Winston Salem Holiday Events

2026 WS Ambassadors Holiday Parade (OFFICIAL!)

4th St at Poplar St, Downtown Winston-Salem, NC 5 Dec 2026

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

Foothills Brewing Tasting Room 16 Oct 2026

Winston-Salem SantaCon Bar Crawl 2026

Southern Drift Brewing Company 12 Dec 2026

Santa Sessions 2026 Winston-Salem, NC

102 W 3rd St, Winston-Salem, NC 27101, United States 13 Nov 2026

Brunch with Santa at Another Broken Egg Cafe

Another Broken Egg Cafe 5 Dec 2026

4th Annual Holiday Bar Crawl

Downtown Winston-Salem 6 Dec 2026

Santa Photos

3320 Silas Creek PKWY, Winston-Salem, NC 27103 11 Nov 2026

Holiday Sunday Funday Candle Making Workshop at Fiddlin' Fish

Fiddlin' Fish Brewing Company 6 Dec 2026

Holiday Brunch: A Deliciously Festive Gathering

Southern Home & Kitchen 14 Nov 2026

Pet Photos with Santa

3320 Silas Creek PKWY, Winston-Salem, NC 27103 16 Nov 2026

The Great American Trailer Park Christmas Musical

Jamie Lawson Auditorium at the Ihrie Theatre 13 Nov 2026

Christmas Wrapped in Brass

Brendle Recital Hall 5 Dec 2026

Latin Night at Dave & Buster's

Dave & Buster's (Winston-Salem, NC) 20 Nov 2026

Caroling Fridays at Reynolda

2250 Reynolda Rd, Winston-Salem, NC, United States, North Carolina 27106 4 Dec 2026

Christmas with Martha Bassett

Brendle Recital Hall 15 Dec 2026

Cookies with Santa at The Ridge Event Venue

4810 Serenity Hills Lane, Winston-Salem, NC, United States, North Carolina 27127 20 Dec 2026

Gays and Theys-giving Holiday Potluck

930 Burke St, Winston-Salem, NC, United States, North Carolina 27101 21 Nov 2026

Kaleideum After Dark: Holiday Haute Mess

120 W 3rd Street, Winston-Salem, NC, United States, North Carolina 27101 12 Dec 2026

HYPE URBAN LINE DANCE BEGINNER BASH

WR Anderson Rec Center (Reynolds Park) 21 Nov 2026

Thankful Market at Wise Man Brewing

Wise Man Brewing 21 Nov 2026

Pinochle Card Game

Brown & Douglas Neighborhood Center 12 Nov 2026

Holiday Gift Skill Share- Make & Take Gifts

18 Springs 14 Nov 2026

Small Business Saturday at Oasis at The Mill

918 Bridge Street. NW, Winston-Salem, NC, United States, North Carolina 27101 28 Nov 2026

Small Biz Saturday Shopping Sales at CasaShanti

545 N Trade St. Unit 100, Winston-Salem, NC, United States, North Carolina 27101 28 Nov 2026

Sawtooth Spotlight: Holiday Market

251 N Spruce St, Winston-Salem, NC, United States, North Carolina 27101 5 Dec 2026

High School Reunion's Christmas Vacation

The Ramkat 4 Dec 2026

Winston-Salem Triad Clinical Connections - (December Holiday Edition)

Wise Man Brewing & Coffee Bar 4 Dec 2026

Now That's What I Call Dad Rock

The Den 20 Nov 2026

Shine A Light on Hunger

127 Cascade Ave, Winston-Salem, NC 27127-2026, United States 5 Dec 2026

The Calm Before the Rush: A Restorative Evening of Rest, Sound & Stillness, with Veda Spidle

612 N Trade St., Winston-Salem, NC, United States, North Carolina 27101 18 Nov 2026

"Make & Take It” Abundance & Gratitude Simmer Pot

545 N Trade St. Unit 100, Winston-Salem, NC, United States, North Carolina 27101 18 Nov 2026

ALA Unit 55 Fall/Holiday Vendor Fair, Breakfast and Brunch

American Legion Auxiliary Unit 55 NC 14 Nov 2026

Core Church Annual Holiday Breakfast

534 Oak Summit Rd 12 Dec 2026

Wonderfully Made Art Fair

Maple Springs United Methodist Church 1 Dec 2026

Dull Mourning, Selfish Means, Chained, Fliora, All Alone & Dying Day

Gas Hill Drinking Room 20 Dec 2026

Holiday Open House

1100 W. First Street 1 Dec 2026

Reynolda Village Holiday Stroll

2201 Reynolda Rd, Winston-Salem, NC, United States, North Carolina 27106 21 Nov 2026

Carolina Dogwood Mistletoe & Milestones

Winston-Salem Regional Association of REALTORS 17 Dec 2026

Holiday Appetizers: Small Bites, Big Holiday Flavor!

Southern Home & Kitchen 17 Nov 2026

Auditions - Intimate Apparel

LTWS Pirolo Joyce Center, 4015 Brownsboro Rd, Winston-Salem, NC 27106-3380, United States 16 Nov 2026

AARF Adoption Fair

302 Thurston Street, Winston-Salem, NC, United States, North Carolina 27103 24 Oct 2026