2026 Wellness Challenge Planning Calendar
Plan Your Year of Wellness Challenges: Engage, Motivate, and Inspire
Creating a healthier, more connected workplace doesn’t happen by accident — it’s the result of thoughtful organizing and consistent, engaging activities. Our 2026 Wellness Challenge Planning Calendar helps HR leaders, wellness coordinators, and benefits consultants map out fun, goal-driven campaigns that keep employees motivated all year long.
Each month highlights timely challenge ideas and wellness observances you can use to spark participation and connect to topics employees already care about — from physical activity and nutrition to mental health and financial well-being. Whether you’re launching your first program or refreshing an established one, this calendar provides a clear, ready-to-use framework to make 2026 your most impactful wellness year yet.
How to Use the 2026 Wellness Challenge Planning Calendar
Start With Your Goals
Decide what success looks like for your wellness program… boosting daily movement, reducing stress, improving nutrition, strengthening team connection. Choose challenges that align with these objectives.
Hint: Most HES challenges cover multiple goals.
Leverage Seasonal Relevance
Link your wellness activities to national health observances, holidays, or seasonal interests for higher engagement.
Examples: a heart-health step challenge in February or hydration focus in summer.
Mix It Up
Offer different choices — physical activity, mental/emotional well-being, nutrition, financial health — to keep participation fresh and inclusive.
Tip: Having a variety of challenges strengthens personal engagement as well as shared experiences.
Customize for Your Culture
Tailor themes and formats to fit your organization’s personality. Add competitions, milestone rewards, or department leaderboards for extra motivation.
Read more: See how Jefferson County combines HES challenges with their own wellness programming.
Promote and Celebrate
Use email, intranet, posters, and team meetings to build anticipation. Recognize achievements and share success stories to keep momentum high.
Results: SVVSD keeps participation strong year after year.
Though this calendar offers planning suggestions, HES programs can be implemented any time. Your account manager can help pick the best challenge and timing for your organization.
MONTH
CHALLENGE
OBSERVANCES
PLANNING TIP
JAN
Alternatives:
Right On the Money
Snow Wonder
New Year’s Resolutions Week
(January 1-7)
Kick off the year with a fresh start — combine movement with financial wellness tips to tap into resolution energy.
FEB
Alternatives:
10K-A-Day
Colorful Choices
Random Acts of Kindness Week (February 14-20)
American Heart Month
Pair health goals with acts of kindness for a well-rounded wellness boost.
MAR
Alternatives:
Colorful Choices
Good Nurtured
World Compliment Day (March 1)
National Sleep Awareness Week
(March 8-14)
Focus on nutrition and rest — encourage balanced meals and better sleep habits.
APR
Alternatives:
Right On the Money
Work of Art
Financial Literacy Month
Stress Awareness Month
Earth Day (April 22)
Use spring energy to promote movement and mindfulness while adding a financial well-being tie-in.
MAY
Alternatives:
Chirpy
Good Nurtured
National Physical Fitness and Sports Month
Global Big Day (May 9)
Celebrate mental and physical health with challenges that get people outdoors.
JUN
Alternatives:
Coast to Coast
Star Trak
Great Outdoors Month
Make the most of warm weather with outside activities that prompt social connection.
JUL
Alternatives:
Good Nurtured
Summertime
Space Exploration Day (July 20)
International Self-Care Day (July 24)
National Park and Recreation Month
Blend self-care with learning and outdoor fun to inspire curiosity and balance.
AUG
Alternatives:
Colorful Choices
Feel Like a Million
Summer Sun Safety Month
Celebrate wellness in all forms — from sun protection to full-body activities.
SEP
Alternatives:
Right On the Money
Worldwide Wellness
National Fruits & Veggies Month
National Family Health & Fitness Day (September 26)
Tie in harvest-season produce with nutrition and family wellness activities.
OCT
World Walking Day (October 4)
Walk & Roll to School Day
(October 7)
Learn why Walktober is the only choice for October.
Walking + fall colors = unbeatable participation.
NOV
Alternatives:
Good Nurtured
Nourish
Generate mindful habits and healthy eating before the holiday rush.
DEC
Alternatives:
Health for the Holidays
Right On the Money
National Influenza Vaccination Week (December 6-12)
Uplift participants and increase energy during shorter days with consistent activity.
January
Alternatives:
Right On the Money
Snow Wonder
Observances:
New Year’s Resolutions Week
(January 1-7)
Financial Wellness Month
Planning Tip:
Kick off the year with a fresh start — combine movement with financial wellness tips to tap into resolution energy.
February
Alternatives:
10K-A-Day
Colorful Choices
Observances:
Random Acts of Kindness Week (February 14-20)
American Heart Month
National Cancer Prevention Month
Planning Tip:
Pair health goals with acts of kindness for a well-rounded wellness boost.
March
Alternatives:
Colorful Choices
Good Nurtured
Observances:
National Nutrition Month
World Compliment Day (March 1)
National Sleep Awareness Week (March 8-14)
Planning Tip:
Focus on nutrition and rest — encourage balanced meals and better sleep habits.
April
Alternatives:
Right On the Money
Work of Art
Observances:
Financial Literacy Month
Stress Awareness Month
Earth Day (April 22)
Planning Tip:
Use spring energy to promote movement and mindfulness while adding a financial well-being tie-in.
May
Alternatives:
Chirpy
Good Nurtured
Observances:
National Physical Fitness and Sports Month
Global Big Day (May 9)
Mental Health Awareness Month
Planning Tip:
Celebrate mental and physical health with challenges that get people outdoors.
June
Alternatives:
Coast to Coast
Star Trak
Observances:
Men’s Health Month
Great Outdoors Month
Planning Tip:
Make the most of warm weather with outside activities that prompt social connection.
July
Alternatives:
Good Nurtured
Summertime
Observances:
Space Exploration Day (July 20)
International Self-Care Day (July 24)
National Park and Recreation Month
Planning Tip:
Blend self-care with learning and outdoor fun to inspire curiosity and balance.
August
Alternatives:
Colorful Choices
Feel Like a Million
Observances:
National Wellness Month
Summer Sun Safety Month
Planning Tip:
Celebrate wellness in all forms — from sun protection to full-body activities.
September
Alternatives:
Right On the Money
Worldwide Wellness
Observances:
National Fruits & Veggies Month
National Family Health & Fitness Day (September 26)
National College Savings Month
Healthy Aging Month
Planning Tip:
Tie in harvest-season produce with nutrition and family wellness activities.
October
Observances:
World Walking Day (October 4)
Walk & Roll to School Day (October 7)
Breast Cancer Awareness Month
Planning Tip:
Learn why Walktober is the only choice for October. Walking + fall colors = unbeatable participation.
November
Alternatives:
Good Nurtured
Nourish
Observances:
Diabetes Awareness Month
World Kindness Day (November 13)
Planning Tip:
Generate mindful habits and healthy eating before the holiday rush.
December
Alternatives:
Health for the Holidays
Right On the Money
Observances:
National Influenza Vaccination Week (December 6-12)
Seasonal Affective Disorder (SAD) Awareness Month
Planning Tip:
Uplift participants and increase energy during shorter days with consistent activity.
Questions
What is the best way to plan workplace wellness challenges for a full year?
Build an annual wellness challenge calendar that matches your organization’s culture and health priorities. Start with your top goals, then select challenges aligned with seasonal observances. A structured plan keeps participation consistent.
How can I keep employees engaged in wellness challenges all year?
Keep it fresh and inclusive — offer different challenge types, tie activities to awareness months, and recognize progress often. Rewards, shout-outs, and team-based goals add excitement.
Read more: From Challenge to Change: 15 Ways to Build on Successful Walking Challenges.
What types of wellness challenges work best in the workplace?
Choose challenges that are simple to join, adaptable to all abilities, and encourage healthy habits in every part of life.
Read more: 10 Must-Do Workplace Wellness Challenges to Increase Physical Activity and Reduce Stress.
How far in advance should I schedule employee wellness activities?
Plan at least 3-6 months ahead to allow for promotion, leadership buy-in, and alignment with other organization events. An annual calendar helps you stay organized and adaptable.
Can small organizations benefit from a wellness challenge calendar?
Yes! Expect your well-planned program to increase enthusiasm, camaraderie, and well-being results —whether you have 20 employees or 2000.
Where can I find ready-to-use wellness challenges for my team?
Explore HES’s library of turnkey wellness challenges — fully hosted, easy to launch, and designed to support all facets of well-being. Pair them with this calendar for a consistent, high-impact program.