Our 2026 Event Schedule is Announced- Save the dates!
BOOM! WIN ME!
New in 2026 - More play, More prizes, More VALUE!
- PLAY AND EARN CHANCES TO WIN A JOOLA BEN JOHNS HYPERION V PADDLE! Winner drawn 12/23/2026.
- Tournaments feature 8 team brackets with 7 GAMES MINIMUM.
- Registration includes first event. (A $5 per event is added from Pickleball.com)
- First 100 registered players receive gift for participation.
- Medals awarded to 1st, 2nd, 3rd place teams.
- Top 4 finishers in each bracket earn one entry per player for the 2026 paddle drawing.
- Players who play in all PickleMeSilly events in 2026 earn 5 entries for the 2026 paddle drawing.
2026 PickleMeSilly
Tournament Schedule
St. Patrick's Day Pickleball Tournament
March 21-22, 2026
Dill Dinkers - Finksburg, Maryland
Memorial Day Pickleball Tournament
THIS EVENT HAS BEEN CANCELLED
Another fun day completed and into the history books! Thank you to all who joined us this year check out the photos in the gallery!
See you all next year!
Blue Hawaii Pickleball Tournament
July 24-25, 2026
Dill Dinkers - Finksburg, Maryland
Holiday Spectacular Pickleball Tournament
December 5-6 2025
Dill Dinkers - Finksburg, Maryland
The inaugural event in 2025 was an awesome fun time, and we will be back in 2026 bigger and better! This Hawaiian themed event features fun treats and lots of Pickleball fun. Dig through the closet for your favorite Hawaiian shirt, and wear on the courts for chances to win prizes. Get that Hawaiian groove going with us this summer!
Mark your calendars for our fourth annual holiday season Pickleball tournament. This event is becoming an annual tradition to spread holiday cheer with all of our Pickleball friends. Join us and get in the holiday spirit by playing some fun competitive Pickleball and earn chances for holiday gifts. See you there!
Thank you to our sponsors!
