The Winston-Salem Cycling Classic, in conjunction with the Gears & Guitars music festival, returns to the downtown area for the fifth consecutive year this Memorial Day weekend, giving cycling and music fans plenty to take part in over the next four days.

The weekend’s festivities begin Friday at 6 pm with a three-act concert, including headliner Corey Smith, before cycling takes center stage Saturday morning and throughout the extended holiday weekend.

Read more.


When Richard Emmett walks the streets of downtown Winston-Salem, his mind looks past the present landscape and sees shades of the past. Before Trade Street was the Arts District, it was known as Old Town Street, and it drew rural famers into town to sell their crops, specifically tobacco, at the city’s many tobacco warehouses.

Between the corn and tobacco, musicians would take up a spot, particularly old-time string bands hoping to gather a crowd from the streets. Artists like Ernest Thompson and the North Carolina Cooper Boys made their start here and in other corners of North Carolina before finding the limelight.


Bailey Park Hours7 am to Dusk


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