When you attend an event or purchase tickets in a raffle draw, you help provide mentoring programs to children and youth in our community.
We are excited to bring back our signature events this year: Wing & Pizza Night, in its 32nd year and Winding Roads, in its 11th year.
Click the links below for more details!
Check out the Community Events page for the events in support of us. Community Events Page
2026 Events
Wing and Pizza Night
May 2nd, 2026; Scugog Recreation Centre, Pad 1 (1655 Reach Street, Port Perry)
The 32nd annual Wing & Pizza Night returns on May 2nd! We are excited to welcome you back for a fun night of delicious wings and pizza, and some incredible prizes!
We are grateful to our sponsors and restaurant partners for their participation, we truly appreciate your support! Please click on link to see the full list of sponsors and restaurants.
Winding Roads
Saturday September 19th, 2026
In 2026, we are proud to focus on local talent. We are excited to welcome the Steve Waters Band as our headliner for this year’s festival, with supporting acts Red Cup County, Brodie Bell and Julia Middleton.
Your ticket includes a delicious BBQ dinner from Marwan’s Global Bistro, fan-favourite grilled BBQ corn, yard games, a photo booth, a silent/live auction, a raffle, and so much more!
Want the latest news on the 2026 concert?
Annual Holiday Market!
Saturday November 28th, 2026
Join us again for another year of the Port Perry Holiday Market! Shop incredible & talented local vendors and stock up for fantastic, homemade, and local Christmas gift ideas.
The annual market features local vendors showcasing their talents with a wide variety of items and gifts ready for the Holidays.
Would you like to sponsor one of our events? Reach out to Jackie to chat about the options!
Meghan Wetheral | Communications & Events Coordinator
Meghan.Wetheral@bigbrothersbigsisters.ca | 905-985-3733 ext. 4