Softball. Sunshine. Food. Good vibes. One awesome day.

Head Out Toronto organizes fun, social softball events in Toronto that support meaningful causes. Our goal is to bring people together to connect, get active, and give back to the community. While we’re focused on softball right now, we’re all about creating experiences that promote mental well-being and foster real connections.

You can register for our events directly through our website. Visit our Registration Page to sign up and secure your spot. Simply follow the instructions, complete the payment process, and get ready for a day of fun and connection! 

Our next tournament is happening on Sunday, May 18, 2025, at Coronation Park in Toronto. Join us from 11:00 AM to 6:30 PM for a full day of softball, fun, and community connection! 

The participation fee for our softball events ranges from $20 to $50 per person, depending on the specific event. All net proceeds are donated to our primary charity sponsor and partner charities, ensuring your contribution supports meaningful causes in impactful ways. 

No prior experience is needed! Our events are beginner-friendly and designed for players of all skill levels.  

Dress comfortably in athletic wear, similar to what you’d wear to the gym. We recommend sneakers or cleats for better traction on the field. If you have a softball glove, bring it along—but don’t worry if you don’t, as we’ll have gloves available for you to borrow. Don’t forget sunscreen, a water bottle, and your enthusiasm for a fun day on the field! 

Participants must be 16 years or older to play softball, but there’s no age requirement to join us and enjoy the event! Everyone is welcome to come out, cheer on the teams, and take part in the fun activities we have planned. 

The charities we support may vary with each event, but we plan to have a core set of five partner charities that consistently benefit from our donations. Past events have supported organizations like Free Korean Dogs and Toronto Cat Rescue. Visit our Charities section to learn more about the causes we champion and how your participation makes a difference! 

If you can’t attend the event, you can still make an impact! We encourage you to purchase a donation ticket through our registration page—your contribution will go directly toward supporting our partner charities but will not register you as a player. You can also learn more about our partner organizations and how to donate directly by visiting our Charities Page. Every contribution helps make a difference! 

Absolutely! We’re always looking for enthusiastic volunteers to help make our events a success. Visit our Volunteer Page or reach out to us on social media to learn more about available opportunities and how you can get involved. We’d love to have you on the team! 

We’d love to partner with your business as an event sponsor! Sponsorship is a fantastic way to connect with the community while supporting meaningful causes. To learn more, please visit our Vendor & Sponsorship Page for details and opportunities, or reach out directly to Derek at charitysoftballevents@gmail.com or (905) 580-6638. Let’s make a difference together! 

Teams are organized before the event to ensure a fun and competitive experience for everyone, with a balanced mix of skill levels. If you’d like to be on the same team as a friend or group, please let us know during the registration process. If you need to update your request later, feel free to reach out, and we’ll do our best to accommodate you! 

Our upcoming tournament on May 18th will feature eight teams competing in a fun and friendly tournament-style format. Each team will play 2–3 games, with a schedule designed to ensure plenty of action and excitement for all participants. 

Yes, basic rules and guidelines will be shared at the beginning of the event to ensure everyone has a fun and safe experience. Our games follow a friendly, recreational format with an emphasis on inclusivity and enjoyment. For more details, you can review the full game rules here.