Winding Roads Live

05/29/2026

The first hint has officially dropped for this year's Winding Roads Music Festival lineup! Any guesses?

The lineup will be announced on Friday, June 5th. Stay tuned as tickets will be announced on June 1st! Stay tuned as we gear up to release more details!

04/17/2026

The moment you've all been waiting for.....

SEPTEMBER 19TH. Winding Roads 2026.

More details about tickets coming soon!

09/24/2025

09/23/2025

A huge thank you to everyone who joined us at Winding Roads on Saturday night, we had an absolute blast! 🎉

All prize raffle winners have been contacted and have claimed their prizes. We do have two outstanding tickets from the Putting Contest hosted by Right At Home Realty in Port Perry. The winning ticket numbers are: #50317519 and #50317511.

If you hold one of these tickets, please contact us at 905-985-3733 ext. 4 or email [email protected]
to claim your prize.

A special thank you to for hosting the putting contest, it was so much fun! ⛳

09/21/2025

What an unforgettable night! Celebrating the 10th anniversary of Winding Roads with all of you was everything we could have hoped for and more. The evening was filled with incredible music, delicious food, and the best company of friends and supporters, we will treasure these memories forever.

A heartfelt thank-you goes out to our amazing sponsors, and prize donors, whose continued generosity makes this event possible year after year. To our volunteers, who pour in so much time and energy, you are truly the heart of Winding Roads. And of course, to everyone who attended and helped create such a magical atmosphere, we are so grateful.

We still have some cleanup ahead of us, but it’s all worth it. Soon, we’ll be sharing plenty of photos, videos, and highlights so you can relive the night with us, stay tuned!

For now, we want to send a special shout-out to , .waters.band, , and .official for bringing the stage to life with such incredible performances. Your talent made the night extraordinary.

Most importantly, to our sponsors, volunteers, and attendees, thank you for helping us continue to support children and youth in North Durham through our mentoring programs. Winding Roads wouldn’t be possible without each and every one of you, and we are endlessly grateful.
.insurance.investments .photobooth

09/20/2025

🎉 The Day Has Arrived! 🎉

Are you ready to kick off an unforgettable night of music and fun? Because we sure are! Join us under the big tent as we celebrate with amazing tunes, great vibes, and a whole lot of energy. Grab your friends, bring your excitement, and let’s make some memories together! 🎤🎸
.waters.band

09/20/2025

Our signs are looking absolutely SENSATIONAL for Winding Roads! We can’t wait to welcome you tomorrow and show you the full event set-up, complete with all of the incredible signs created by Sensational Signs.

We are so grateful to Brenda and her amazing team, not only for their creativity and talent, but also for the many acts of random kindness they continuously extend to our charity and to the wider community. Their generosity and support truly help bring our vision to life, and we couldn’t do it without them. Thank you !

09/19/2025

🎶 The Final Countdown is On! 🎶

Winding Roads is just 1 day away!
Get ready to experience an unforgettable night of music on September 20th with incredible performances by , , .waters.band, and . This is set to be the largest concert event in North Durham, an evening you won’t want to miss!
Bring your friends, feel the music, and make memories that will last a lifetime. See you there! 🎸✨