2000s

2000 -

• 1st Year for Slap Shot Hockey and the Okoboji Underwater Search and Rescue Demo
• Chairpersons: Blain Andera and Sue Laue
• Cheerleaders: Brenda Dryer, Twyla Garnmeister, Margaret Northey, Andrea Schwarck, Jeff Schwarck, Toby Shine, Mike Stineman, Rick Wiersma

2001 -

• 1st year of the Little Sioux Off-Road Challenge.
• This was the 1st year that the RIDES bus transported people from event to event.
• Chairpersons: Blain Andera and Chad Schuchert
• Cheerleaders: Ruth Schwarck, Gene Reed, Bob Reed, Gloria Currell, Bob Curell, Edna Wattier, Carole Ayres, Emil Richter

2002 -

• Warm weather! New York Times was here and the University of Okoboji Winter Games made the 8th page article on 1/28/02.
• Extraveganza was moved to the Green Space now known as Preservation Plaza for the Bonfire and Fireworks Extravaganza due to ice condtions.
• Chairpersons: Chad Schuchert and Jeff Smith
• Cheerleaders: Molly Rohlfsen, Don Greagerson, Marge Gregerson, Alex DenHerder, Blain Andera, Darwin Pike, Larry Stoller, Bob Shaw

2003 -

• The Iowa Rock n Roll Musuem opens its doors.
• Hy-Vee sponsors a "Turkey Bowling" game
• Chairpersons: Jeff Smith and Terry Veldman
• Cheerleaders: Father James Bruch, Carole Caviness, Gary Caviness, Ann Ditsworth, June Goldman, Steve Schwaller, Greg Stevens, Ron Walker

2004 -

• Chairpersons: Terry Veldman and Randy Cornwall
• Cheerleaders: John Adams, Steve Anderson, Phyllis Kempema, Pat McGill, Cary Parker, Mike Peschon, Chad Schuchert, Barb Tagami

2005 -

• First year of the Texas Hold'em tournament and First year of the Red Hat Luncheon
• Chairpersons: Randy Cornwall and Abbey Larson-Heimensen
• Cheerleaders: Carla Beckendorf, Russ Beckendorf, Kevin Kuhlman, Abbey Larson-Heimensen, Gary Owen, Randy Rohlfsen, Jeff Smith, Brad Tifft

2006 -

• Chairpersons: Lance Evans and Abby Larson-Heimensen
• Cheerleaders: Wynette Moore, Larry Traughber, Phil Peterson, Wally Jorgensen, Lance Evans, Tracy Evans, Amanda Lippon, Audrey Kuhlman

2007 -

• Chairpersons: Lance Evans and Collin Heimensen
• Cheerleaders: Julie Fillenwarth, Joe VaderLaan, Erin Roe, Collin Heimensen, Mary Thunhorst, Terry Klein, Anitra Wolf, Matt Richter

2008 -

• 1st year of the ArtsLIVE People Project and Hill Ave. Indoor mini golf tournament
• Chairpersons: Lance Evans and Molly Gildemeister-Sorensen
• Cheerleaders: Dr. Steven Baskerville, Dr. Randy Cornwall, Tim Horsman, Mary Kennedy, Bill Maas, Greg Richards, Tom Tourville, and Gary Zeman

2009 -

• Grand Old Opre at the SAMI Center generated $12,000 for the Mini Wakan Shelter restoration. Also set a record for attendance!
• Chairpersons: Molly Gildemeister-Sorensen and John Adams Jr.
• Cheerleaders: John Adams Jr., Michelle Adams, Bill Eich, Janelle Holter, Dennis Lippon, Dave Rowley, Julie Scheib, Tonja Vanbee

2010 -

• Chairpersons: John Adams, Jr. and Janelle Holter
• Cheerleaders: Dan Delperdang, Brett Hetland, Jeff Knapp, Di Lorenzen, Joe Meyer, Bob Miller, Stacy Rosemore, Jane Shuttleworth
  

2011 -

• Chairpersons: Janelle Holter and Jeff Thee
• Cheerleaders: Kathy Lockey, Wayne Northey, Marty Spies, Denny Perry, Walt Homan, Beryl Marra, Jan Bowles, Steve Lindeberg
  

2112 -

• Chairpersons: Jeff Thee and Erin Roe
• Cheerleaders: TBD