Events

Gears & Guitars Music Festival

Gears & Guitars music festival will be lighting up Bailey Park this year in conjunction with the Winston-Salem Cycling Classic races featuring the best in world class cycling, national and local musical acts and lots of fun events for everyone. Admission for this year is free and will be in two locations so please check the website for times, locations and updates.

Bailey Park

Free

I Dream of You

Always Chasing Sunsets, LLC is owned by David Bower, and is focused on providing safe spaces for self expression for LGBTQIA2S+ people through dance music and art. I Dream of You is a ticketed community event that will include a lineup of all LGBTQIA2S+ artists spinning a variety of dance music styles under the umbrella of deep melodic house music, progressive house and trance.

Bailey Park

$7 – $30

2023 Juneteenth Festival

Join the Triad Cultural Arts Juneteenth Festival on Saturday, June 17, in the Innovation Quarter Biotech Place (575 Patterson Ave.) from 1 p.m. to 5 p.m. for performances, exhibits, crafts, music and more. The celebrations continue outside in Bailey Park (445 Patterson Ave.) from 1 p.m. to 8 p.m. with vendors, displays, music and food.  […]

Bailey Park

The Big Chill

The Big Chill is a free ice-cream-themed fundraising event hosted by The Shalom Project. The Big Chill will feature free samples of dozens of flavors of homemade ice cream, prepared by members of the community, as well as Cheerwine floats, food trucks, live music, face painting, and more! The Shalom Project is a nonprofit organization […]

Bailey Park

Free

Gears & Guitars 2023

Gears and Guitars is back in 2023 for it’s tenth year! One of the country’s most prestigious cycling events combined with live music for a weekend of exciting racing, local riding and a full weekend of FREE live music from big name bands.

Innovation Quarter

Varies

5th Annual LeanBack GiveBack Block Party

We're are looking forward to the 5th Annual LeanBack GiveBack Block Party it's going to be AMAZING! But here's the best part – it's all for a fantastic cause! We are giving back to the community that has given so much to us and we need YOU there to make it happen. Together, we can create something truly special.

Bailey Park

Free

Christmas in the Coalpit Vendor Market

Ready to get Christmassy? Don't miss Christmas in the Coalpit presented by Manda's Creations Mobile Shop, The Thrifty Gifter and Incendiary Brewing Company. Join us on Sunday, Dec. 3rd from 12-4 p.m. to shop from 30+ vendors, meet Santa, groove to live music, enjoy face painting and grab a pint.

Coal Pit at Bailey Power Plant

Varies

Chanukah Menorah Lighting

Join us for a fun Chanukah celebration in Bailey Park! Watch chocolate coins fall from the sky during our Gelt Drop from the top of a fire truck's ladder! Enjoy tasty hot latkes and donuts, get creative with Chanukah crafts, and have a blast with balloon twisting. And don't miss the lighting of the giant menorah! It's all free and open to everyone in Winston Salem. Bring the whole family and spread the word!

Bailey Park

Free

JF Realty Egg Hunt

Join us for the 4th Annual Easter Egg Hunt & Food Drive on Saturday, March 23rd from 10 a.m. to noon at Bailey Park in Winston-Salem.

The event will include an egg hunt, face painting, balloon artistry, and a magic show. Make sure to check in and receive your free mini donuts and hot drink from Lil' Donuts food truck. We will also be collecting food donations to benefit the Winston-Salem Rescue Mission.

Parking is available on Patterson Avenue between 4th and 5th Streets or at the Church Street Parking Deck. 

Huge thanks to our sponsors for the event include Atlas Orange, Highlands Mortgage, Clemmons Carpet, Josh Jarvis NC Farm Bureau, and Assurance Home Inspections. Don't miss out on this fun-filled event for all ages!

Bailey Park

Free

Fake Frown’s Talent Wins

Join us at Bailey Park in Downtown Winston-Salem for live performances, an open mic, local vendors, and food. The event is hosted by kamauislost with performances from Rollin$toneKC, WesttEndWay, RTB Ross, Progress Ink, and more!

Bailey Park

Free

Maya Angelou Garden Party

The Maya Angelou Garden Party is an annual event hosted in Bailey Park to honor Dr. Maya Angelou by celebrating community, storytelling, and art. Each year this event is free and open to both the public and broader community, with poetry reading and spoken word performances on display to honor Dr. Angelou’s literary legacy. Food, music, and lawn games are also part of the celebration.

Bailey Park

Free