Winding Roads Festival 2019 Lineup

Winding Roads Festival is an annual Music Festival held in support of Big Brothers Big Sisters of North Durham. It brings in top country acts from all over Canada, to our little home in Port Perry. This year the lineup will include George Canyon, Charlie Major, Marshall Dane and Robyn Ottolini. More acts will be announced at the end of April. We guarantee you the artist that will join this lineup will make this years festival the biggest yet!

In the past 3 years Winding Roads has had performances from artists such as: The Road Hammers, Brad James, Ben Hudson, Kris Barkley, Aaron Pritchett, James Barker Band and Madeline Merlo. We draw from the deep well of our local cultural assets to make this night complete with food included in your ticket price. We use local produce and meats prepared by the chefs, farmers and the artisans that make Port Perry the jewel of Durham Region.

The youth of BBBSND take part in the festivities. During setup, they have the chance to learn about concert production with the engineers that has designed systems for Drake, Imagine Dragons and Shawn Mendes. Performing artists open up a private sound check and meet and greet, so our youth have a chance to gain insight into the world of preforming arts. 

Winding Roads is held the grounds of global loudspeaker manufacturer, Adamson Systems Engineering. 38 acres of M2 industrial land has been granted a 3 year permit (spanning to 2020) to host the festival. Over the past three years it's hosted thousands of guests, enjoying some of todays top country artists. It has grown every year.

Buy your ticket now and be prepared for pleasant artist announcements in the coming months. "To see the growth in our festival, along with offering unique opportunities for our youth (littles) to be involved with the events was exactly what we set out to achieve in 2016. We want to become a part of the community, it's culture and ensure future of children that grow up in North Durham have every chance possible to grow and excel. " - Margaret Ayres (Executive Director of Big Brother Big Sisters of North Durham).


  • Leading Country artists from all over Canada in Port Perry Ontario including George Canyon, Charlie Major, Marshall Dane and Robyn Ottolini.
  • Locally sourced food prepared by the leading culinary minds of Durham Region 
  • More than $100,000 raised in 2018 with all proceeds benefiting Big Brothers Big Sisters of North Durham
  • Local Brewery Old Flame providing beverages
Join us this year as we continue to grow and offer more opportunities for our youth to learn about their potential amongst leaders in production and musical performance. 

Sponsorship Opportunities

Winding Roads is only possible because of the sponsors that support our events. Our sponsors are the reason that the youth of Big Brothers Big Sisters of North Durham have the best opportunities through our events and the programs we provide. Please contact us to learn more about the sponsorship packages we offer and support this great cause. 

Big Brothers Big Sisters of North Durham

905-985-3733 Ext 1

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