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Saturday August 5th

Fondos, Criterium Racing and Live Music at Bailey Park

It’s a full day of cycling fun!  Our Fondos will depart from Bailey Park in the morning.  Pick from two road distances and two greenway / gravel distances.  The racing will heat up all afternoon with the famed WS Cycling Classic men’s and women’s races capping off the action.  We’ll have food trucks and a beer garden (for adults 21+) all afternoon.  Make sure to stick around for the FREE concert into the night!

The Fondos
presented by Flow Automotive

This year has tons of options for the whole family!  Two road distances (68 and 42 miles) and two greenway/gravel distances (15 and 7 miles). And everybody meets back at Bailey Park for lunch and a cold beverage afterwards.  

Road Fondo Details

445 Patterson Avenue, Winston-Salem


Onsite Registration Opens:  6:30 AM
68 Mile Fondo Departure:  7:30 AM
42 Mile Fondo Departure:  8:00 AM
Food trucks available: 11:00 AM - 3:00 PM


Join us for a kickoff at our race headquarters downtown at Bailey Park.  Two road distance options will take you out of town and into our beautiful scenic backroads around Lake Tomalex, and get you back in time for a complimentary beer (21+) and lunch from one of a variety of food trucks on site.

Road Route Links:
68 Mile Fondo (2 rest stops)

42 Mile Fondo (1 rest stop)


Includes a free Gears & Guitars 2023 t-shirt (while supplies last), one drink coupon (beer for 21+), and a lunch voucher for redemption at any food truck.

until May 15th (cutoff date for jersey pre-orders)

$60 May 16th – July 1st

$65 after July 1st

Greenway / Gravel Fondo Details

Location: 445 Patterson Avenue, Downtown Winston-Salem
Onsite Registration Opens: 6:30 AM
Greenway/Gravel Departure: 10:00 AM
Food trucks available: 11:00 AM - 3:00 PM

Final schedule subject to change


The journey along the Long Branch Trail and Salem Creek Greenway allows participants to turn around at any point along the route or travel all the way out and around along the Salem Lake trail, one of Winston Salem’s most enjoyable rides. Two options for this ride include:

  1. Greenway: Long Branch Trail to Salem Creek Greenway to Salem Lake or water crossing and return (7 miles, 1 rest stop)
  2. Greenway/Gravel: Long Branch Trail to Salem Creek Greenway and around Salem Lake and return (15 miles, 1 rest stop)

Greenway / Gravel route link:


Includes a complimentary t-shirt (while supplies last), one beer coupon (21+), and a lunch voucher for redemption at any food truck.


$55 until May 15th (cutoff date for jersey pre-orders)

$60 May 16th – July 1st

$65 after July 1st


Criterium Racing

The Winston-Salem 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. This year we will start and end again on the Vine Street hill! Watch pros and amateurs compete all day and take in the extra entertainment at the festival in Bailey Park. 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!

This year’s total race winnings purse is nearly $30,000 thanks to the support of Riazzi, Rhyne and Swaim investment Group.

Amateur Criterium Racing: 9:10 AM – 5:00 PM
Professional Criterium Racing: 5:30 PM – 8:15 PM

Schedule subject to change.

Race Routes:

Course 1:

Course 2:

Criterium Race Details

Juniors (10-14) and Junior (15-16 Cat 4/Novice)30 Minutes9:10 AM9:40 AM$20 Medals
Men Category 4/Novice30 Minutes9:50 AM10:20 AM$40 $250/3 Places
Women Category 4/Novice30 Minutes10:30 AM11:00 AM$40 $250/3 Places
Masters 45+, 55+ (Cat 1-4)40 Minutes11:10 AM11:50 AM$40 $300/3 Places Each Age Group
Women Category 3,4 30 Minutes12:00 PM12:30 PM$40 $300/3 Places
Juniors (15-16 Category 1/2/3) and Juniors (17-18)40 Minutes12:40 PM1:20 PM$20 $1,000/10 Places (Combined)
Course Closed (Reset)60 Minutes1:30 PM2:30 PM
Masters 35+ (Category 1-4)40 Minutes2:40 PM3:20 PM$40 $300/3 Places
Men Category 3/440 Minutes3:30 PM4:10 PM$40 $300/3 Places
Men Category 2/340 Minutes4:20 PM5:00 PM$40 $400/3 Places
Pro Women Category 1/2 60 Minutes5:30 PM6:30 PM$0 $12,500/25 Places*
Pro Men Category 1/275 Minutes7:00 PM8:15 PM$0 $12,500/25 Places*

* Courtesy of Riazzi Rhyne and Swaim Investment Group

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

Free Live Music

6:00 PM – 11:00 PM

This year’s concert is again FREE and open to the public all night long!  Announcements on music lineups will be made sometime in May.  Stay tuned!

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?