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Welcome to PickleMeSilly

PICKLEBALL FUN FOR EVERYONE!

PickleMeSilly specializes in creating and managing Pickleball tournaments, leagues, events, and unique Pickleball products.

PICKLEBALL COACHING TIPS VIDEOS

Learn Skills from the Pros!

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The Next PickleMeSilly Event!

September 20 & 21, 2025

Cockeysville, Maryland

Join us as we team up with the Cockeysville Dill Dinkers to celebrate their first anniversary. A week-long celebration will culminate in a two-day competitive tournament managed by PickleMeSilly. Registration is scheduled to open on July 25.

Signature PickleMeSilly Tournaments & Events Schedule

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St. Patrick's Day Pickleball Tournament

SEE YOU AGAIN IN 2026!

Finksburg, Maryland - Completed 

Our second annual St. Patrick's Day Tournament will take place in Spring of 2026. Good cheer and the promise of gold at the end of the rainbow will bring out the best players! See you there!

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Blue Hawaii Pickleball Tournament

SEE YOU AGAIN IN 2026!

Finksburg, Maryland

The first annual event was an awesome fun time and we will be back in 2026!

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Memorial Day Pickleball Tournament

SEE YOU AGAIN IN 2026!

Location is to be determined.

The first and original signature PickleMeSilly tournament since 2023, the Memorial Day Tournament ushers in the summer Pickleball season. Stay tuned for news in 2026!

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Holiday Spectacular Pickleball Tournament

December 13-14, 2025

Finksburg, Maryland

Mark your calendars for our third annual holiday season Pickleball tournament. Get in the holiday spirit by playing some fun competitive Pickleball and earn chances to take home some awesome holiday prizes. See you there! 

Thank you to our sponsors!

Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
Pickleball Tournaments and Events in Maryland
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