Everyone starts somewhere.

Helmets: legally required in Ontario for riders under 18, and strongly recommended for everyone else. A basic helmet from any Canadian Tire costs about $30 and does the job. You don't need anything carbon-fibre or aerodynamic. You just need something on your head that's properly fitted.

Lights: if there's any chance you'll be out near dusk — and Toronto summer dusk sneaks up on you — a front white light and a rear red light are legally required on roads and just good sense on trails. Cheap clip-on USB lights from Amazon or MEC work perfectly. You can get a set for under $20.

The passing rule: when you're overtaking a pedestrian or a slower cyclist, call out "passing on your left" before you do it. This is the universal trail etiquette and it prevents a lot of startled people and awkward swerves. Say it clearly, not aggressively. A friendly heads-up is all it takes.

Stay to the right on shared paths except when passing. Think of it like driving — keep right, pass left. Simple.

Slow down at blind corners and underpasses — especially the ones on the Don Valley Trail. Some of those underpasses are narrow and you can't see who's coming from the other side. Call out before entering. It takes two seconds and could save you a collision.

Pedestrians always have right of way on multi-use trails. Slow down around dogs and kids especially — they're unpredictable and that's nobody's fault. A gentle bell ring or a "heads up" from a distance gives everyone time to react.

On road sections: ride with traffic, not against it. Use hand signals for turns — left arm out for left, right arm out for right. Make eye contact with drivers before crossing intersections. If you can't tell if they've seen you, assume they haven't.

Don't ride with headphones in both ears. I know. But one ear out so you can hear what's happening around you — other cyclists passing, dogs, someone calling out — makes a real difference. Bone conduction headphones are a great compromise if music is non-negotiable for you.

Lock your bike whenever you leave it, even for five minutes. A basic U-lock is enough for most Toronto trail stops. Cable locks can be cut in seconds — a U-lock at least buys you real security. Lock through the frame and rear wheel if you can.

Toronto's trails are genuinely safe, well-maintained, and full of friendly people. These rules exist to keep everyone comfortable, not to scare you off. I've been riding here for years and the community on the trails is one of the best things about it.

You do not need cycling clothes. I want to be clear about this. Wear whatever you'd wear on a comfortable walk. Jeans are fine. Shorts are fine. A t-shirt is fine. The only thing I'd avoid is very loose trousers that could catch in the chain — roll up the right pant leg or use a cheap pant clip if you're worried. That's it.

Layers in shoulder seasons. Toronto mornings in April and October can be 8°C when you set off and 18°C an hour in. A light zip-up you can tie around your waist is the move. I've been caught without one more times than I'd like to admit.

Shoes: anything with a reasonably stiff sole works. Running shoes are fine. Sneakers are fine. Flip flops are not — your feet will slip off the pedals and you'll hate every second of it. That's the only hard rule here.

What to bring in a small bag or backpack:

Water — more than you think you'll need. At least 500 ml for every 10 km. Dehydration sneaks up on you, especially in summer when you're near the lake and there's a breeze making you feel cooler than you are.

A snack. Bananas, a granola bar, whatever you like. About 30 minutes in, you'll be glad you have it. Your body burns through fuel faster than you'd expect on a bike.

Your phone, fully charged. For maps, for photos, and for calling someone if you need to. Keep it in a zip pocket or a bag — not your back jeans pocket where it'll bounce out on a bumpy section.

$20 cash. For the café at the end, for the unexpected ice cream truck, or for the TTC if you decide you're done riding and want to bus home. Cash is freedom.

A basic bike lock. Even if you're planning to stay on the bike the whole time, you might spot a café or a bench or a view that makes you want to stop. Having a lock means you can.

Sunscreen if it's summer. The waterfront trails have almost no shade and the lake reflects light right back at you. You'll burn faster than you think.

What you don't need to bring: a repair kit on your very first ride. Keep it simple. Get comfortable with riding first. If something goes wrong, there are options (see the next section).

The best kit is whatever gets you out the door. Don't let gear be the reason you don't go. I rode my first trail in jeans and old running shoes and had the time of my life.

Flat tire — the most common thing that goes wrong, and honestly not a big deal. If it happens, don't panic. Find a safe spot off the path. If you don't have a repair kit (and you probably won't on your first ride — that's fine), Bike Share Toronto is your friend. Dock your bike at the nearest station and grab a Bike Share bike to get home. Most Toronto trails are within a few hundred metres of a Bike Share dock. Worst case, you walk for a bit. It's okay.

Chain falls off: this looks scarier than it is. Stop, flip the bike upside down (rest it on the handlebars and seat) or find a wall to lean it against. Then manually lift the chain back onto the smallest front gear ring. It takes about 30 seconds once you've done it once. Your hands will get greasy — bring a small cloth or paper towel, or just accept it. Greasy hands are a badge of honour.

You took a wrong turn: don't stress. Google Maps has a cycling mode that works well across most of Toronto's trail system. If you're deep in the ravines and don't have signal, keep following the trail in one direction — they all connect to streets eventually. You won't get permanently lost in Toronto. The city is always closer than it feels from inside a ravine.

You're exhausted and far from home: you have more options than you think. Bike Share docks exist throughout the city if you need to swap to a fresh bike. TTC buses have bike racks on the front — they're free to use, and loading your bike takes about ten seconds. The GO Train takes bikes at no extra charge. You always have a way back.

You fell: take a breath. Check yourself before you check the bike. Most trail falls are low-speed and result in scrapes at worst. Clean any wounds when you get home — soap and water, nothing fancy. If something feels wrong — head, wrist, collarbone are the common ones — get it checked at a clinic. Don't ride on a sore wrist hoping it's fine.

Something going wrong on a ride is a rite of passage. It happens to everyone and it's almost always less bad than it feels in the moment. The stories you'll tell later are always the ones where something went sideways.