Scavenger Hunt

Register for the 2026 Big on Bay Scavenger Hunt!

Big on Bay is a fun event occurring in the Toronto downtown core on September 17th, 2026, at 5:00 pm for Big Brothers Big Sisters of Toronto Day to raise the much needed funds to support youth mentorship.

What we are doing:

Teams of 5 will engage in fun activities in and around Bay Street, helping to raise awareness of Big Brothers Big Sisters of Toronto and get the chance to win amazing prizes and bragging rights of being Big on Bay for team and individual challenges. The event will start and end at TMX Market Place (120 Adelaide St W), concluding with an after-party and award.

To participate, there is a registration fee of $20 per individual and $100 per team, and teams are expected to raise funds through peer-to-peer fundraising or general donations! With over 450 kids still on our waitlist, your participation helps us move one step closer to ensuring every child has the support they deserve.

Why participate:

Whether you are in the Bay street area or part of the BIG family or just a competitive individual, this event is bringing out people of all walks of life to raise funds for mentorship of youth in Toronto.

Get ready to make a BIG impact in a fun and meaningful way. Big Brothers Big Sisters of Toronto invites you to take part in our Big on Bay Social Scavenger Hunt — an exciting, team-based challenge powered by Social Scavenger.

For those looking to raise awareness of their business while supporting a charity with deeply impactful work, we have you covered. Please reach out to events.toronto@bigbrothersbigsisters.ca to learn more about sponsorship.

Are you ready to play for a purpose?

Siobhan Calderbank's Bio

Siobhan Calderbank is an award-winning keynote speaker, leadership strategist, and Talent & Human Resources Executive with more than 20 years of experience transforming organizations, building inclusive cultures, and developing diverse leadership pipelines. Currently serving as Vice President, Talent & Performance Management at Element Fleet Management, she is recognized for leading large-scale organizational transformation, advancing talent and leadership strategies, and helping organizations build high-performing, future-ready teams.

Recognizing the need for greater access to mentorship and leadership development, Siobhan is dedicated to empowering women and youth, particularly those from underrepresented communities, through coaching, career development, networking, financial aid, and leadership-building opportunities. Her commitment to creating pathways for others to succeed is reflected in her extensive mentorship, community leadership, and advocacy efforts focused on supporting youth, women, newcomers, and emerging leaders.

As a globally recognized speaker, Siobhan has inspired audiences from more than 70 countries through conferences, corporate events, and leadership forums. She is a published author and contributor featured alongside influential thought leaders including Oprah Winfrey, Maya Angelou, John Lewis, and Deepak Chopra. Her thought leadership on leadership, change management, inclusion, and talent development has been featured across numerous publications and media platforms. Her voice has been featured on ABC, CBS, NBC, FOX, and CW, and she has appeared on Reuters and Nasdaq billboards in Times Square, as well as Planet Hollywood in Las Vegas.

Siobhan has held several leadership and advisory roles supporting diversity, inclusion, mentorship, and community development initiatives. Her contributions have been recognized through numerous honours, including being named one of the Top 100 Accomplished Black Canadian Women, receiving the Women of Inspiration Award for Diversity and Inclusiveness, and being recognized as one of the Top 100 Black Women to Watch in Canada.

She holds a Master of Arts in Leadership from Royal Roads University, a Certificate in Advanced Human Resources from Queen’s University, and a Bachelor of Commerce in Information Technology Management from Toronto Metropolitan University. Through her professional leadership and community service, Siobhan remains committed to helping individuals realize their potential and creating opportunities that enable future generations to thrive.