The Latest Go-To Newsletter: 
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.
Register ahead of time to get an early bird discount on some of these races!
Updated January 2026
Miles for Migraines
WHEN | Saturday, September 6
WHERE | Jamison Park
- Free to register
- Races start at 9:30 AM
- Benefits the Comprehensive Headache Program at Atrium Health Wake Forest Baptist
Moonlight Madness 5K and Monster Mile
WHEN | Saturday, September 6
WHERE | Bailey Park
- Races start at 7:20 PM
- Benefits the United Way of Forsyth County
Dirty Dozen 5K and Fun Run
WHEN | Saturday, September 13
WHERE | Jerry Long Family YMCA
- Races start at 7:30 AM
- This event is an obstacle mud run—you can expect to encounter a mud pit, climbing wall, balance beam, and more!
- Benefits YMCA health programs, including those benefiting cancer survivors and individuals managing chronic diseases
Walk & Roll Fest
WHEN | Saturday, September 13
WHERE | Truist Stadium
- Races start at 8:30 AM
Salem Lake Trail Run
WHEN | Saturday, September 27
WHERE | Salem Lake
- Races start at 8 AM
- Benefits the Down Syndrome Association of Greater Winston-Salem and Winston-Salem Street School
Maddie’s Miles
WHEN | Saturday, October 4
WHERE | Jamison Park
- Race starts at 9 AM
- Participants can 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 4
WHERE | Fleet Feet Clemmons
- Race starts at 8 AM
- A portion of proceeds benefits Good Works Engine, a non-profit that helps those in need in our local community
Divine Llama Haunted Wine Run 5K
WHEN | Sunday, October 5
WHERE | Divine Llama Vineyards
- Race starts at 12 PM
- Benefits Nik’s Wish, a non-profit that grants wishes to young adults (ages 18-24) battling cancer
All Mounds Matter 5K
WHEN | Sunday, October 5
WHERE | Savage Roasters Coffee
- Races start at 9 AM
- Benefits Cancer Services
Ardmore RAH!
WHEN | Saturday, October 18
WHERE | Redeemer Presbyterian Church
- Races start at 8 AM
- Benefits Second Harvest Food Bank of Northwest NC
Running Scared 5K/13K
WHEN | Sunday, October 19
WHERE | Jamison Park
- Races start at 2 PM
- Benefits the Arts Council of Winston-Salem and Forsyth County
Race for the Fallen Glow Run
WHEN | Friday, October 24
WHERE | Bailey Park
- Races start at 6:45 PM
- Benefits the families of fallen law enforcement officers through the Police Benevolent Foundation
Flat & Fast Rural Hall 5K 10K
WHEN | Saturday, October 25
WHERE | Mayflower Seafood Restaurant
- Races start at 8 AM
- Halloween costumes encouraged for the 5K—there will be a costume contest with prizes
- Benefits Rural Hall Elementary School
Nailed It! 5K Pumpkin Run/1 Mile Fun Walk
WHEN | Saturday, October 25
WHERE | Harmon Park
- Races start at 3:30 PM
- Costumes encouraged—there will be a costume contest with prizes
- A portion of proceeds benefits The Kernersville Foundation
NCANA Run for Joy 5K
WHEN | Saturday, October 25
WHERE | Jamison Park
- Race starts at 9 AM
- Proceeds go to a scholarship for counseling for medical trainees in need of financial support at Wake Forest School of Medicine
Miles for Meals 5K
WHEN | Saturday, November 8
WHERE | Tanglewood Park
- Race starts at 5:30 PM
- Benefits Hillsdale Church Food Ministry
Salute to Service 5K
WHEN | Saturday, November 8
WHERE | Salem Strollway
- Race starts at 8 AM
- Benefits Veterans Helping Veterans Heal
Turkey Strut 5K
WHEN | Thursday, November 27
WHERE | Winston-Salem Fairgrounds
- Races start at 8:30 AM
- Benefits the We Care House of Winston-Salem
- Participants are asked to bring at least 3 canned food items to donate to the We Care House food bank
Black Friday Relays
WHEN | Friday, November 28
WHERE | Salem Lake
- Races start at 9 AM
- Benefits the Down Syndrome Association of Greater Winston-Salem and Winston-Salem Street School
YMCA Mistletoe Run
WHEN | Saturday, December 6
WHERE | William G. White, Jr. Family YMCA
- Races start at 7:30 AM
- Benefits the YMCA of Northwest North Carolina
Jingle Jog
WHEN | Saturday, December 20
WHERE | Fiddlin’ Fish Brewing
- Races start at 9 AM
- Participants can run with adoptable dogs from Ruff Love Rescue
- Benefits Ruff Love Rescue
Running of the Lights
WHEN | Thursday, January 1, 2026
WHERE | Tanglewood Park
- Races start at 12 AM
Frosty Fifty
WHEN | Friday & Saturday, January 2 & 3, 2026
WHERE | Salem Lake
- Race on Friday starts at 5:30 PM
- Races on Saturday start at 8 AM
- Benefits the Down Syndrome Association of Greater Winston-Salem and the Winston-Salem Street School
48 Miles of HOPE
WHEN | Saturday, February 7
WHERE | Kimberly Park
- Races start at 7 AM
- Benefits H.O.P.E. of Winston-Salem, a non-profit that helps curb food insecurity for families in Forsyth County
Are you planning to sign up for one (or several) of these races? Meet fellow runners at one of these local running clubs!
