Leagues at Dill Dinkers - Columbia, MD

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WELCOME TO SILLY PICKLES!

We run the world’s funnest pickleball leagues, designed to make playing simple, social, and full of serious funzies!

Whether you’re brand new to the game or already own 3 paddles, our ladder league format makes sure you’re always playing at your level.

Join solo or with friends! Either way, you'll play as an individual and rotate partners each week 🚀 Move up or down the rankings based on performance - creating the perfect mix of friendly competition and connection!

LEAGUE DETAILS

  • Regular Season Play

    Most seasons run 6–8 weeks. Find dates, and times listed on each league page, depending on your season!

  • Our Ladder Format

    Each week, you’ll play within a new group of 4 people for one hour at your skill level.

    If you come solo, expect to leave with friends - you'll play each game with a new partner!

  • Easy Scheduling

    If you need to miss a week, no problem! 📅 Just use our weekly RSVP to let us know.

    Need a sub? Just click through our system to request one.

  • Weekly Re-Ranking

    Submit your points after each set of games.

    We’ll use your scores to update your ranking, so matchups are fun and accurate every week!

  • All Skill Levels Welcome

    Our ladder format means leagues can accommodate all skill levels (whether you're way better, or way worser than everyone 🤪).

    Everyone is welcome, whether you’ve never played or are more advanced!

  • Social and Happy Hours

    Every league has their own happy hours and socials throughout! 🍻

    Welcome to the world's funnest league...on and off the courts.

LEAGUE FAQS

Do I need previous league experience to join?

Nope! All of our leagues include a beginner intro session, so we'll teach you the basics!

Most players are newer to pickleball, and our league generally, so you'll fit right in! Our ladder structure always keeps you playing at your level, even if you get really good, really quick 😉
Can I request to play with a friend?

Our leagues are intentionally designed for social play, so we can't guarantee that you'll be placed with your friend during games.

You may end up on the same courts if you're the same level, or come early / hang late with them to socialize!
How does the ladder format work?

Each week, you’ll be placed in a group with players close to your skill level. You’ll play mini games to 15, rotating partners each round.

When you’re done, submit your scores. From there, you'll either stay in your current group or move up / down the ladder for the following week.
Do you offer refunds if my schedule changes?

Before the league starts, we can definitely work something out! We know life happens. We are not able to provide refunds for individual nights missed.

If Silly Pickles need to reschedule for a week for weather or a facility-specific event, we'll let you know ahead of time and either have a make up session, or refund you for that game day!
Do I need to know all the rules before playing?

Not at all! We also offer intro sessions for new players who want a quick walkthrough before jumping into league play. Pickleball rules are easy to pick up as you play, and our hosts are always happy to help with questions.
Can I stay and hang out after my session?

Definitely! Half of our fun happens off the courts. Many of the venues we play at have social areas where players like to gather before and after matches.

Grab a drink or a quick snack, relax, and stick around to watch other games. We'll also have some planned league get togethers for you! Check your group chat for an invite!