Touring Through Winston-Salem’s African American Past, Present & Future

Just across the creek from Winston-Salem’s historic district of Old Salem sits a quiet hilltop community with a picturesque view of Winston-Salem. Christened “Happy Hill” more than a hundred years ago, the unassuming urban neighborhood might seem like any other. But hop on a Segway (or trolley) under the guidance of local historian Cheryl, and you’ll quickly unravel the secrets of its remarkable past.

Settled first as a so-called “urban plantation” to support the nearby farming community of Wachovia (now Winston-Salem), this former slave encampment was eventually reclaimed by newly freed African Americans. The influx of freed black residents turned Happy Hill into the first and now the oldest black neighborhood in the region. By 1867, Happy Hill became home to one of the first schools in the country specifically built for African Americans after the Civil War.

That’s a lot of history to glean from a single historical marker. Fortunately, thanks to the specialty guided tours from Triad Eco Adventures and Triad Cultural Arts, you don’t have to.

Guided Segway Tours of African American History

Spearheaded by Cheryl Harry, noted historian and national expert on black and African American history, these tours combine her knowledge of local history with the convenience of rolling Segways offered by Triad Eco Tours. The African American Heritage tour makes multiple stops throughout the city, including Happy Hill, historic Old Salem, downtown Winston-Salem and other sites of historical African American significance.

Here’s a taste from a recent tour. Starting from a central location just south of Old Salem Museums & Gardens, groups glide on Segways through multiple stops including St. Phillips African Moravian Church, the oldest standing African American church in North Carolina, Happy Hill neighborhood, notable buildings fashioned by nationally recognized master brick mason George Black, and more.

The tours are visitor-friendly and run approximately two hours.

To learn more about these guided tours, or to schedule yours now, contact Triad Eco Adventures at their website here.

Custom Group Tours of African-American History

For those interested in a deeper dive into Winston-Salem’s treasured African American past, Henry recommends custom-guided African American Cultural Trolley Tours. Designed to meet the needs of small groups, families (weddings, reunions), leadership organizations, students, and cultural visitors, these custom tours will take you off the beaten path into touchstones of the Black experience.

This tour features some of the city’s most treasured historic gems and cultural sites from various periods in the city’s Black history. Topics and sites featured include (varies per tour):

  • Delta Arts Center
  • Diggs Gallery at Winston-Salem State University
  • Sculpture Gardens at Winston-Salem State University
  • Historic homes and neighborhoods
  • St. Phillips African Moravian Church
  • Artistic Scavenger Hunt
  • North Carolina’s first urban Rosenwald School (schools and shops built for the purpose of African American education in the South during the early 20th century.)
  • Freedmen’s Graveyard

To learn more about scheduling a custom group tour, or to inquire about specific dates or times for any African American heritage tour, contact Cheryl Harry at or visit