Event Details
29th Annual LWSP Softball Tournament
August 7–9, 2026 | Lions Sports Park, 77 Thompson Road South, Milton
The LWSP Tournament returns for its 29th year—and this will be one of our biggest weekends yet!
More than 700 players across 54 teams—20 competitive and 34 fun-division teams—will take the field throughout the weekend. With approximately 2,000 players, families, friends and community members expected to join us, Lions Sports Park will be filled with great softball, live entertainment and the unmistakable LWSP atmosphere.
Weekend Highlights
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Softball games running throughout the weekend
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Fantastic raffle prizes
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Live music and entertainment
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Home Run Derby at 8:00 p.m. Saturday
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Expanded bar with more drink options and convenient tap payment
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Food and refreshments served by the U15 AHL Milton Winterhawks, supporting their team fundraiser
Live Entertainment
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Friday, August 7: Raquel’s Riot — 9:00 p.m.–1:00 a.m.
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Saturday, August 8: DJ 9 — 9:00 p.m.–1:00 a.m.
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Sunday, August 9: Camryn — 1:00–4:00 p.m.
This Year’s BBQ
This year’s LWSP BBQ is being held in loving memory of our dear friend Greg Demmery. All proceeds from the 2026 BBQ will be donated directly to Greg’s family.
Let’s show this incredible family what the Milton community is all about.
Location and Parking
Lions Sports Park
77 Thompson Road South
Milton, Ontario
Please note that the parking lot directly in front of the ball diamonds will be blocked off for the tournament. Guests should allow extra time to park and follow all posted signs and directions from tournament volunteers.
Come for the softball and stay for the music, food, raffles and community. We can’t wait to welcome everyone to the 29th Annual LWSP Tournament!
Fun Vs Competitive
Division Details – Know What You’re Signing Up For!
Fun Division
This division is all about good vibes, laughs, and a laid-back weekend of ball. Games take place Friday and Saturday only at Beatty Park and Lions Sports Park. Teams are expected to umpire their own games, and the focus is on enjoying the game, meeting new people, and supporting a great cause. No games on Sunday — just time to relax, cheer, and enjoy the finals!
Competitive Division
Ready to bring the heat? The Competitive Division is for teams looking for intense gameplay and a shot at the championship. Games run Saturday at Drumquin, Beatty Park, and Lions, with Sunday playoffs and finals at Lions Sports Park. This division includes official umpires for every game and ends with the LWSP Championship Game on Sunday.
Choose your level, bring your team, and swing for a cause!
Home Run Derby
Home Run Derby – Saturday at 8 PM on Lions 1
Step into the batter’s box and swing for glory at the LWSP Home Run Derby, happening Saturday, August 8th at 8:00 PM on Lions 1!
🏆 $20 entry fee
Women and Mens Division
Max 40 people
🕖 Sign up at the bar by 7:00 PM
⏱️ You’ll have 45 seconds to hit as many home runs as you can
Crush it out of the park for prizes, bragging rights, and the loudest cheers of the weekend. Whether you're hitting or watching, this is a must-see Saturday night showdown!
How many can you launch in 45 seconds? Let’s find out.