Fall & Winter Races in Winston-Salem

Jacob Gauthier

August 26, 2026

It’s 5K season! Whether you’re a race enthusiast or a casual runner looking to support a cause, check out these fall & winter races in Winston-Salem.

Updated August 2026

Mistletoe Run | Photo courtesy of the Mistletoe Run

Miles for Migraine

WHEN | Saturday, September 12
WHERE | Jamison Park

5K and 2-mile walk
Dress in your best purple attire for the chance at a prize
Benefits Miles for Migraine’s free programs and the Comprehensive Headache Program at Atrium Health Wake Forest Baptist

Moonlight Madness

WHEN | Saturday, September 12
WHERE | Bailey Park

5K, Monster Mile, and 1-mile fun run
Runs take place at night
Benefits the United Way of Forsyth County

Dirty Dozen

WHEN | Saturday, September 12
WHERE | Jerry Long Family YMCA

5K and 1-mile fun run
Multiple heats, starting every 10 minutes
Includes an obstacle course with a mud pit, climbing wall, balance beam, and more
Benefits YMCA health programs, including those benefiting cancer survivors and individuals managing chronic diseases

Salem Lake Trail Run

WHEN | Saturday, September 26
WHERE | Salem Lake

30K, 7-mile run, and 5K
Benefits the Salem Lake Trail System, the Winston-Salem Street School, and the Down Syndrome Association of Greater Winston-Salem

Maddie’s Miles

WHEN | Saturday, October 3
WHERE | Jamison Park

5K
Run with adoptable dogs from Ruff Love Rescue
Benefits Phoenix Rising of Winston-Salem, Inc., a non-profit that combats addiction through local drug court support

Mission 5K

WHEN | Saturday, October 3
WHERE | Fleet Feet Clemmons

5K and 1-mile fun run
A portion of proceeds benefits Good Works Engine, a nonprofit that helps those in need in our local community and abroad

Running Scared

WHEN | Saturday, October 3
WHERE | Jamison Park

13K and 5K
Race in your Halloween costume

Divine Llama Haunted Wine Run

WHEN | Sunday, October 4
WHERE | Divine Llama Vineyards

5K
Benefits Nik’s Wish, a nonprofit that grants wishes to young adults (ages 18-24) battling cancer

All Mounds Matter

WHEN | Sunday, October 4
WHERE | Savage Roasters Coffee

5K and 1-mile fun run
Benefits Cancer Services

Ardmore RAH!

WHEN | Saturday, October 17
WHERE | Redeemer Presbyterian Church

10K, 5K, and 1-mile fun run
Fun Fact: RAH stands for Run Against Hunger
Benefits Second Harvest Food Bank of Northwest NC

NCANA Run for Joy

WHEN | Saturday, October 24
WHERE | Jamison Park

5K
Proceeds support programming to increase awareness of mental health issues and promote mental wellness and advocacy

Flat & Fast Rural Hall

WHEN | Saturday, October 24
WHERE | Rural Hall Elementary School

5K
Race in your Halloween costume
Benefits Rural Hall Elementary School

Harvest Hustle

WHEN | Saturday, November 14
WHERE | Ivey Redmon Sports Complex

5K, 1-mile fun run, and 300-meter kids dash
Includes a team prediction challenge where teams race to match their predicted finish time
Benefits The Kernersville Foundation

Miles for Meals

WHEN | Saturday, November 7
WHERE | Tanglewood Park

5K
Run through the Tanglewood Festival of Lights at night
Benefits Hillsdale Church Food Ministry

Turkey Strut

WHEN | Thursday, November 26
WHERE | Winston-Salem Fairgrounds

5K and fun run
Bring at least 3 canned food items to donate to the We Care House food bank
Benefits the We Care House of Winston-Salem

Black Friday Relays

WHEN | Friday, November 27
WHERE | Salem Lake

20K relay, 15K relay, 10K relay, and 5K
Drop off your used running shoes to be donated to Sneakers4Good
Benefits the Down Syndrome Association of Greater Winston-Salem and the Winston-Salem Street School

Mistletoe Run

WHEN | Saturday, December 5
WHERE | William G. White, Jr. Family YMCA

Half marathon, 5K, and 1-mile fun run
Celebrate your finish with donuts
Benefits the YMCA of Northwest NC

Jingle Jog

WHEN | Saturday, December 19
WHERE | Fiddlin’ Fish Brewing

5K and 0.8-mile fun run
Run with your own dog or an adoptable dog from Ruff Love Rescue
Benefits Ruff Love Rescue

Running of the Lights

WHEN | Friday, January 1, 2027
WHERE | Tanglewood Park

5K and 1.75-mile fun run
Races start at midnight; start the new year with a run through the Tanglewood Festival of Lights

Frosty Fifty

WHEN | Friday & Saturday, January 8 & 9, 2027
WHERE | Salem Lake

Saturday morning: 50K relay, 50K, 25K, and 12.5K | Friday night: 5K
Benefits the Down Syndrome Association of Greater Winston-Salem and the Winston-Salem Street School

Are you planning to sign up for one (or several) of these races? Meet fellow runners at one of these local running clubs!