Working Well’s New & Improved Annual Corporate Cup Challenge
Saturday, November 7, 2026
Apalachee Regional Park
Get your team together. Get outside. Get moving. Get ready to have FUN!
The Corporate Cup Challenge is back—and it’s bigger, better, and more inclusive than ever! Every fall, co-workers come together for a one-of-a-kind day of fitness, teamwork, friendly competition, and FUN. This year, Working Well has made some big changes to make the Corporate Cup Challenge more accessible, more exciting, and more fun for everyone. So, gather your coworkers, build your team, and get ready to compete for the Corporate Cup—the ultimate trophy for teamwork, fitness, and team spirit! And you don’t have to compete to be part of the fun. Family, friends, and pets are invited to come cheer on the teams!
BIG CHANGES THIS YEAR!
We’ve revamped the Corporate Cup Challenge to make it:
- MORE INCLUSIVE.
- MORE FUN.
- MORE WAYS TO GET INVOLVED.
Whether you’re a runner (beginner or veteran), team-building enthusiast, Office Olympics champion in the making, Wellness Warrior, or the person who shows up to cheer everyone else on—there’s a place for YOU at this year’s Corporate Cup Challenge!
The Challenge
There are multiple ways to participate, so bring your strengths, your sense of humor, and your team spirit! Here’s the event lineup:
8:00 a.m. — Check In: Get your team checked in and ready to go!
8:30 a.m. — 1-Mile Fun Run: Grab your coworkers, family, children, and friends to kick off the day with a fun run together. All ages are welcome in the fun run!
8:45 a.m. — 5K(ish) Run: It’s a 5K-ish challenge—because we’re here to have fun, not take ourselves too seriously!
9:30 a.m. — Office Olympics: Teams of 2 compete in a series of hilarious, creative, and surprisingly challenging office-inspired events.
10:15 a.m. — Wellness Warrior Challenge: Teams of 2 put their strength, speed, agility, coordination, and teamwork to the test.
11:00 a.m. — Awards: Celebrate the teams, the accomplishments, the spirit, and the FUN!
Go for the Corporate Cup!
Want your organization to take home the coveted Corporate Cup? Here’s what it takes:
Your organization must have at least one registered participant or team in every event:
- 1-Mile Fun Run
- 5K(ish) Run
- Office Olympics
- Wellness Warrior Challenge
- AND your organization must have the fastest Wellness Warrior Challenge time among the competing teams.
It’s not just about being fast or agile or strong. It’s about showing up, getting involved, supporting your coworkers, and bringing your team spirit!
Office Olympics
Think your team of 2 has what it takes to tackle some office-related activities? Get ready for a series of fun, fast-paced challenges designed to test your focus, coordination, creativity, teamwork, and ability to laugh at yourself.
Activities may include silliness such as:
- Coffee Cup Maze: Navigate a maze while carrying a cup of coffee—blindfolded and guided by your teammate!
- Rubber Band Ball Race: Get up, get moving, and get that rubber band ball across the finish line.
- Cup Stack Attack: Stack ’em up! Teamwork makes the dream work.
- Office Junk in the Trunk: Shake, wiggle, and move those office supplies out of the box.
- Paper Clip Link-Up: Link it up with your teammate—and do it fast!
- Toilet Paper Hike: A little teamwork, a little athleticism, and maybe a touchdown dance or two.
Bottom line: The Office Olympics is where workplace skills meet ridiculous amounts of FUN!
Wellness Warrior Challenge
Ready to unleash your inner Wellness Warrior? This fast-paced challenge is made for teams of 2 and combines strength, speed, agility, endurance, coordination—and plenty of team spirit!
Warrior activities may include challenges such as:
- Tire Carry & Drag
- Tire Flip & Roll
- Army Crawl
- Down & Back Dashes
- Fence Over/Under
- Sprint to the Finish Line
You’ll work together, push yourself, cheer each other on, and have a blast doing it. And remember: the fastest Wellness Warrior Challenge time could help your organization claim the coveted Corporate Cup!
It’s More Than a Competition
The Corporate Cup Challenge is about getting you out of the office, away from your desk, and into the sunshine and fresh air. It’s about building relationships with your coworkers, getting active, trying something new, laughing together, and creating memories outside the workplace. Build teamwork. Get active. Have fun! Friends, family, and well-behaved leashed pets are welcome. Come compete, participate, or simply cheer on your favorite team.
Here’s How it Works:
Option 1: Form one or more Company Teams (the most fun option that gives your workforce a healthy dose of team-building and wellness!)
- Recruit up to 8 employees to join your team.
- Choose a fun team name. (no extra points for creativity, but it sure does add to the fun!)
- Your up to 8 team members include:
- Up to 3 runners for 5K(ish) Run,
- A 2-member pair for the Office Olympics,
- A 2-member pair for the Wellness Warrior Challenge, and
- At least one participant in the 1-Mile Fun Run.
In order to be eligible for the Overall CCC Trophy, your Company Team must include at least one registered participant/pair in each of the above activities.
Option 2: Grab a partner to form a 2-person team for either the Office Olympics or Wellness Warrior Challenge.
Option 3: Go solo in the 1-Mile Fun Run (free and open to all ages) and/or the 5K(ish) Run.
Pricing/Registration
Early-bird Deadline: Tuesday, October 27 at 5:00 PM
Company Teams: Includes registration for up to 8 employees: Up to 3 runners for 5K(ish) Run + 2-member team for Office Olympics + 2-member team for Wellness Warrior Challenge + 1 Fun Run participant – also eligible for Overall CCC Trophy!
- $100/team: WORKING WELL MEMBERS until early-bird deadline
- $125/team: NON-MEMBERS until early-bird deadline
- $150/team: All registrants AFTER early-bird deadline
Office Olympics or Wellness Warrior Challenge as Single Events: Includes registration for 2-member team entry in Office Olympics, OR 2-member team entry in Wellness Warrior Challenge
- $35: WORKING WELL MEMBERS until early-bird deadline
- $40: NON-MEMBERS until early-bird deadline
- $45: All registrants AFTER early-bird deadline
5K(ish) Run as a Single Event: Includes registration for single entry in 5K(ish) Run
- $15: WORKING WELL MEMBERS until early-bird deadline
- $20: NON-MEMBERS until early-bird deadline
- $25: All registrants AFTER early-bird deadline
Fun Run: Free! All ages welcome.
Don’t Wait—Get Your Team Registered!
This is your chance to turn a group of coworkers into a team. Pick your teammates. Choose your events. Bring your competitive spirit. Invite your family and friends. And get ready for a day you’ll be talking about long after the awards are handed out. The Corporate Cup is waiting for you. REGISTER TODAY!
Thank you to our generous SPONSORS!
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Awards
The Corporate Cup Trophy
The Corporate Cup winning team gets the big, beautiful trophy that passes from winner to winner each year. This team must consist of employees and their dependents from a single company/business! This award is given in the true CCC spirit — coworkers coming together to represent their organizations as part of their wellness programs. The trophy winner must have at least one participant in each of the events — Family Fun Run, 5K(ish) Run, Office Olympics, and Wellness Warrior Challenge — AND have the fastest Warrior Challenge time of the competing teams.
Additional awards:
- Spirit Award earned by the company with the greatest number of supporters who come out to cheer on their team and sign in on their company’s sheet.
- Awards for Top 3 5K(ish) finishers
- Finisher medals for 5K(ish) Run
- Finisher bandanas for Office Olympics and Wellness Warrior Challenge