Pittsfield City Councilor Alisa Costa; A.J. Enchill, founder and president of the Berkshire Black Economic Council; and students from Miss Hall's School and Berkshire Community College, among others.

Music, Dance, and Local Legends

The afternoon lineup on the Durant Park stage showcases the depth of homegrown black talent in the Berkshires. Soul-rock-jazz outfit Sample the Cat opens at 1pm, followed at 2pm by SashaK Beauty Bar's "Crowning Our Culture: A Juneteenth Cultural Hair Show," a celebration of Black hair history through live presentations and storytelling.

Then at 3:30pm, the stage belongs to Wanda Houston—the singer known as the “diva of the Berkshires”—for a set of jazz and R&B. Houston, who grew up singing in gospel choirs on Chicago's West Side and went on to perform with artists including Barbra Streisand, Patti Austin, Joe Cocker, and Celine Dion, settled in the Berkshires full-time in 2006 and has been a fixture of the region's music scene ever since. Soul line dancing with Shonda Evette and Erica Shrader follows at 4pm, with DJ YoungChamp (David Dias) keeping the energy going throughout the day.

Basketball, Kids, and Community

Running parallel to the festival stage is a 5-on-5 Basketball Tournament organized in partnership with Beat the Streets, the free youth basketball program founded by Dashine Moore. What Moore started in 2021 with about 30 kids has grown into a league serving more than 370 boys and girls across Berkshire County. 

Families will also find arts and crafts, a bouncy house, face painting, Storytime for Kids, and free books. Free ice cream from Cravins Ice Cream—sponsored by the Berkshire Regional Planning Commission—goes to the first 200 children, and all fathers in attendance receive a free lunch courtesy of the NAACP branch.

The celebration wraps at 5pm with the 2026 Student Scholarship Presentation, honoring Berkshire County students through the NAACP's ROPE (Rights of Passage and Empowerment) program.

"Juneteenth is not just a holiday," said Dr. Dennis Powell, president of the NAACP Berkshire County Branch. "It is a living tradition of memory, resistance, and joy."

The event is free and open to all. Durant Park is flat-level and wheelchair accessible. For more information, visit naacpberkshires.org.