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Saturday August 5th

Criterium Racing, Festival and Live Music at Bailey Park

The Winston-Salem Cycling Classic course has become known for its challenging route that loops up and around Bailey Park, offering some of the most exciting bike racing in the country.

Watch pros and amateurs compete all day and take in the extra entertainment at the festival in Bailey Park all afternoon.

We’ll have plenty of food trucks and a beer garden too, so plan to spend the day.

Then, stick around for our FREE (yes, FREE) concert into the night!

Criterium Racing

Our legendary WS Cycling Classic course returns this year, starting and ending again on the Vine Street hill, providing great views of dynamic racing and opening up all of Bailey Park for our festival.

Race Routes:

Course 1:

Course 2:

Category Distance Start Time End TimeTotal PayoutEntry Fee (1)
Juniors (10-14)30 Minutes8:00 AM8:30 AMMedals / 3$15
Junior (15-16 Cat 4/ Novice)30 Minutes8:00 AM8:30 AMMedals / 3$15
Men Cat 4/ Novice 30 Minutes8:40 AM9:10 AM$250 / 3$25
Master’s 55+30 Minutes9:20 AM9:50 AM$300 / 3$35
Master’s 45+ 30 Minutes10:00 AM10:30 AM$300 / 3$35
Women Cat 4/ Novice30 Minutes10:40 AM11:10 AM$250 / 3$25
Course Closed (Reset)40 Minutes11:10 AM11:50 AM
Master’s 35+40 Minutes11:55 AM12:35 PM$300 / 3$35
Juniors (15-16 Cat 1-4)

Juniors (17-18)
40 Minutes12:50 PM1:30 PM$1,000 / 10
Women Cat 3/440 Minutes1:45 PM2:25 PM$300 / 3$35
Women Cat 1/240 Minutes1:45 PM2:25 PM$400 / 3$35
Men Cat 3/445 Minutes2:40 PM3:25 PM$300 / 3$35
Men Cat 2/345 Minutes3:40 PM4:25 PM$400 / 3$35
Pro Women Cat 1/260 Minutes5:00 PM6:00 PM$12,500 / 25 (2)$0
Pro Men Cat 1/275 Minutes6:30 PM7:45 PM$12,500 / 25 (3)$0
(1) Entry fees increase by $10 after 6PM on Friday, September 9
(2) Courtesy of Novant Health Women’s Health
(3) Courtesy of Riazzi Rhyne & Swaim Investment Group


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LIve band performs in front of large crowd at Bailey Park in Winston-Salem

Free Live Music

6:00 PM – 11:00 PM

With help from our friends at Lidl, this year’s concert is free and open to the public all night long! 

Announcements on this year’s music lineups will be made sometime in May.

Performances by:

Better Than EzraBetter Than Ezra
The return of an enduring force in rock music since the early 1990’s with major billboard hits like “Good”.

1990’s Indie rock band with hits including “If You Could Only See”.

Cowboy MouthCowboy Mouth
Dishes up a highly entertaining and unique style of Rock and Roll gumbo.

Have a business that's interested in space at the festival?