Toronto is a city of six million people, and somehow, finding someone to go hiking with is genuinely hard.
Most people I talk to who want to get outside face the exact same problem: they moved here for work, or their friends aren’t into it, or life got busy and their outdoor crew evaporated. The desire is there. The company isn’t.
This post is for those people.
There’s a particular kind of loneliness in wanting to do something outdoors and not having people to do it with.
You can hike alone, and plenty of people do. But there’s something fundamentally different about spending a long day in the woods with good company. You stop more. You notice more. You stay longer.
The city doesn’t make it easy to find those people either. Most outdoor groups in Toronto are either volunteer-run with an older demographic, or they’re massive Meetup groups where you show up as a stranger and leave as a stranger.
The options exist. They’re just not all created equal.
Meetup.com
There are several active outdoor groups in Toronto on Meetup. The Hiking Network, GTA Hiking & Stuff, and a handful of others run regular outings. The quality varies. Some are well-organised with experienced leaders; others are more casual.
Good for: getting outside quickly, low commitment, free or cheap. Worth knowing: group sizes can be large, and the community stickiness is low. You might meet someone great. You might not.
Toronto Outdoor Club
100% volunteer-run, been around for decades. Extremely busy calendar. The reputation is solid and events are well-run.
Worth knowing: the average member skews older than the 25 to 38 range that most of the people reading this are in. If that doesn't matter to you, it's a good option.
Facebook Groups and Reddit
Toronto has active hiking communities on Reddit (r/torontohiking) and several Facebook groups. Good for real-time beta on trail conditions and spontaneous plans.
Less structured than a club, but if you're looking to link up with someone for a specific hike, it works.
Wilderness Union
This is what we built.
We vet every member. Not in an exclusionary way - in a "we want everyone in the group to have a genuinely good time and feel safe" way. The age range is 18 to 45. The majority of our members are in the 25 to 38 bracket, working professionals, a mix of people who grew up here and people who moved here from somewhere else.
Every trip is guided by someone who knows the route and the group. We handle the transport, the gear, and the logistics. You show up.
Most people who join do so specifically because they don't have outdoor people in their lives. That's not unusual here. It's basically the baseline.
Vetting doesn’t mean we’re turning people away based on experience level. You can be a total beginner, we love beginners!
It means everyone in the group is in a similar life stage, shows up with the right attitude, and treats the experience - and the other people in it - with respect. The community quality is something we actively protect, because once you let it slip, the thing people actually come for disappears.
If someone isn’t right for the group, we let them know honestly. That’s not a rejection, it’s us doing our job and protecting the experience for everyone on the trip.
You book a trip and get a confirmation. A few days before, you get the full trip plan - what to bring, where to meet, what the day looks like.
On the day, you show up to a pickup point close to Keele Station. You get on a coach with anywhere from eight to twenty-something people. Nobody knows each other at the start. That’s completely normal and nobody expects you to.
The guide handles the day. You hike, you take breaks, you eat lunch somewhere scenic. By the afternoon, you know at least a few people by name. By the end of the trip, you’ve spent six or seven hours with people who chose to spend their Saturday the same way you did.
That’s a good start.
Most people come not knowing a single person in the group and leave with a friend group they didn’t see coming.
It sounds like a line, but it’s the thing we hear back more than anything else. The outdoors strips away a lot of the social armour that city life puts up. You’re not networking. You’re just hiking.
The friendships that form on these trips tend to stick, because they’re based on something real.
There’s no membership requirement to book your first trip with Wilderness Union. Sign up, pick a trip that looks interesting, and show up.
If you want access to the full trip calendar, discounted pricing, and the advanced and multi-day expeditions, an Explorer membership is $180 for the first year (then $90 on renewal). There’s a one-month free trial.
But you don’t need any of that to get started. The easiest version of this is just booking a trip.
Check out what’s coming up and find something that works for you. We hope to see you out there.
Can I go hiking in Toronto alone as a complete beginner? Yes. Solo hiking is fine on well-marked trails close to the city. If you're going somewhere more remote, tell someone your plan and expected return time. Joining a guided group is the easiest way to start safely if you're new to hiking.
What's the best way to meet people through outdoor activities in Toronto? The most reliable options are Wilderness Union (vetted community, guided trips), the Toronto Outdoor Club (volunteer-run, well-organised), and Meetup groups like the Hiking Network. The quality of connection varies by format - smaller, guided groups tend to produce stronger friendships than large open groups.
Do you need experience to join a hiking group in Toronto? No. Most groups, including Wilderness Union, actively welcome beginners. The main thing to get right is being honest about your fitness level when you book, so you end up on a trip that's right for you.
Is it weird to show up to a hiking group not knowing anyone? Not at all. It's the norm, honestly. Most people who join outdoor groups in Toronto do so specifically because they want to meet people. You won't be the only one.
What should I bring on a hiking trip if I'm just starting out? Comfortable hiking shoes or trail runners, layers, 2 litres of water, snacks, sunscreen, and a hat. If you're coming on a Wilderness Union trip, we'll send you a full packing list before the day.
