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Challenging Hikes Toronto

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🥾 Silent Lake Hike

🥾 Silent Lake Hike

Sat, Sep 19, 1:00 PM
From Try Toronto: Newcomers, Friends & Local Experiences

Escape the city and discover Silent Lake Provincial Park - peaceful forest trails, granite ridges, crystal-clear water, and beautiful viewpoints over one of Ontario’s few motor-free lakes. We’ll hike a 15 km loop at a relaxed pace with breaks for photos and enjoying the scenery. The trail is easy to moderate, but you should feel comfortable walking for 5-7 hours on uneven terrain with some hills and rocky sections. After the hike, we’ll relax at the beach for a snack or head to a nearby restaurant together. **☀️ What to expect:** • Guided 5-7 hours loop hike through Silent Lake Provincial Park • Beautiful forest trails and rocky Canadian Shield landscapes • Scenic lookouts over the lake • Plenty of photo opportunities • Friendly group and a relaxed pace ✨ **Price:** $65 - participants without their own transportation 🚶‍♀️ $40 - participants driving their own car 🚗 (without passengers) - promocode **SELFDRIVE** $25 - participants driving their own car 🚗 and willing to take 3+ passengers (driver pays for gas themselves) - promocode **DRIVEROFF** **Price includes:** guidance throughout the hike, light snacks and transportation coordination for participants without cars. 📍 **Meeting place:** Vaughan subway station ‼ **Difficulty**: Easy to Moderate **🙋‍♀️ Guide:** Kate - an ambassador for hiking and outdoor adventures in all seasons. She completed 124 km of the Camino in just 6 days. A coach and advocate for the idea that therapy can save everyone. And what could be more therapeutic than walks in nature?! **Register here or on [TryToronto website](https://trytoronto.org/events/silent-lake)**

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1 attendee

Hike with Lorne O

Sun, Oct 25, 3:00 PM
From Mosaic Outdoor Club of Ontario (GTA+)
4.7
5 attendees

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

Sun, Aug 30, 11:00 AM
From 2&4hr -Advanced Hikes TORONTO
4.9
7 attendees
HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

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

Wed, Sep 2, 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:** 1\~2 liters * **Extras:** Hiking pole (Highly recommended) * **Required Gear:** Hiking boots or Trail Runners with good grip, Headlamp, and [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
Epic #5 - The Lavielle Loop

Epic #5 - The Lavielle Loop

Wed, Sep 2, 9:00 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/epic-5)** ***Welcome to The Epics!*** ***Through this series, we will embark together on five of the most legendary and challenging adventures anywhere in Ontario.*** **History** Deep in the interior of Algonquin Park lies a chain of lakes that remains a bucket list trip for serious paddlers. The Lavieille Loop is a high-endurance expedition named after one of the most beautiful lakes in a park full of incredible scenery. This is a route of extremes: from the crystal-clear expanse of **Lake Lavieille** to the winding, moose-heavy waters of the **Crow River**, culminating in the legendary 5.5km **Dickson-Bonfield portage**, this is a true test of grit. This expedition is inspired by the Meanest Link, a legendary challenge created by our friends and partners at Algonquin Outfitters. Designed by Alex Hurley and Gord Baker as a tribute to AO’s founder, Bill Swift Sr., the Link was built to push the limits of exploration and self-reliance. While our loop covers a specific, scenic section of this historic network, we’ve designed this Epic to channel that same spirit of adventure and respect for the park’s heritage. Learn more about the history and the original route of the Meanest Link on the [Algonquin Outfitters website](https://algonquinoutfitters.com/about/meanest-link-history/). ‍ **What You Need to Know** This journey is a true ode to Algonquin Park. We’ve carved out a nearly 100km route, taking us from the massive waters of Lake Opeongo, along the winding Crow River, and into the remote reaches of Lake Lavieille before heading back down to Opeongo. By doing this in early September, we catch the park at its absolute best: the bugs are gone, the weather is beautiful, and the wildlife is active along the riverbanks. Awaiting us in the second half of our journey is the notorious Dickson-Bonfield portage. At over 5km,this is the longest single portage in Algonquin Park. It’s relatively flat but a huge challenge and, once you set your canoe down at Bonfield Lake, you’ll have earned your place among the most dedicated paddlers in the province. This trip requires a high level of fitness and a genuine willingness to embrace the challenge of a 5km trek with a canoe on your shoulders. For those willing to take on the challenge, this offers the most rewarding sense of accomplishment you can find on the water. **What's Included:** * *2 expert guides with advanced wilderness skills and medical training* * *Rentals for lightweight canoes, PFDs and paddles* * *All camp meals, cooking equipment and mess kits* * *All safety equipment (including first aid kits and water purification)* * *Tents and all the camping equipment you'll need (sleeping bags and pads are available for rent)* * *All permits and campsite bookings for the whole trip* * *A preparatory information session* * *Detailed trip plan with packing lists, maps and the indigenous history of the route we're following* * *Extensive planning to ensure your safety throughout the adventure* * *A custom, iron-on patch to immortalize your unforgettable adventure* ***Epics are mentally and physically demanding adventures, and participation isn’t automatically guaranteed. These expeditions require skill, determination and teamwork to get through.*** ***To help ensure a safe and rewarding experience for all, anyone who has not previously completed an Epic will need to fill out a short questionnaire so we can assess readiness together.*** ***Your level of fitness and outdoors experience will play a role in this process. Having certain adventures under your belt will ensure you have the right skills and preparation for these kinds of experiences. These include:*** * ***Any Wilder Series adventure, including the upcoming Wilder Loop*** * ***Any Survivalist Series adventure, including Introduction to Navigation or Cold Exposure*** * ***Canoe Foundations Clinic*** * ***Hilton Falls Mega*** * ***Any other adventure with 4 or 5 star difficulty*** ***If you register for an Epic and are not approved, you will receive a refund in full.*** **Highlights** **An Epic Challenge -** Our longest and most ambitious epic will be the ultimate reward. **Dickson-Bonfield Portage -** The legendary portage spans 5.4km and is the longest single carry in the park. ‍**Secret Lake Sanctuaries** \- True crown jewels of the Algonquin interior\, there are no easy routes to the lakes we will be seeing\, which keep them incredibly quiet and pristine\. **Event cost: $1185+HST. $50 optional transport also available. Please register [here.](https://www.wildernessunion.com/adventures/epic-5)** **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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2 attendees
Short and Fast Fitness Hike – st. Clair Stn – (7km @ 6.5km/h) – L4 (Hard)

Short and Fast Fitness Hike – st. Clair Stn – (7km @ 6.5km/h) – L4 (Hard)

Mon, Aug 31, 10:30 PM
From Ready, Set, Trail
5.0

Join us for a brisk, energizing hike along the scenic David A. Balfour and Beltline Trails The Hike will Start and End at **[st. Clair Stn](https://maps.app.goo.gl/YMyW15weKdHeWPmQ6)** We'll maintain a steady pace of about **6.5km/h** over roughly **7km**, focusing on building endurance and improving cardio. This hike is recommended for anyone who can maintain a strong, steady pace and is looking to build hiking endurance and improve cardio fitness. The hike will go ahead rain or shine, with the route adjusted as needed based on weather conditions. **Distance & Duration:** * **Length of hike:** 7 km * **Event duration:** \~1.5 hours * **Difficulty level:** L4/Hard - due to sustained brisk pace over uneven terrain **What to Bring:** * **Water/Snacks:** 0.5 liter of water * **Required Gear:** Hiking boots/Trail Runners **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 **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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1 attendee
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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.