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Challenging Hikes Toronto

Your next hiking adventure starts here

Midweek morning hike - Earl Bales

Tue, Nov 3, 3:00 PM
From Trail Hike - Richmond Hill
4.9
9 attendees
HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

Wed, Oct 14, 10:30 PM
From Ready, Set, Trail
5.0

Ready to sweat it out on the hills? Join us for a HIIT-style hill training hike This hike is part of the **HikeFit Series**, a collection of fitness-focused hikes designed to build strength, endurance, and overall hiking fitness. We’ll challenge you with steep climbs, rugged terrain, and a high-intensity workout. This isn’t a fast-paced hike, but it is **intense**. We’ll tackle multiple **very steep hills** in intervals, with plenty of chances to catch your breath, recover, or skip hills if needed. This hike is designed for intermediate hikers, but it’s **beginner-friendly** since you can skip as many hills as you need. It’s perfect for anyone looking to **get stronger, improve endurance, and boost their hiking fitness** at their own pace. **Weather-Dependent Notice:** The hike is a go, **(light)** rain or shine; However, if there's a risk of excessive mud making the hills too slippery, the hike will be canceled with around 24 hours’ notice. **Distance & Duration:** *Length of hike:* \~4 km *Event duration:* \~1.5 hours *Trail maps:* Random hill at Earl Bales park *Difficulty level:* L3 (Level 3/Moderate) * Terrain: L4 * Pace: L2 * Distance: L1 **What to Bring:** *Water:* +0.5 liters *Extras:* Hiking pole (Highly recommended) *Required Gear:* Hiking boots or Trail Runners with good grip, Headlamp, and by December [Microspikes](https://kahtoola.com/traction/microspikes-footwear-traction/?srsltid=AfmBOoqq-URDFRgNAISoLYH1l1cSLKeXOTSuU6EqUC6VupfLNZAGRg8P) **Costs:** *Member Event fee:* FREE EVENT **Travel Coordination:** No Travel Coordination for this Event, Meeting at Starting Point **Event Guidelines:** *Punctuality,* Please arrive on time so we can start promptly. We won't be able to wait for more than 5min past the start time *Pack out everything you bring* (including nut shells, fruit peels, etc.) to help keep our trails clean. ***RSVP:*** *Only those marked as “Going” and have confirmed travel details (if requested) are eligible to attend the event. If your **plans change** and you are no longer able to attend, please update your RSVP as soon as possible. No-shows without prior communication may result in removal from future events.* Weather Considerations **The hike is a go (light)** rain or shine, so please be prepared for the conditions. for example, If it’s expected to rain, waterproof gear (like a jacket or shoes) ***Pets:*** please check with the organizer for details before bringing your pet. Looking forward to seeing you on the trail

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3 attendees
🍂 Fall Walk: Rouge National Urban Park and  Picnic🌳

🍂 Fall Walk: Rouge National Urban Park and Picnic🌳

Sat, Oct 24, 1:45 PM
From No Such Thing As Bad Weather Walking & Hiking Group!
4.8

# 🍂🌳 Fall Walk: Rouge National Urban Park 🌳🍁 ### A Real Hike, Beautiful Fall Colours & a Picnic Together Want to get out of the city without actually leaving Toronto? **Rouge National Urban Park** is Canada's only urban national park — and one of the most popular hikes we do. Once you get onto the trail, it can be hard to believe you're still in Toronto. Forest paths, rolling hills, changing leaves, and quiet stretches of wilderness make this feel much more like a trip outside the city than a walk through it. And fall is one of the best times to experience it. This is **a real hike**, though. There are some hills and ups and downs, so it isn't the best choice if you're looking for an easy, flat walk. But if you're up for the challenge, there's something satisfying about reaching the end knowing you did it together. And then we'll have a picnic. 🧺 📱 Don't forget to join our **WhatsApp Group – [CLICK HERE](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** *** ## 🥾 What We'll Do We'll meet at **Don Mills Station** and take the 85C bus together toward Rouge National Urban Park. Once we arrive, we'll begin our hike through the park. Along the way we'll: * Hike through forest and open spaces 🌳 * Enjoy the fall colours 🍂 * Navigate the hills and changing terrain * Take in some beautiful views * Stop for a short break along the route * Finish at the Park's Welcome Centre * Have a **30–40 minute group picnic** afterward 🧺 The hike takes approximately **2½ hours**, plus a short break. Afterward, we'll take some time to relax, eat, and enjoy each other's company. *** ## 🍁 Fall Weather & Expectations This is a **moderately challenging hike**, not a casual stroll. There are hills, uneven sections, and some ups and downs, so good walking or hiking shoes are important. Please come prepared for typical fall weather and bring enough water for the hike. If you're comfortable walking for a couple of hours and handling some elevation changes, you'll be fine. If you're looking for something completely flat and easy, **this probably isn't the walk for you.** *** ## 🚌 Meetup Details ### 🚇 By TTC 📍 **Meetup Location:** Don Mills Station — on the platform for the **85C bus** 🫎 **Look for me in my Moose Hat!** ⏰ **Meetup Time:** **9:45 AM** 🚌 **Bus Leaves:** **10:06 AM sharp** I'll wait for the bus, but if you miss it, **you won't be able to join the group afterward.** **Early is on time. On time is late.** ### 🚗 By Car Parking is **not available at our TTC meeting point.** If you're driving, please park at the **Toronto Zoo** and walk to the **Park's Welcome Centre (the house)**. 🚗 **Car Meetup Time:** 11:00 AM We may be a few minutes late arriving, depending on the bus and traffic. *** ## 🧺 The Picnic After the hike, we'll have a **30–40 minute group picnic** at the end. Please bring something small to share — nothing too large or heavy. The goal is simply to have something to eat together after the hike. 🥪 Sandwiches 🍎 Fruit 🍪 Snacks 🥤 Drinks Whatever is easy to carry and share is perfect. *** ## 🧢 Meetup Details at a Glance 🥾 **Hike:** Approximately 2½ hours + short break 🧺 **Picnic:** 30–40 minutes 🏁 **End Point:** Park's Welcome Centre 💲 **Meetup Fee:** $5 cash or e-transfer 📧 **mathewmaclean@hotmail.com** *** ## 🎒 What to Bring 💧 Water 🥾 Good walking shoes or hiking shoes 🥪 A snack 🧺 Something small to share for the picnic 🧥 A fall jacket or layers *** ## 🌈 Who Is This For? This hike is great for: * People who enjoy a little challenge * Anyone who wants to explore Rouge National Urban Park * People who love fall colours 🍂 * Hikers looking for a social outing * Anyone comfortable walking hills and uneven terrain * People who want to meet others while getting outside This isn't the easiest walk we do. **But sometimes the harder walks are the ones you remember.** You're welcome to RSVP ahead of time or just show up on the day if you're unsure about your schedule. Sometimes things happen and events may need to be cancelled or changed, so please keep an eye on the event page for updates. 👤 **Organizer: Mathew** Questions? Post on the event wall or email **torontomoviesandoutings@hotmail.com** **Come for the hike.** **Stay for the picnic.** **Leave with a new connection — and maybe a new friend.** 🍂💛

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21 attendees
Cliffs & Fall Colours: A Bruce Peninsula Hike

Cliffs & Fall Colours: A Bruce Peninsula Hike

Sun, Oct 18, 11:00 AM
From Wilderness Union Toronto - Outdoor Adventure and Hiking Club
4.7

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/bruce-peninsula-26)** **The Bruce Peninsula does dramatic better than almost anywhere else in Ontario, and fall is when it really shows off.** We'll be out for most of the day, covering 8.5km of moderate hiking through some of the best autumn scenery in the province, with the changing leaves against the escarpment's limestone making for a proper contrast. We'll start in the forest before the trail opens onto the coastline, tracing the cliffs down to the Grotto. It's the most photographed spot on the peninsula for good reason: crystal clear water, a sea cave carved into the rock, and a natural window out to the bay. We'll take our time here, including a stop for lunch. From the Grotto we'll keep following the shoreline out to Stormhaven, crossing pebble beaches with open views across Georgian Bay the whole way. We'll turn around there and retrace the coastline back, catching all the same cliffs and colour from the other direction with the light shifted by then. **Two important things to note:** 1. **Self driving isn't possible for this trip. Parking passes at the trailhead sell out well in advance, so all members travel together on WU transport.** 2. **Bruce Peninsula National Park is stunning, but be aware that it is a long drive there and back. Full details are in the itinerary below.** **Accessibility** Wilderness Union is committed to making our adventures as accessible as possible. If you wish to make an accommodation request relating to a disability or provide feedback, please do so by sending an email to info@wildernessunion.com **Highlights** **The Grotto:** The peninsula's most famous natural feature: a limestone sea cave with turquoise water and a rock window looking out over Georgian Bay. **Stormhaven Coastline:** A stretch of cobble beach with wide open views across the bay, well past where most day hikers turn around. **Fall Colour on the Escarpment:** Peak autumn colour against the Niagara Escarpment's pale limestone cliffs, a contrast you don't get anywhere else on the Bruce Trail\*\*.\*\* **Event cost: $140+HST. Transportation is included in the cost of the adventure. Please register [here.](https://www.wildernessunion.com/adventures/bruce-peninsula-26)** **About Wilderness Union** Wilderness Union is deliberate about building an outdoors community that connects you to the life-changing magic of the outdoors and helps you find your people. Members range from 20-40 years old. The group is a mix of GTA locals and newcomers to Toronto from within Canada and abroad. Attendance numbers on Meetup don't reflect our actual event attendance - we typically have 15-20 community members at each event. Large enough that there's someone new to meet but small enough that it's not overwhelming! ***Learn more at our website [www.wildernessunion.com](https://www.wildernessunion.com/)***

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1 attendee
🏕️ 3 Days, 6 Spots: Algonquin Park Awaits

🏕️ 3 Days, 6 Spots: Algonquin Park Awaits

Fri, Oct 16, 6:00 PM
From High Park Hiking Club
4.8

Get your boots ready—we’re heading into the heart of [Algonquin Provincial Park](https://www.ontarioparks.ca/park/algonquin) for a 3-day backcountry hiking extravaganza. Expect stunning views, crisp forest air, brilliant colors and three full days of asking each other, *"Does anyone know which way is North?"* **The Catch:** * **Cap:** Strictly limited to **6 hikers** (because 7 is a crowd, and 8 requires a larger campfire circle). No camping just glamping in a hotel. * **Duration:** 3 days of pure trail bliss. * **Date:** October 16-18. That’s Friday to Sunday * **Details:** Top secret for now. Trail maps, packing lists, and more will drop as soon as you lock in your spot. First 6 to RSVP by September 14th get a ticket to the trail. Hit reply to claim your spot before the bears beat you to it on this luxury autumn trek 🌲🥾 🍂

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6 attendees

Crothers Woods to St Clair via Vale of Avora. Moderate. 2.7

Sun, Oct 25, 1:30 AM
From Hong Kong Hiking Meetup香港遠足覓合團
4.8
4 attendees
430kMonthly events
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60mMembers
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4.5App store rating
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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.