Find Your Path Through Holiday Grief
The holidays can feel impossible when you’re grieving. This challenge gives you a gentle way to move through the season when everything feels heavier than usual.
Join for $29 — or get it free inside the 100 Walks Club ($9/month). The challenge begins December 16, and you’ll receive your resources a few days early so you never feel rushed.
What is the Healing Walks Holiday Challenge?
The holidays have a way of magnifying loss.
A song in a store.
An empty chair at the table.
A tradition you’re not sure how to face this year.
When you’re grieving, the world feels festive — and you just feel cracked open. You might be exhausted from trying to act “okay,” or avoiding celebrations because it hurts too much.
This challenge offers a gentler way through. Walking is one of the simplest ways to steady yourself when everything else feels overwhelming, and this challenge gives you a quiet rhythm to lean on.
Through slow daily walks and mindful prompts, you’ll move through the season with gentle support — finding small pockets of peace without pressure or forced positivity.
How The Challenge Works
🗓 December 16 – December 31
🚶♀️ One walk a day — anywhere, anytime
📝 Daily grief-informed prompts in your inbox
🎁 Unlock a Winter Walks bonus gift when you finish
Each piece is designed to meet you where you are, especially on the hard days.
❄️ You can join the standalone challenge for $29, or get it free as a member of the 100 Walks Club.
They say it’s the most wonderful time of the year. No one tells you what to do when it becomes the hardest. You don’t have to walk through it alone.
Who Is This Challenge For?
This challenge is for you if…
The holidays feel different this year — heavier, quieter — and you don’t have it in you to pretend otherwise.
You want a gentle way to get through the season without shutting down or forcing yourself to be “festive.”
You’d welcome having a calm place to land — somewhere you don’t have to explain your grief or act like you’re okay.
If you’re carrying grief into this season — whether your loss is recent or something you’ve lived with for years — this challenge will hold space for you.
What You’ll Receive
Daily Prompts Delivered to Your Inbox
Each day, you’ll receive a gentle email guide for your walk — created specifically for holiday grief. These prompts help you move through memories, guilt, longing, and the tender contradictions December brings.
Holiday Grief & Walking Reflection Journal
A dual-purpose printable journal to hold everything that rises during these 16 days — your memories, your pain, your hopes, your reflections. Each page invites you to honor your experience exactly as it is.
Printable Companion Cards
Beautiful walking prompts you can tuck into your pocket or journal — perfect for screen-free walks or quiet moments when you just need a little guidance.
And to gently support you even more through the season…
You’ll also receive a special bonus — plus optional community support if you choose the Club.
🎁 Winter Walks Bonus Collection
Complete all 16 walks and unlock a bonus set of 25 winter-themed walking prompts — created to support you through the quieter winter months with rest, reflection, and gentle brightness — a soft companion for the weeks that often feel the loneliest.
🎴 Optional Support Inside the Club
If you join the 100 Walks Club instead of the standalone challenge, you’ll be welcomed into a cozy, uplifting space on Skool — a little sanctuary filled with kind people who are also walking their way through the season.
Inside, you’ll find gentle motivation, quiet companionship, and a sense of being part of something bigger — without any pressure to share or open up. You can simply show up, read along, and let the warmth of the community walk beside you.
Sometimes just knowing you’re not walking alone makes all the difference.
Challenge FAQs
Have questions? Here’s what most people ask before joining…
How long do my walks need to be?
You only need about 10 minutes for each walk — just enough to step outside, breathe, and move a little. If you’d like to stay out longer, you’re always welcome to. This challenge meets you where you are. Even the smallest amount of movement can create a shift when you’re grieving.
What do I get when I finish?
When you complete all 16 walks, you’ll unlock the Winter Walks Bonus Collection — 25 additional walking prompts to support you through the rest of the season with calm, reflection, and gentle brightness. It’s a way to keep caring for yourself after the holidays quiet down.
Can I gift this to someone else?
Yes. Just email hello@100walks.com and we’ll help you set up a gift for someone who could use a little extra support this season. It’s a simple, heartfelt gift that truly supports someone through a hard season.
How long do I have access to the challenge?
You’ll have access through the entire holiday season — until January 31st — so you can move through the materials at your own pace. Many people save the prompts and return to them whenever they need a moment of grounding.
You’ll have plenty of time and space to move through the materials gently.
Join the 2025 Healing Walks Holiday Challenge
OPTION 1
Just want the challenge?
OPTION 2
Get it free when you join the 100 Walks Club.
When you click ‘join now’, you’ll be taken to our private Skool group to complete your purchase. Cancel anytime.
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