2027 Wellness Challenge Planning Calendar
Plan a Year of Wellness That Fits Your Organization
The best wellness programs don’t try to keep employees engaged every week of the year. Instead, they create a few well-timed opportunities that bring people together, help them experience success, and build lasting habits.
Whether you’re planning 1 signature event, 2 seasonal challenges, or 3 campaigns spread across the year, this calendar can help. It groups wellness challenges by season, making it easy to build an annual wellness strategy that fits your goals, your organization, and the natural rhythm of the year.
Use it as a starting point, mix and match ideas, and adapt the timing to your organization.
If you’re planning…
1 challenge
2 challenges
3 challenges
Recommended Approach
Choose 1 signature event. Walktober is the most popular choice.
Pair a spring or winter challenge with Walktober in the fall.
Choose 1 challenge in winter, 1 in spring or summer, and Walktober in the fall.
Recommended Approach
If you’re planning 1 challenge…
Choose 1 signature event. Walktober is the most popular choice.
If you’re planning 2 challenges…
Pair a spring or winter challenge with Walktober in the fall.
If you’re planning 3 challenges…
Choose 1 challenge in winter, 1 in spring or summer, and Walktober in the fall.
Q1: January-March
Help employees turn New Year’s motivation into meaningful progress. Focus on simple, encouraging experiences that build confidence and healthy habits throughout the year.
Builds momentum by helping employees establish lasting physical activity habits.
Keeps healthy habits on track during the winter months with a fun, engaging experience.
Strengthens emotional well-being through activities that build resilience, confidence, and stronger relationships.
Encourages healthier eating through simple, personalized activities that fit everyday life.
Q2: April-June
Take advantage of warmer weather and renewed energy. Encourage employees to get outside, stay active, and build momentum before summer arrives.
Celebrates spring by inspiring employees to enjoy the season and build healthy habits one step at a time.
Combines movement with music and nostalgia, turning physical activity into a fun, shared experience.
Turns time outdoors into a chance to slow down, notice nature, and enjoy being active.
Turns healthy habits into a journey around the world, with new destinations to discover along the way.
Q3: July-September
Help employees maintain healthy momentum through the busy summer months. Encourage them to stay connected as they head into fall with renewed energy.
Captures the fun and nostalgia of summer with activities that make well-being feel like part of the season.
Turns physical activity into an intergalactic adventure employees can experience together.
Makes nutritious eating more inviting by encouraging employees to add more color to every meal.
Encourages simple daily actions that help employees feel more energized and less stressed.
Q4: October-December
Finish the year strong by celebrating progress and strengthening workplace connections. Bring employees together to recognize accomplishments.
Inspires employees of all activity levels to walk more while sharing the experience with coworkers.
Builds financial confidence through practical activities that support healthier money habits.
Helps employees enjoy the holiday season while maintaining healthy routines and realistic balance.
Encourages gratitude, kindness, and meaningful connections that strengthen workplace relationships.
Ready to build your annual wellness calendar?
Your HES account manager can help you choose the right mix of challenges and provide the planning resources you need to make each one a success. Schedule a quick call to discuss your options and receive a no-obligation estimate for your population.
FAQs
How many employee wellness challenges should we offer each year?
Most organizations get the greatest benefit from 2-3 wellness challenges each year. Running more can lead to challenge fatigue for both participants and wellness teams.
How do I choose the right wellness challenge for my organization?
Start with your organization’s wellness goals, then choose challenges that support them. Physical activity challenges are consistently the most popular because they support physical, mental, and emotional well-being.
How long should a wellness challenge last?
Most HES wellness challenges are available in 4-, 6-, and 8-week formats. 4 weeks works well for introducing a new challenge, while 6-8 weeks gives employees more time to build habits and engage with coworkers.
When is the best time to run a wellness challenge?
Timing is less important than choosing a great challenge and executing it well. Aim for 2-3 times each year that you can repeat consistently so employees come to expect and look forward to them.
Should we repeat the same challenge every year or try something new?
Many HES clients make Walktober their annual fall tradition, then add 1 or 2 different challenges during the rest of the year. That combination provides a familiar favorite while keeping the program fresh.
Can we customize the timing to fit our organization?
Yes. HES wellness challenges range from 4-8 weeks, and most aren’t tied to a specific season or event. Your HES account manager can recommend options that fit your goals and schedule.
Should we offer incentives to get good participation?
Not necessarily. While incentives can increase participation, they’re often less important than choosing a challenge employees genuinely enjoy and making it easy to join. Many organizations achieve strong participation in HES wellness challenges with little or no incentive because the experience itself is engaging, social, and well promoted. If you do offer incentives, keep them simple and use them to reinforce participation — not as the primary reason people join.