Downtown Winston-Salem is gearing up for its second annual Holiday Market and Tree Lighting on Saturday, Nov. 21, running from noon to 7 p.m. at 500 W. Fifth Street. The free event will feature more than 40 local artisan vendors, food trucks, live music, children’s activities, and the lighting of a 30-foot Christmas tree at 6 p.m.
The gathering is presented by 500 W. Fifth, and admission is free and open to the public, according to journalnow.com. Peyton Justice, 500 W. Fifth’s marketing and events manager, said the market aims to welcome neighbors, support local small businesses, and elevate the arts, as reported by Mark Burger in YES! Weekly. The event was designed to celebrate the spirit of the community, according to the same report.
Musician Martha Bassett, who hosts the Martha Bassett Show, will headline live music beginning at 3 p.m., with special guests joining her, per visitwinstonsalem.com's events guide. Kaleideum will run a kids’ station, and the event also includes a children’s holiday choir, according to the YES! Weekly report. Justice said the market offers smaller pockets of engagement, including s’mores, children’s activities, vendors and music.
Food, Drinks and a Beer Tent
Food trucks and drinks will be on hand throughout the afternoon and evening, and the visitwinstonsalem.com guide also notes free fireside s’mores and a Downtown Grille pop-up. Foothills Brewing will provide a beer tent at the market, per the YES! Weekly account. Justice said the event aims to foster togetherness and be accessible to all, the outlet reported.
A Bigger Turnout Expected
The holiday market began in 2025, when it attracted more than 2,000 attendees in its first year, Justice said, according to the YES! Weekly report. Organizers hope to double attendance at the 2026 market, per the same account. Last year’s inaugural event, held Nov. 22 from 2 to 7 p.m., featured a 35-foot Norwegian spruce from Sugar Mountain Nursery, with a crew using a lift to string about 20,000 lights on the tree, journalnow.com's event collection noted.
Street Closures and Weather Plans
Surrounding streets will close beginning at 11 a.m. on Nov. 21, according to the YES! Weekly report, while the 500w5th.com event page states that roads surrounding the building will be closed for safety from 11 a.m. to 8 p.m. that day. Organizers say the market will be canceled in the event of torrential weather, per journalnow.com, though the 500w5th.com page describes the cancellation threshold as inclement weather. Updates will be posted through the official 500 W. Fifth website and its Instagram and Facebook pages, according to the YES! Weekly account.
