Upcoming Events

Vancestock VII

Mark your calendars, Vancestock fans!!  Vancestock VII will be held on Thursday, October 11, 2018 (after Thanksgiving). The event returns to the Adelaide Hall in Toronto and features Elton Rohn (the premier Elton John tribute act), Matt Weidinger and Sisters & Brothers (Logan &  Jessica & Siblings).


EchoAge is an online Birthday Party Service where kids get the gift they want AND give to Trails Youth Initiatives.

Past Events

Sunil Thomas Charity Golf

Join us as we celebrate Sunil Thomas's life with his favourite sport at the Angus Glen Golf Club and help the kids at Trails.

Trail Raisers CAN

We're so excited to introduce you to Chris & Natalie who are planning to hike the entire 900km of the Bruce Trail this September and are raising funds for Trails while they go!

Limberlost Challenge

Take part in a marathon at the Limberlost Forest and Wildlife Reserve. The 14, 28, or 56Km race follows historic lakeside, wetland, and boardwalk trails on a private reserve.

Alumni Activity Day

You asked for it and we are excited to be making it happen! Who's ready for a trip down memory lane? All Trails graduates are invited to us on Saturday, June 9th for a day of fun, nostalgia and reuniting as a Trails community.

Rick "Ozzy" Osborne Speaker's Corner Series

Hear from Rick "Ozzy" Osborne, a former bike gang enforcer, as he shares his life's journey. Rick's story highlights the importance of the Trails programme in our community and we hope you will be inspired to invest in the future of our kids. Tickets are complimentary, but must be reserved in advance.

Graduation 2018

Graduation is always a special time at Trails, where we celebrate the accomplishments of the Year 4 participants and Leaders-in-Training over their four and five years at Trails. We'd love to have you join us on Saturday, June 2 at the Trails Youth Initiatives Lakeside Facility for a BBQ lunch and celebration.

Inside Ride

Cycle for Trails!  Register today for the Inside Ride!  Be a Team Captain, or join a team!  Teams consist of up to six people riding for five minutes per person on state-of-the-art stationary bikes to raise money for Trails kids and have a lot of fun!

Vancestock VI

Vancestock VI held on Thursday October 12th, 2017 raised $43,000!  A huge THANK YOU to Vance Cooper for your tireless energy and efforts to help to the kids at Trails.  Our gratitude is endless.  Vancestock VII; Save the date-Thursday October 11th, 2018!

Annual Graduation Celebration

Celebrate our Year 4's and LITS success!

Alumni Reunion - 25th Anniversary

All past and present Trails staff and graduates are invited to join us to reconnect and celebrate the 25th Anniversary of Trails. Whether you are part of the first group at Trails or you graduated in the last few years, we hope to see you there!

Chords & Strings for Roots & Wings-Trails 25th Anniversary Concert

Join us for an evening of fabulous music with "Bay Street's Hardest Working Band", Men In Suits. Celebrate our 25th Anniversary with us and support the youth at Trails.

Roots & Wings Gala

Trails Youth Initiatives is pleased to present the 15th Annual Roots & Wings Gala. Join us and approximately 250 guests at Airship 37 in Toronto's Distillery District as we host an evening of dinner, drinks and entertainment to benefit Toronto's vulnerable youth.