Current Events

Vancestock IX

Saturday, September 12, 2020 - 1:00pm

This year's event will be held on-site at Trails Lakeside, 15599 Warden Avenue.

Doors open at 1 PM and the show will start at 2 PM.

BYOC&B - Bring your own chair and beverage.

Musical lineup includes:
Bywater Call
Brothers & Sisters

Sunil Thomas Charity Golf 2020

Tuesday, September 15, 2020
We are excited to bring back our 3rd annual Sunil Thomas Charity Golf for Trails in September 2020. In honour of Sunil, his friends and family created a tournament to support youth as the perfect homage to this memory.

Inside Ride 2020

Postponed until further notice

Past Events

Scotiabank Toronto Waterfront Marathon - Run with Trails

Sunday, October 20, 2019

We hope you will partner with us through this year’s STWM and make a difference for our kids on October 20! No matter what distance you participate in, your fundraising changes lives.

Vancestock VIII

Thursday, October 10, 2019 - 6:00pm

Another epic Vancestock! If you couldn't make it, or you still feel like you're dancing in the dark, donations to Trails will be accepted until December 31st. Please click the "Accepting Donations" link.

Trails Lakeside Wellness Retreat

Saturday, September 28, 2019 - 9:00am to Sunday, September 29, 2019 - 4:00pm
Join us at Trails Lakeside for the first adult Wellness Retreat with yoga and art. Enjoy a beautiful and peaceful weekend getaway less than an hour outside of Toronto. Rest, rejuvenate and enjoy outdoor activities and incredible plant-based food while learning about wellness, mindfulness and health at informative workshops.

Sunil Thomas Charity Golf

Wednesday, August 7, 2019 - 7:00am to 3:00pm

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.

Frank O'Dea Speaker's Corner Series

Tuesday, June 18, 2019 - 6:00pm to 8:00pm

As a young man, Frank O'Dea was homeless, living on the streets, panhandling for nickels and dimes. Today, he is a celebrated business person. Best known as a founder of The Second Cup, he also was involved in founding a number of other successful international businesses and not-for-profits. Frank Inspires people to achieve inspiring results.

Graduation 2018

Saturday, June 1, 2019

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.

Inside Ride 2019

Wednesday, May 1, 2019 - 2:00pm to 4:00pm

The Trails Inside Ride is an organized stationary cycling challenge and celebration using state of the art stationary bikes equipped with odometers. Each cyclist rides at a comfortable pace for five minutes to fun, fast-paced music cheered on by his/her teammates.

Vancestock VII

Thursday, October 11, 2018 - 6:00pm

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).

Sunil Thomas Charity Golf

Thursday, September 13, 2018 - 7:00am to 3:00pm

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

Saturday, September 1, 2018 to Sunday, October 7, 2018

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

Saturday, July 7, 2018

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

Saturday, June 9, 2018 - 9:00am to 4:00pm

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

Tuesday, June 5, 2018 - 5:30pm to 7:30pm

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.

Inside Ride 2018

Tuesday, May 1, 2018 - 2:00pm

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

Thursday, October 12, 2017 - 6:00pm to 11:00pm

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

Saturday, June 3, 2017 - 11:00am

Celebrate our Year 4's and LITS success!

Alumni Reunion - 25th Anniversary

Thursday, May 11, 2017 - 7:00pm

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

Friday, April 28, 2017

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

Thursday, October 20, 2016 - 7:00pm to 11:00pm

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.