Upcoming Events
Join us for the next gatherings from Different Strokes Pickleball Group. From a glow-in-the-dark Halloween bash to a community Wellness Day, there’s something for every player. Grab a friend, mark your calendar, and come be part of the fun.
Pickle Boo: Glow in the Dark Bash
A spooky, adults-only night of pickleball on Friday, October 23, from 6:00 to 9:00 PM at ChiPickle (1900 South Wabash, Chicago). Dink, drink, socialize, and show off your costume, with pizza and snacks and prizes for the top two costumes. $15 per person with Zelle payment by 10/22, or $20 at the door.
Wellness Day
Join us Friday, November 13, 2026, from 10:00 AM to 3:00 PM at XS Tennis for a day of health and community. Enjoy pickleball and line dance instruction, blood pressure checks with Doctor Dora Dixie, special guests from Atlanta, and a Humana team member on site to answer Medicare questions. T-shirts and food provided, and all are welcome.
Past Events
Take a look back at the gatherings that brought our pickleball community together. From community celebrations to regional challenges, these events show what Different Strokes is all about: connection, joy, and great pickleball.
Legends of Pickleball
A celebration of our community leaders on Saturday, May 30, 2026, at Grand Crossing (7655 South Ingleside, Chicago). Enjoy open play and refreshments, then join us for the awards ceremony at 12:00 noon honoring the people who grow the game on and off the court.
Divine Nine Clinic
A free, beginner-friendly day at Jackson Park on July 12, from 2:00 to 6:00 PM. Open to seniors 50+, pre-seniors, and young adults, with beginner clinics, open play, an optional D9 team challenge, and music. No experience needed.
Best of the Mid-West Pickleball Challenge
A friendly regional challenge on March 7 at Northville Pickleball Club in Michigan, where Different Strokes (Chicago) teamed up with Black Ace Pickleball (Metro Detroit) and Ohio Players Pickleball. Warm-up started at 1:30 PM and the challenge at 2:00 PM, followed by dinner at 6:00 PM.