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Monthly Walking Challenges: A New Peak to Climb Every Month

S Strideora team · 4 min read

Three cartoon mountains getting taller, joined by a dotted gold trail: a small hill with a sprout, a middle mountain where four hikers climb with a gold flag, and a snowy peak topped with bunting and confetti as a rocket flies past.

There’s something about a fresh month. New page on the calendar, a little burst of “right, let’s do this”. Strideora’s monthly league challenges are built to bottle that feeling and share it with your whole walking group.

Our motto for it is simple: every month, a new peak to climb.

Why monthly?

A month is a lovely length for a challenge.

  • Long enough to build some momentum and see a habit take shape.
  • Short enough that the finish line always feels within reach.
  • Regular enough that if one month doesn’t go to plan, the next one is a clean slate.

Year-long goals can feel endless. Weekly ones can feel like a treadmill. A month sits nicely in the middle.

How Strideora’s monthly league works

In Strideora, everyone in your group has their own private daily step goal. The group score is the share of member-days where people hit their own goals. So it’s a team effort, not a contest between friends.

The monthly league gives that team effort a target. When the organiser starts the group, they choose its league level:

  • Relaxed: a gentle climb, perfect for new groups or anyone easing in.
  • Balanced: a steady, satisfying middle ground.
  • Ambitious: for a group that’s feeling bold and wants a proper summit.

Then, each month, the organiser sets the new challenge, and you walk the month together, cheering each other on in the activity feed, and finish with a monthly celebration of what you achieved as a team.

It’s the group against the mountain

This is the bit we love. In a lot of step challenges, the competition is between people. In Strideora, the competition is between your group and the peak.

That changes the mood completely. When your mate hits their goal, it helps you get up the mountain. When someone has a quiet week, the group rallies round instead of leaving them behind. Nobody’s step count is on show, and nobody’s at the bottom of a table.

Choosing the right level (organisers, this one’s for you)

The level is picked once, when you set up the group, so it’s worth a little thought. A few friendly tips:

  1. Think about everyone, not just the keenest walkers. The level should feel doable for the whole group, across busy months, dark evenings and holidays.
  2. New group? Start Relaxed. An early win feels brilliant and sets a positive tone.
  3. Ask before you start. A quick “how ambitious are we feeling?” in the group chat keeps everyone involved from day one.
  4. Then stick with it. You can change the level later, but it’s best not to. A steady level gives everyone a familiar target, and each new month brings its own fresh challenge anyway.

Make the month memorable

The challenge is the framework. What you do with it is up to you. Some ideas:

  • Give the month a theme. “Autumn colours month”, “explore a new park every weekend”, “walk to the shops instead of driving”.
  • Plan one walk together. Even if everyone walks separately day to day, a shared walk mid-month is a great boost.
  • Cheer generously. When the group gets a notification that someone’s hit their goal or kept a streak going, a cheer takes two seconds and can be the thing that gets them out of the door tomorrow.
  • Celebrate the finish. Strideora wraps up each month with a celebration for the group. Add your own: a café stop, a group photo, a slice of cake. You earned it.

What if we don’t make it?

Then you’ve still walked a month together, which is the whole point. Not every peak gets climbed first time. Have a laugh about it, cheer each other on, and go again when the next challenge arrives.

That’s the beauty of a monthly rhythm: there’s always a fresh start just around the corner.

Who monthly challenges are great for

  • Friends who want something to aim for without turning it into a competition.
  • Families looking for a shared project across generations.
  • Workplaces wanting a light-touch, inclusive way to get people moving together.
  • Clubs and community groups who like a reason to celebrate.

Your first peak is waiting

Strideora is coming soon to iPhone and Android. If you’d like your group to take on its first monthly challenge when it launches, join the waitlist on our coming soon page and we’ll email you as soon as it’s ready. Members join free, and organisers get their first month free.

See you at the summit.

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