Winston Salem Holiday Events

A Christmas Carol Cocktail Experience - Winston Salem

Roar 12 Dec 2025

Winston-Salem Ugly Sweater Bar Crawl

Winston-Salem 13 Dec 2025

Vienna Light Orchestra Christmas Tour 2025

R. J. Reynolds Memorial Auditorium 23 Dec 2025

2025 Vendor Christmas Market — The Faith Based Mom

Salem Christian School 13 Dec 2025

Vienna Light Orchestra Christmas Tour 2025

RJ Reynolds Auditorium 23 Dec 2025

Winston-Salem St. Patrick's Day Bar Crawl

Wise Man Brewing 14 Mar 2026

Heilige Nacht: Sacred Stillness (December 20)

St. Timothy's Episcopal Church, Winston-Salem, NC 20 Dec 2025

Christmas Drag Brunch

The Dutch Light 14 Dec 2025

Heilige Nacht: Sacred Stillness (December 19)

St. Timothy's Episcopal Church, Winston-Salem, NC 19 Dec 2025

I Am My Mother's Daughter Christmas Soiree

Cupcake Cuties Cafe & Bakery 13 Dec 2025

Lilly’s Network Holiday Party

S&G Event Center 13 Dec 2025

WOW Holiday Gathering

DISCIPLES OF GRACE MINISTRIES 19 Dec 2025

Jazz At Manolo's w/ The Matt Kendrick Trio

Manolo's Boutique Wines & Bistro 19 Dec 2025

The Grinch at Bookmarks

Bookmarks 20 Dec 2025

Season’s Best Carolers: Music, Joy, and Family Moments 🎄

151 S Stratford Rd, Winston-Salem, NC, United States, North Carolina 27104 20 Dec 2025

Janome Holiday Open House!

2705 Peters Creek Pkwy, Winston-Salem, NC 27127-4728, United States 13 Dec 2025

High School Reunion's Christmas Vacation

The Ramkat 12 Dec 2025

Healthy Holiday Experience

1460 Irving St., Winston-Salem, NC 13 Dec 2025

Salem Band Holiday Concert

Calvary Moravian Church 16 Dec 2025

Christmas for the City 2025

Benton Convention Center 20 Dec 2025

The First Annual FNMC Holiday Ball!

Wise Man Brewing 13 Dec 2025

An Enchanted Christmas at Reynolda

2250 Reynolda Rd, Winston-Salem, NC, United States, North Carolina 27106 13 Dec 2025

HO-B RC Christmas Crawl

Hanes Mall 13 Dec 2025

Morgan Wade: Home for the Holidays

The Ramkat 18 Dec 2025

Kaleideum After Dark: Twin City Santa

120 W 3rd Street, Winston-Salem, NC, United States, North Carolina 27101 13 Dec 2025

Holiday Pop-Up

Campus Gas 13 Dec 2025

2nd Annual Sneaker Ball

Elks Lodge #449 - Winston-Salem NC 13 Dec 2025

Candle-Making & Cheer at Foothills Brewing ️Tasting Room

Foothills Brewing Tasting Room 17 Dec 2025

W-S POPS Holiday Show JINGLE, JOLLY, JAZZ & HOLLY

Ardmore Baptist Church 18 Dec 2025

Holiday Candle Making Workshop

Lizzie’s All natural Products 12 Dec 2025

Holiday Dinner & Drinks

Earl’s WS 20 Dec 2025

Vintage Show at Wise Man

Wise Man Brewing 13 Dec 2025

Winston-Salem Cinco De Mayo Bar Crawl

Wise Man Brewing & Coffee Bar 5 May 2026

Creative Kids: Mini Gingerbread House Workshop

B Balanced Counseling & Wellness, PLLC 13 Dec 2025

2026 ANCHOR Christmas Party

Millennium Event Center 19 Dec 2025

Holiday Soap Making Workshop

Lizzie’s All natural Products 13 Dec 2025

Taizé Worship on the Longest Night

1000 Yorkshire Road, Winston-Salem, NC, United States, North Carolina 27106 18 Dec 2025

Santa Claus is Coming to Wise Man!

Wise Man Brewing 21 Dec 2025

DIY Holiday Floral Design Class – Benefiting The Haley Graves Foundation

Anne Marie Bridal Designs 12 Dec 2025

🌟 LET’S HAVE CHURCH! 🌟

2400 Dellabrook Rd, Winston-Salem, NC, United States, North Carolina 27105 21 Dec 2025

Santa Photo Party

2623 Wood Valley Rd 16 Dec 2025

Wise Man Brewing Christmas Party

Wise Man Brewing 13 Dec 2025

Santa Welcomes You & Your Wishes at Mast Store Winston-Salem

516 North Trade Street, Winston-Salem, NC 27101 13 Dec 2025

SANTA'S WORKSHOP: HOLIDAY FOOD CRAFTS

Southern Home & Kitchen 13 Dec 2025

Santa Claus is Coming to Wise Man!

Wise Man Brewing 20 Dec 2025

Southbound Craft Fair

Wake Forest Biotech Place 20 Dec 2025

Caroling Fridays at Reynolda

2250 Reynolda Rd, Winston-Salem, NC, United States, North Carolina 27106 12 Dec 2025

Holiday Legging Giveaway

110 Oakwood Drive, Ste D, Winston-Salem, NC, United States, North Carolina 27103 12 Dec 2025

A Holiday Martini Party with The Porch & Sutler's

840 Mill Works St, Winston-Salem, NC, United States, North Carolina 27101 18 Dec 2025

A Very Winston Painting Pop-Up at Wise Man

Wise Man Brewing 14 Dec 2025

Six Shooters and Q-Tone

Manolo's Boutique Wines & Bistro 18 Dec 2025

Arts at Ardmore Concert- Holiday Strings

Ardmore Baptist Church 21 Dec 2025

AAWS Artist Meetup - Holiday Celebration

Broad Branch Distillery 14 Dec 2025

The Fallen outdoors Holiday Market

Lexington NC 13 Dec 2025

Candle-Making & Cheer Creative Workshop at Wise Man Brewing & Coffee Bar

Wise Man Brewing & Coffee Bar 28 Dec 2025

2025 BRENNER JEEP TOY RUN FOR THE CHILDREN

2008 Queen St, Winston-Salem, NC 27103-2628, United States 21 Dec 2025

Mistletoe & Murder: A Holiday Murder Mystery Show - Radar Brewing Company

Radar Brewing Company 15 Dec 2025

Book Club & Jólabókaflóð Celebration

120 A Reynolda Village, Winston-Salem, NC, United States, North Carolina 27106 16 Dec 2025

Light a Luminary for Ronald McDonald House Charities Piedmont Triad

419 S Hawthorne Rd, Winston-Salem, NC 27103 24 Dec 2025

Robbie Fulks

626 South Main Street, Winston-Salem, NC, United States, North Carolina 27101 8 Mar 2026

Forsyth Hospital Presents a Holiday Market

Forsyth Medical Center 17 Dec 2025

Holiday Jazz with Martha Bassett and the Matt Kendrick Quartet

Intergenerational Center for Arts & Wellness 23 Dec 2025

St Philips Moravian Christmas Eve Lovefeast

911 S. Church Street, Winston-Salem, NC, United States, North Carolina 27101 24 Dec 2025

Camel City Jazz Orchestra 2025 Holiday Concert

UNC School of the Arts Gerald Freedman Theatre 17 Dec 2025

Pet Photos with Santa

3320 Silas Creek PKWY, Winston-Salem, NC 27103 15 Dec 2025

WAFER THIN performing live Dec. 19th @, MILLER'S on TRADE, Winston-Salem NC / FREE SHOW!!

Miller's on Trade, Winston-Salem NC 19 Dec 2025

Anne & the Moonlighters Holiday Special at Wise Man

Wise Man Brewing 12 Dec 2025

Cookies & Cocoa

202-B S. Stratford Rd, Winston-Salem, NC, United States, North Carolina 27103 22 Dec 2025

Ugly Sweater Party & Chicken Stew with Holiday Vendors at Bar Nola

1151 Canal Dr. Suite 105, Downtown Winston-Salem, NC 14 Dec 2025

Dirty Santa Bingo at Bar Nola

1151 Canal Dr. Suite 105, Downtown Winston-Salem, NC 16 Dec 2025

FNMC (Friday Night Music Club) Holiday Special w/ Doug Davis Fundraiser for Second Harvest Food Bank

Wise Man Brewing 13 Dec 2025

Dirty Santa Bingo at Bar Nola

1151 Canal Dr. Suite 105, Downtown Winston-Salem, NC 23 Dec 2025

The Yacht House Party Yuletide Jubilee

Joymongers Barrel Hall 21 Dec 2025

Christmas/Holiday Paint & Sip at The Dutch Light Cocktail Bar (21+)

The Dutch Light 26 Oct 2025