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Challenging Hikes Toronto

Your next hiking adventure starts here

Hike the Don!

Hike the Don!

Sat, Oct 3, 4:30 PM
From Vibe & Wander
4.8

Time to trade the city streets for some woods, ravines, hills and good company! We’ll head into Crothers Woods and explore the trails through the Don Valley. Expect a mix of forest paths, gentle climbs and uneven terrain. Meetup Fee - $2 (E transfer to mech.mandeep@gmail.com or vibhuchaudhary@yahoo.com) πŸ₯Ύ Moderate | ~6–7 km ⏱️ 2–3 hours πŸ”„ Loop β€” we’ll finish where we started We’ll hike at a moderate pace, keep it social and enjoy the trail. A little mud, roots and hills are all part of the adventure! πŸ‘Ÿ Bring: Comfortable hiking shoes, water and a snack. Dress for the weather. πŸš— Parking is available near the trailhead, and the area is also accessible by TTC.

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9 attendees
Seaton Trail

Seaton Trail

Fri, Oct 16, 9:30 PM
From Move With Intention
4.9

**I’m organizing a fall hike at Seaton Trail in Pickering October 16, at 5 30 p.m.** **We’ll aim for an 8–10 km hike, taking approximately 3–4 hours at a moderate pace, with breaks to enjoy the fall colours and take pictures.** **It should be a lovely opportunity to enjoy nature, get some exercise and meet new people.** **Bring comfortable hiking shoes, water and snacks. Let me know if you’d like to join!**

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6 attendees

Midweek morning hike - Earl Bales

Tue, Nov 3, 3:00 PM
From Trail Hike - Richmond Hill
4.9
9 attendees
Utah Hiking Trip

Utah Hiking Trip

Sat, Oct 10, 11:00 PM
From Utah Hiking

Hike in monument valley and visit archesnational park for a moderate hike

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1 attendee

Early Morning Hike at the Lake!!! 🌞Scarborough lakeshore. 🌊 🦒

Sun, Oct 11, 11:00 AM
From 2&4hr -Advanced Hikes TORONTO
4.9
5 attendees

Boyd Conservation Area - Intermediate Hike.

Sun, Oct 4, 1:00 PM
From 2&4hr -Advanced Hikes TORONTO
4.9
2 attendees
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Frequently asked questions

Meetup connects people through shared interests. Whether you're into hiking, tech, or a particular hobby, it helps you find events and groups to join.

Use Meetup to search for hiking events in Toronto. You can filter by the activity type to find challenging hikes that match your experience level and interest.

Yes, there are several hiking groups in Toronto. These groups organize regular events and hikes, including challenging ones, allowing you to meet other outdoor enthusiasts.

Absolutely! Meetup lets you join as many groups as you like. It's a great way to increase your chances of finding hikes that meet your interests and schedule.

Some hikes may require special gear based on their difficulty. Always check the event details on Meetup, which often include gear recommendations from the organizers.

Many Meetup events are free, but some may have a fee. It varies by event and organizer, so check the event's description for specific details.

Once you find a hike you'd like to join, click on the event and use the RSVP button to indicate your attendance. It's simple and updates the organizer immediately.

Meetup covers a variety of activities, from relaxed to challenging. Join groups and choose events that fit your interest; challenging hikes are just one option.

Yes, if you're interested in leading a hike, you can organize an event on Meetup. You'll need to start your own group or join one as an organizer.

While Meetup brings together people with common interests, the level of expertise varies. Engaging actively helps meet people aligned with your hiking skill level.

Meetup encourages group interaction which can be safer, especially for challenging hikes. Always follow event guidelines and connect with others at the event.

Meetup facilitates connections but can't control weather or trail conditions. Always check local reports and prepare accordingly.

Availability of hiking events may vary by season. Toronto has active outdoor communities, but check regularly to see upcoming hikes.

Most hikes are in-person, and group meetings are scheduled to explore trails together. Always check event details, as some activities might also be virtual talks or preparations.

Absolutely. While this page focuses on challenging hikes, Meetup caters to all skill levels. Look for beginner-friendly groups and grow your skills with others.