Events

A free annual event for all registered players ages 4-8 as well as families interested in joining the league — open to Learn to Play, T-Ball, and Rookie Ball divisions, and the general public. Skills stations for players, plus a chance to meet the Board and Executive Committee and learn about coaching, volunteering, and the Whitecaps program.

Our most important event of the year for transparency, community feedback, and shaping the future of the league. Open to all members registered in a paid program during the current or immediately preceding season. This year's agenda includes a season review, financial report, and future planning for the upcoming summer and beyond.

One of the year's most exciting traditions — the day the baseball family comes together to deliver or collect equipment across Oakville's parks and diamonds. Spring Truck Day loads the equipment trucks and disperses to diamonds; Fall Truck Day collects equipment back to the Cornwall Clubhouse for winter storage. Wraps up with a pizza lunch. Email volunteer@oakvillelittleleague.com to help — adults, high schoolers earning volunteer hours, and families are all welcome.

A league-wide event where every player receives a professional individual portrait and a custom-composed team photo. Arrive in full uniform (running shoes only — no cleats inside the community centre), 15 minutes ahead of your team's scheduled time slot. No scheduled make-up dates. A raffle supporting the Senior League Canada Region Championship runs alongside the event.

Every year, Oakville Little League organizes a group outing to a Toronto Blue Jays game — a great opportunity for teams to rally together, and a fun day out for the whole family. The league reserves a large block of tickets sold on a first-come basis through TeamSnap.

Oakville Little League hosts a local qualifier for the MLB Pitch, Hit & Run event — a free skills competition for boys and girls in age-based divisions (7-8, 9-10, 11-12, 13-14). Top performers can advance through a Team Championship at Rogers Centre and on to the National Finals at the MLB World Series.