7 Best Apps for Running Challenges With Friends (2026)
The awkward 2026 fact first: the app everyone assumes is the answer — Strava — put group challenges behind its subscription this year. Free accounts can no longer create or join one.
So "best" now splits into two honest categories: free social tracking, where the challenge costs nothing and the prize is bragging rights, and real-money stakes, where the group puts cash in a pot and the leaderboard actually pays. Here's what's genuinely alive in each.
Bragging-rights challenges: six apps that still work
These are the apps where a challenge costs nothing (or close to it) and the prize is the group chat. All six are verifiably alive in 2026 — which is not nothing: two apps that used to make every list like this one, Rival and FitNow's Challenges, haven't shipped an update in over a year, so they're out.
1 · Strava
Still the social layer of running — segments, clubs, the feed. But know what you're buying: group challenges with friends now require a subscription ($11.99/month or $79.99/year) to create or join, per Strava's own support pages. Subscribers can invite up to 199 followers per challenge. The free tier still tracks and shares runs fine.
2 · Nike Run Club
The best fully free answer. Create a distance challenge, set the dates, share it with friends — no paywall anywhere, plus genuinely good guided runs. The trade-off: it's Nike's closed world. No Strava sync, so your challenge lives where your friends' Nike accounts are.
3 · Stridekick
Challenge-first by design: leaderboard, streak, target and virtual-race modes against friends. Free covers public challenges up to 10 people and 7 days; private or longer challenges need a Pro plan (from $12.99/month) — but only the organizer pays, invitees join free. Syncs Fitbit, Apple Watch, Garmin, Polar and phones; notably, not Strava.
4 · Miles With Friends
The scrappy free option: private group challenges with a share link, leaderboards, and some 70 activity types converted into mile-equivalents so the cyclist in your group can't sandbag. One honest caveat — it's a web app. The native iOS/Android apps are still "coming soon," and device sync is Fitbit-only.
5 · RaceMe
The only one here that does live racing: you and a friend start together and watch the gap in real time, with in-app chat for trash talk. Free with a Pro tier at $4.99/month or $19.99/year. The catch is platform: iPhone and Apple Watch only, so every friend needs an iPhone.
6 · Squadrats
The wildcard. Not a challenge app in the invite-your-friends sense — it carves the world into map tiles and you "collect" every tile you run through, straight from your Strava uploads. Free with a paid tier for regional leaderboards. In practice, a friend group racing to the biggest square is one of the most addictive month-long competitions running has.
When the leaderboard should actually pay: RunMatch
Disclosure up front: this is our app. It's on the list because it's the category — running challenges with friends is literally the product — but you should read this entry knowing who wrote it.
7 · RunMatch
OursEveryone puts a buy-in into a pot, everyone runs, the winner gets paid. Three formats — Race (first to the distance), Most Miles (7 days), Streak (daily minimum, last one standing).
- 1Every run is GPS-verified through Strava — no self-reported miles, no arguments.
- 2Pots are automatic: buy-ins lock at the start, the winner is paid out at the end. No Venmo collection.
- 3We take nothing from the pot — a 3% fee applies only at withdrawal, on Stripe rails. 18+, iOS.
Why money changes the challenge
Free challenges die quietly in week two — someone stops logging and nobody says anything. A pot changes the physics: quitting now costs something, and the person in fourth place on Thursday night suddenly finds a reason to run.
If you're weighing the whole stakes category, we compared StepBet, DietBet, HealthyWage and the rest — house cuts included — in apps like StepBet (but better), and the honest earnings ceiling for every "get paid to run" model in what the apps actually pay. Want the exact take-home for your group's pot? The payout calculator does the math.
All seven, one table
| App | Challenges with friends | Price reality |
|---|---|---|
| Strava | Group challenges, up to 199 invitees — subscribers only (to create and to join). | Free tracking; $11.99/mo or $79.99/yr for challenges. |
| Nike Run Club | Create and share distance challenges with friends. | Free, full stop. |
| Stridekick | Leaderboard, streak, target and virtual-race modes. | Free ≤10 people / 7 days; organizer Pro from $12.99/mo, invitees free. |
| Miles With Friends | Private group challenges, ~70 activities, share link. | Free — but web app only, Fitbit sync only. |
| RaceMe | Live head-to-head races with chat. | Free; Pro $4.99/mo or $19.99/yr. iOS/Watch only. |
| Squadrats | Map-tile collecting and leaderboards via Strava. | Free; paid tier for regional rankings. |
| RunMatch (ours) | Race, Most Miles, or Streak — for a real pot, Strava-verified. | Free to download; you set the stakes. No pot cut, 3% at withdrawal. 18+, iOS. |
Which app should your group pick?
Match it to what your group actually needs:
- Everyone's already on Strava and someone pays for it → Strava group challenges. Cleanest if the subscription doesn't bother you.
- Zero budget, mixed phones → Nike Run Club, or Miles With Friends if your group mixes runners with cyclists and walkers.
- Step-style office challenge energy → Stridekick — one organizer pays, everyone else joins free.
- You want to literally race, live → RaceMe (all-iPhone groups only).
- A month-long territory war → Squadrats.
- The group chat needs consequences → RunMatch. Real pot, Strava-verified miles, automatic payouts — and yes, it's ours; the mechanics above are the pitch.
Common questions
Make the group chat put up or shut up.
Run 1 mile, get $10 — then race your friends for a real pot, GPS-verified through Strava.
Get RunMatch on iOSOne $10 first-mile reward per new account · 18+ · Terms apply