May is National Walking Month, Mental Health Awareness Month, and National Bike Month all at once. If your group needs a reason to take care of their wellbeing, May hands you (at least) three. 

Below are 10 ready-to-launch challenge templates, complete with challenge modes, duration recommendations, prize ideas, and chat prompts. Pick one and run it as is, or mix and match, stack, and make them your own.

10 May Challenges for Every Type of Mover

Theme: May-rathon Virtual Race 🏅

Suggested Duration: 1 month

Challenge Mode: Virtual Race (85 miles), “Race to the Finish Line” map theme

Challenge Name Ideas:

• "May-rathon"
• "Sunny Strides Challenge"
• "The May Mile Challenge"

Description: You don't have to run a marathon to do a May-rathon. Cover 85 miles over the month on our Race to the Finish Line map. Every walk, run, or ride moves you forward.

Prize Ideas: Participants who finish the virtual race are entered to win:

• Ice Barrel 300 (upright, sleek, fully insulated cold therapy tool for daily recovery)
• Normatec Elite Hips (cordless compression device that relieves hip tightness, IT band pain, and lower back tension)
• SMARTSTEP™ System (dual-purpose cardio and strength step platform for taking your training beyond steps)

Theme: May Momentum Streak Challenge 🔄

Suggested Duration: 31 days

Challenge Mode: Streak (personalized goal, 10 to 45 active minutes/day)

Challenge Name Ideas:

• "Move Every Day in May"
• "May Momentum Challenge"
• "Mighty May Streak"

Description: It’s time to build some momentum! Pick a daily active minutes target that fits your life and hit it every day. Personalized goals mean the bar is yours to set. The only rule is you don't skip a day.

Prize Ideas: Full-month streak completers enter to win:

• Vyper 3 (high-powered vibrating foam roller with three intensity levels)
• Compression Boots (compression technology that makes your legs feel fresh again)
• PEMF Pro Mat Starter Kit (complete kit with pro mat, organic cotton cover, towel topper, bath soak, and cleaner)

Theme: Mother's Day Dedication Challenge 💐

Suggested Duration: 7 to 14 days (leading up to Mother's Day, second Sunday of May)

Challenge Mode: Individual Target (75,000 steps)

Challenge Name Ideas:

• "Miles for Mom"
• "Walk for the Ones Who Showed Up"
• "The Mother of All Challenges"

Description: Dedicate this challenge to someone who raised you, shaped you, or just kept you from total chaos. Every kind of mother figure counts. Hit 75,000 steps before Mother's Day and let your movement be the tribute. 

Prize Ideas: Hit the target and enter to win a gift for mom:

• Face Cupping Kit (silicone face cups that lift, sculpt, and depuff while reducing tension and puffiness)
• Acupressure Neck Wedge (wedge-shaped pillow that relieves neck tension and tech neck in minutes)
• ClassPass Membership (access to thousands of top-rated gyms, fitness studios, salons, and spas worldwide)

Theme: May Team Step Showdown 🏆

Suggested Duration: 2 weeks

Challenge Mode: Team Leaderboard

Challenge Name Ideas:

• "May Madness Challenge"
• "Stride Squad Showdown"
• "Stepping Up in May"

Description: Two weeks, one leaderboard, may the best team win. Your team's ranking is based on average steps, so a team of 3 can beat a team of 10 if they're outworking them daily. Check where you stand, check where they stand, and close the gap. Bonus points for the most creative name!

Prize Ideas: The winning team celebrates with one of these:

• Hypervolt 2 Pro (powerful percussion therapy with 5 speeds and an ultra-quiet motor)
• The Kettleball (all-in-one total-body training tool reimagined from the gym classic)
• Rogue Color Medicine Balls (durable vinyl medicine ball in 11 weight options for functional training)

Theme: Active Commute Challenge 🚲

Suggested Duration: 5 to 7 days

Challenge Mode: Target (25 miles) or Freestyle (log each active commute)

Challenge Name Ideas:

• "Commute & Conquer"
• "Pedal, Stride, Repeat"
• "Walk Your Way to Work"

Description: This challenge opens it up to any kind of active travel: cycling, walking, running, or rolling. Log your active commutes across the week and see how far you can travel without a car. The goal is 25 miles over the week, that's 3–5 miles a day, depending on how many days you go. 

Prize Ideas: Everyone who hits their distance target or logs five active commutes enters to win:

• Ora Athletic Slide (HOKA recovery slide with plush dual-density cushioning for post-commute comfort)
• Bala Bangles (viral wrist and ankle weights that add resistance without the bulk)
• SHAPES Bundle 2.0 (3 high-quality fabric resistance bands plus sliders for anywhere workouts)

Theme: Walk the World Group Virtual Race 🌍

Suggested Duration: 1 month

Challenge Mode: Group Virtual Race (10,000 miles), “International Globetrot” map theme

Challenge Name Ideas:

• "Walk the World in May"
• "May Miles Collective"
• "Global Stride Challenge"

Description: This month, the goal is 10,000 miles and every step you log moves the whole crew further along the International Globetrot map. Journey through South and Central America, the United States, Europe, Africa, the Middle East, and Asia, unlocking new destinations as the miles add up.

Prize Ideas: When the group crosses the finish line, three of the top 20 participants win:

• WHOOP LIFE (premium WHOOP membership with medical-grade ECG capabilities and the most advanced longevity insights)
• Recovery Pod (full-body compression system for deep muscle recovery after a big month)
• Full Body Intelligence™ Test (Viome at-home test with 50+ health scores covering gut, oral, and cellular health)

Theme: Spring Finale Group Challenge 🎯

Suggested Duration: 2 weeks (end of May)

Challenge Mode: Group Target (5,000,000 steps)

Challenge Name Ideas:

• "Strong to the Finish"
• "Spring Sprint to Summer"
• "May All-Out Challenge"

Description: Two weeks left in spring. The goal is 5 million steps as a group. Log yours, watch the total climb, and let’s finish the season strong.

Prize Ideas: When the group hits the target, three participants win:

• Ice Barrel 500 (premium cold therapy barrel with built-in steps, a seat, and full insulation)
• Clifton 10 (HOKA's lightweight daily trainer with plush, featherlight cushioning)
• New Balance 9060 Sneakers (retro-inspired chunky sneakers with Y2K vibes and modern cushioning)
• Bala Beam (sculptural 36" weighted barbell wrapped in baby-soft silicone)

Theme: National Walking Month Challenge 🚶

Suggested Duration: 1 month

Challenge Mode: Target (200,000 steps), Group Target (20,000,000 steps)

Challenge Name Ideas:

• "May the Steps Be With You"
• "Walk This May"
• "200K This May"

Description: There's no better way to celebrate National Walking Month than with a month-long step challenge. Walking is one of the easiest ways to boost your mood, improve your health, and get outside, so we're challenging you to walk at least 200,000 steps this May and hit a group target of 20 million steps together. That breaks down to about 6,500 steps a day if 100 people join, but you don't have to be perfect. Move at your own pace and show us how you'll walk this May.

Prize Ideas: Hit the target and be entered into a raffle for one of these walking essentials:

• HOKA Bondi 9 (max-cushioned walking shoe for cloud-like comfort)
• Stride-6 (Echelon treadmill for walking rain or shine)
• G-Vest Icon 10 lb (weighted vest to level up your daily walks)

Theme: National Bike Month Challenge 🚴

Suggested Duration: 1 month

Challenge Mode: Target (100 miles)

Challenge Name Ideas:

• "Ride & Stride Challenge"
• "Spin into Spring"
• "Miles for May"

Description: Celebrate National Bike Month by spinning into spring. Throughout May, riders will work toward an individual goal of 100 total miles. Ride at your own pace, whenever you can, wherever you can. Mix in a walk or run if you prefer, whatever it takes to hit that target.

Prize Ideas: Hit the target and be entered to win one of these:

• Hypervolt Go 2 (compact massage gun to soothe your muscles after a long ride)
• CastleFlexx Sport (portable stretching device for post-ride recovery)
• Matcha Latte (ready-to-drink matcha latte for clean pre-ride energy)

Theme: Mental Health Awareness Month Challenge 🧠

Suggested Duration: 1 month OR 2-week sprint

Challenge Mode: Stick To It (30 active minutes, 10x/month) + Freestyle (5-minute meditation, 10x/month)

Challenge Name Ideas:

• "Mindful Miles"
• "Step Into Mindfulness"
• "Move for Your Mind"

Description: Exercise has been shown to improve mental health, and since May is Mental Health Awareness Month, we're challenging you to complete 30 minutes of activity and 5 minutes of meditation at least 10 times each this month. See how many days you can reach your goal, and remember: it's about progress, not perfection.

Prize Ideas: Complete both your activity and meditation goals and be entered to win one of these:

• Alpha BRAIN® (supplement for cognitive function, memory, and focus)
• Lion's Mane Mushroom Gummies (brain-boosting mushroom gummies)
• Kin Lightwave (non-alcoholic functional beverage to help balance stress responses)

Keep the Momentum Going Into Summer

May is a good month to close out spring with something your group will remember. Run one challenge, stack two, or save a few of these for June. They'll still be here.

👉 Want to keep it going? Browse the Annual Fitness Challenge Calendar for ideas across all 12 months, explore all Stridekick challenge modes, or check out all the virtual race maps if you want to take your group somewhere new.

Happy Stepping 👟