Cycling Week in Winston-Salem May 27-29

Winston-Salem is gearing up for another thrilling Winston-Salem Cycling Classic (WSCC) event May 27-29, 2017. The three-day annual cycling event consists of UCI 1.1 (ME & WE) road races, USA Cycling PRT/USA Crit Series Criterium races (ME & WE) and a full schedule of USA Cycling sanctioned amateur racing.

The excitement from the races continues each night with Gears & Guitars, a downtown music festival featuring national acts kicking off Friday, May 26. This year's lineup features Corey Smith, Barenaked Ladies, MIPSO and Collective Soul among others.  

Use as your resource for a daily calendar of events, leisure hotel package options and tips for what to do and where to dine while in Winston-Salem.

To learn more about the annual Winston-Salem Cycling Classic, click here

Interested in learning more about Winston-Salem?  Click here to request our comprehensive visitors guide filled with detailed directories of hotels, attractions and a list of destination-defining festival and annual events to assist you.

Saturday, May 27 - Criterium Races & Kids Zone Program

The Criterium Races kick off Saturday, May 27 at Bailey Park in downtown Winston-Salem. The Men's and Women's races gear up at 9 a.m. and continue through approximately 6:30 p.m. See below for Saturday's full schedule: 

9 a.m. - Men’s Cat 4-5
9:45 a.m. - Men’s 55+
10 a.m. - 2 p.m. - Crumley Roberts Kids Zone Program
10:30 a.m. - Juniors
11:15 a.m. - Masters
Noon - Women’s Cat 1-5
1 p.m. - Masters 35+
2:15 p.m. - Men’s Cat 3
3:30 p.m. - Men’s Cat 1-2
5 p.m. - Women’s PRT/UCI
6:30 p.m. - Men’s PRT/UCI/USA Crit Series

Sunday, May 28 - Flow BMW Mountain Madness 

The Flow BMW Mountain Madness ride is a collaborative effort between the Winston-Salem Cycling Classic and the 3 Mountain Madness to bring a great charity bike ride to the Winston-Salem and triad areas.  Proceeds from the event go to two non-profits, the National Cycling Center located in downtown Winston-Salem, and the Armfield Civic and Recreation Center in Pilot Mountain, NC. The goal of the Flow BMW Mountain Madness cycling event is to provide a challenging and safe ride of this scenic area to showcase the beauty of the NC foothills region. 

This event features loop rides starting and finishing at the Armfield Center in Pilot Mountain, located 30 minutes north of downtown Winston-Salem. Rides begin at 8 a.m. and close at 2 p.m. (View the Routes Here)
Location: 873 W 52 Bypass, Pilot Mountain, NC, 27041.  

Interested in registering for the race? All registrants receive an event t-shirt, a finisher medal, post race food, entry to The Barenaked Ladies concert as part of the Gears and Guitars weekend celebration in Bailey Park in downtown Winston-Salem, entry for raffle prizes and a chance to win a weekend at Hotel Domestique with the use of a BMW convertible.
Introducing the “Robbie Ventura Challenge”: Be the top finisher to beat Robbie’s timed segment up Sauratown Mountain and win dinner with Robbie and Bob Roll!

Monday, May 29 - Road Race Day

Head out to Bailey Park downtown for the final race day of the Winston-Salem Cycling Classic. The WSCC is a UCI 1.1 and USA Cycling Pro0Road Tour sanctioned Road Race. Athletes from around the cycling world travel to Winston-Salem to collect UCI points and over $25,000 in prize money. The race circuit consists of a challenging route that travels over 8.5 miles around beautiful Winston-Salem.

Road Race Schedule:
10 a.m. - Women's UCI Road Race
1 - 4 p.m. - Winston-Salem Walk & Roll
2:15 p.m. - Men's UCI Road Race

See the official Road Race Routes below:


Gears & Guitars

One of spring's most highly anticipated events is back! Gears & Guitars music festival - a series of concerts at Bailey Park performed in conjunction with the Winston-Salem Cycling Classic kicks off Friday, May 26 in Bailey Park Downtown. Opening night features three country music performances: Eric Dodd, Muscadine Bloodline and Corey Smith.

The four-day concert series continues with national recording artist Collective Soul performing Saturday night and on Sunday, May 28, Gear & Guitars brings more hits with headliner Barenaked Ladies.

On Monday, May 29 G&G concludes with free Memorial Day performances featuring a number of local bands, food trucks and other family activities. The Memorial Day celebration at Bailey Park is from 1 to 7 p.m.
Find more information and purchase tickets at

Gears & Guitars is held rain or shine. There are no chairs or blankets permitted in the Pit Area directly in front of the stage. Food and beverage is available on-site during the concerts, please no outside food or beverage. No pets permitted other than service animals.


Book a Hotel Getaway During the Winston-Salem Cycling Classic

Click Here for the Winston-Salem Events Calendar


Where to Dine

With more than 100 locally-owned restaurants within the downtown, you and your guests will have plenty of dining options. Click here to check out our restaurant directory and sort by restaurant type and amenities offered.

To have a comprehensive Winston-Salem Wine & Dine Guide delivered to you, click here.  The guide is filled with a directory of restaurants, nightlife spots and Yadkin Valley wineries, making it the perfect companion to our Visitor Guide.  Or stop by the Winston-Salem Visitor Center where our courteous and well-trained staff of visitor information specialists are also pleased to assist you.  Our toll-free number is:  866.728.4200 or e-mail us at:  Our Visitor Information Center, located at 200 Brookstown Avenue, is open Monday through Friday, 8:30 a.m. - 5 p.m. and Saturdays, 10 a.m. - 4 p.m.