TRAILSY
Ride the pack.
Split the pot.
Pick a pack of Bend trails. Ride every one before the window closes. Everyone who finishes splits the pool — no stopwatch, no draw, no cut for us.
Why it's fun
A scavenger hunt, on your favourite trails, with money on it
You already ride. Trailsy gives the ride a list, a deadline, and a pot — and the only person standing between you and a payout is you.
Tick off every trail in the pack
A pack is a hit list: six trails, twelve, whatever the pack says. Ride one end to end and it goes green on your map and stays green. Finishing the list is the whole game.
Win the pool
Every buy-in goes in the pot. Finish, and you split it with the other finishers. Fewer finishers, bigger share.
Meet people out there
Post a group ride, see who's in, and clear three trails together instead of alone.
A map that fills in forever
Every verified ride colours in another line of Bend. Packs end; your map doesn't.
How it works
Four steps, start to payout
Trailsy is an iPhone app, and it never records anything. It reads the rides you already put on Strava and decides whether they cover the trails in your pack.
Connect Strava
Sign in with Apple, then link Strava once. We read your rides so we can score them. We never post to your Strava, and never show another rider your Strava data.
Join a pack
Each pack lists its trails, its window, its buy-in, the processing fee and the total charge before you confirm. Free packs cost nothing and pay nothing.
Ride the trails
Ride each required trail end to end in a single ride, inside the window. Either direction counts unless the trail is one-way. Nothing is timed.
Split the pool
When the window closes, the pool — every buy-in, including from riders who did not finish — is divided equally among the finishers and paid out through Stripe.
A contest of skill, not a game of chance
Nothing in a pack is random. Whether you finish depends only on your own riding: you ride every required trail inside the window, or you do not. Finishers are not selected, they qualify, and there is no cap on how many riders can win. Trailsy is not a sportsbook, a lottery or a fantasy contest, and riders never wager against each other or against the house.
Open now
Join a pack
These are the packs taking riders right now, straight from the app. Grab one in Trailsy.
Loading the shelf…
One second — we're asking the app which packs are open.
Pools grow as riders join, so the number on a card is what is in the pot right now, not a promise of what you'd win. The app shows every pack's trails, window and exact charge before you enter.
Pricing
What you pay, to the cent
No subscription, no membership. One charge, when you enter a paid pack, shown in full before you confirm. All prices in US dollars.
Example: a $20 pack
Illustration only. Each pack sets its own buy-in.
- One charge per pack you enter. Buy-in plus processing fee, taken at enrolment. No recurring billing, ever.
- The pool is sacred. It is made of buy-ins only, and 100% of it is paid to finishers or returned to riders. Leftover cents go to riders, not to Trailsy.
- Nothing is taken from your winnings. No payout fee, no withdrawal fee. Payouts go through Stripe to the payout account you set up in the app.
- Free packs are free. No buy-in, no processing fee, no prize money — just the map and the finish.
Who can ride
Before you enter
Trailsy is deliberately small at launch: one town, one set of rules we can actually enforce.
18 or older
Everyone using Trailsy must be at least 18. Stripe verifies identity before any payout is released.
Oregon, for paid packs
You must be an Oregon resident and physically in Oregon when you enter a paid pack. Free packs are open more widely.
An iPhone and a Strava account
Trailsy is an iOS app. Rides must reach Strava on the account you connected — a ride we never receive cannot be counted.
One account per person
Entering through more than one account means disqualification and forfeiture of the buy-in to the pool.
Real rides only
Fabricated or edited GPS files, files shared between accounts, and rides recorded from a vehicle are grounds for removal and a ban.
E-bikes welcome
Packs are not timed, so e-bikes are allowed unless a pack says otherwise. Record e-bike rides as e-bike rides.
Refunds & cancellations
When money comes back
These are the rules shown on a pack before you enter, and they do not change once a pack is running.
| Situation | What happens |
|---|---|
| You withdraw before the window opens | Your buy-in is refunded in full to your original payment method. The processing fee is not refunded. |
| You withdraw after the window opens | No refund. Your buy-in stays in the pool for the riders who finish. |
| Trailsy cancels the pack | Every buy-in and every processing fee is refunded in full, including if we cancel because too few riders joined or a trail became unridable. |
| Nobody finishes the pack | Each enrolled rider is refunded the percentage of their buy-in shown on that pack's page before entry — 90% unless the pack says otherwise. |
| Injury, our mistake, or an entry made by accident | Reviewed case by case. Email us before the pack settles wherever possible. Any refund we grant comes from Trailsy's own funds, never from the pool. |
| You think a ride was scored wrongly | Email us with the activity link before the pack settles, and within 7 days of settlement at the latest. An error on our side is corrected. |
Refunds of card charges go back to the original payment method. Pool money — winnings and refunded buy-ins after settlement — is paid through Stripe to your payout account, normally within a few business days. Questions about a specific charge go to [email protected]; please email us before disputing a charge with your bank, so we can fix it faster than a chargeback can.
Questions
The things people ask first
How is a ride verified?
We compare the GPS track your device recorded, as uploaded to Strava, against our own map of the trail, built from OpenStreetMap data. Normal GPS wobble under trees is expected and allowed. A track that only crosses the trail, leaves it for long stretches, or was recorded on the road beside it will not count.
What if only one rider finishes?
That rider receives the whole pool. There is no minimum or maximum number of finishers — the fewer riders finish, the larger each share.
How does Trailsy make money?
Only from the processing fee charged at entry — $0.50 plus 4% of the buy-in by default, shown to the cent before you pay. We take nothing from the pool and charge nothing to pay you out.
When do I get paid?
Packs settle after the window closes plus a short grace period for late Strava uploads. Winnings are sent through Stripe to your payout account, normally within a few business days of settlement. You need to finish Stripe's payout setup, including its identity check, before we can send money.
Is this gambling?
No. A pack has no random element and no house edge. You are paid for completing a physical task you control, every finisher is paid, and Trailsy's revenue is a disclosed fee charged on top of the buy-in rather than a cut of the money at stake.
What happens if a trail closes mid-pack?
If a land manager closes a trail, or fire, snow or damage makes it unridable, we may make that trail optional for everyone, substitute a comparable trail, extend the window, or cancel the pack and refund in full. Enrolled riders are notified in the app. Never ride a closed trail for a pack.
Is there a snow version?
The app already understands ski and snowboard packs, and Gnar has the goggles to prove it — but every pack open today is a mountain bike pack on Bend singletrack. Mt Bachelor packs are what we are building toward this winter. Join the beta and you will hear when the first one opens.
Will I actually see Gnar out there?
No. Gnar is our mascot, not a trail hazard. If you do see a sasquatch in the Deschutes National Forest, that is between you and the sasquatch, and Trailsy cannot verify it from a GPS track.
Put something on the line.
Trailsy is in beta in Bend, Oregon, run by a small team who ride here. Support, refund requests, scoring disputes and press all go to the same inbox, and we read every message — expect a reply within two business days.
[email protected]