Holiday events in Winston Salem

Winston-Salem Halloween Bar Crawl

Sat, 24 Oct at 04:00 pm Southern Drift Brewing Company

USD 10 TO 46 FITNESS

Cricket's Nest Fall Festival

Sat, 26 Sep at 09:00 am South Fork Community Center

ART

Cozy Sip & Create: Candle-Making Workshop at Foothills Tasting Room

Fri, 16 Oct at 06:00 pm Foothills Brewing Tasting Room

USD 46 TO 63 FITNESS

2026 WS Ambassadors Holiday Parade (OFFICIAL!)

Sat, 05 Dec at 05:00 pm 4th St at Poplar St, Downtown Winston-Salem, NC

HOLIDAY

Angelo Artisan's Holiday Market

Sun, 08 Nov at 12:00 pm Wise Man Brewing

HOLIDAY

Holiday Decor Swap

Sun, 27 Sep at 02:00 pm greeNest

FREE FITNESS

The Nutcracker by United European Ballet in Winston-Salem, NC

Wed, 16 Dec at 07:00 pm RJ Reynolds Auditorium

ART

Winston-Salem SantaCon Bar Crawl 2026

Sat, 12 Dec at 04:00 pm Wise Man Brewing & Coffee Bar

USD 0 TO 31 FITNESS

Santa Sessions 2026 Winston-Salem, NC

Fri, 13 Nov at 09:00 am 102 W 3rd St, Winston-Salem, NC 27101, United States

HOLIDAY

Pinochle Card Game

Thu, 13 Aug Brown & Douglas Neighborhood Center

FREE HOLIDAY

Christmas with Martha Bassett

Tue, 15 Dec at 07:30 pm Brendle Recital Hall

MUSIC

Christmas Wrapped in Brass

Sat, 05 Dec at 07:30 pm Brendle Recital Hall

MUSIC

The Great American Trailer Park Christmas Musical

Fri, 13 Nov at 07:30 pm Jamie Lawson Auditorium at the Ihrie Theatre

ENTERTAINMENT