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Challenging Hikes Toronto

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🌲🥾 CROTHERS WOODS TRAIL HIKE & DAIRY QUEEN STOP 🥾🍦

🌲🥾 CROTHERS WOODS TRAIL HIKE & DAIRY QUEEN STOP 🥾🍦

Sun, May 31, 3:00 PM
From No Such Thing As Bad Weather Walking & Hiking Group!
4.8

🌲🥾 **CROTHERS WOODS TRAIL HIKE & DAIRY QUEEN STOP** 🥾🍦 Real Trails, A Solid Climb & An Ice Cream Finish Toronto doesn’t have many *true* hiking experiences — but this is one of them. Join us for a more active, nature-focused walk through Crothers Woods, one of the city’s best spots if you’re looking for something that actually feels like a hike. This isn’t your typical flat city stroll. There are hills, forest paths, and a proper climb — especially at the end (Pottery Road 👀). But don’t worry… we’ve got a reward waiting. This is not a formal tour. It’s a social hike — a bit more effort, a bit more nature, and a great group to do it with. 📲 **Join Our WhatsApp Group:**[ Click here to join](https://chat.whatsapp.com/DRFTkxRlHS4B3IL1lMleUd) \*\*\* **🚶‍♂️ What We’ll Do** We’ll start at Broadview Station and head south along Broadview before making our way down Pottery Road into the Don Valley. From there, we’ll connect to the Don Valley trails and enter Crothers Woods, where we’ll hike through forested paths and take a short break along the way. After the hike, we’ll make our way back — finishing with the climb up Pottery Road (the final challenge 💪). And then… we reward ourselves with a stop at Dairy Queen for some well-earned ice cream. 🍦 We’ll end back near Broadview Station. \*\*\* 🌦️ **Weather & Expectations** This hike happens rain or shine. Please come prepared — trails may be muddy, and conditions can vary. This is a slightly more challenging walk than most of our events: ✔️ Uneven trails ✔️ Some hills ✔️ One bigger climb at the end Good footwear is important. Also — this is NOT a guided or historical tour. It’s about movement, nature, and being social. \*\*\* 🧢 **Meetup Details** 📍 Meetup Location: Outside Broadview Subway Station 🫎 I’ll be wearing my Moose Hat ⏰ Meetup Time: 11:00 AM I will only wait 5 minutes. Early is on time. On time is late. We’ll head out promptly. End Point: Broadview Subway Station \*\*\* 🎟️ Meetup Fee: $5 cash in person or e-transfer to 📧 \*\*[mathewmaclean@hotmail.com**](http://mathewmaclean@hotmail.com%2A%2A/) This helps support the group and allows us to keep hosting events like this. Thank you for supporting community! 💖 \*\*\* 🎒 **What to Bring** Water Good hiking/walking shoes (important!) A snack Weather-appropriate clothing (trail-ready 🌧️🌿) Optional: cash/card for ice cream 🍦 **Please also use the washroom before arriving, as stops are limited.** \*\*\* 🌈 **Who Is This For?** This group is open to anyone who wants to be social and make friends — whether single or not. **We also host:** 🎬 Movies 🚶 Walks & hikes 🎭 Arts & culture outings 🍽️ Restaurant gatherings There’s always something happening. \*\*\* **REMEMBER:** You’re welcome to just show up on the day if you’re unsure about your schedule. And as always, sometimes plans shift and events may need to be canceled — please keep an eye on updates. \*\*\* 👤 Organizer: Mathew Questions? Post on the event wall or email 📧 [torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com) Come for the trail. Stay for the challenge. Leave feeling like you actually *earned* that ice cream. 🍦🌲✨

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25 attendees
🍁Niagara Falls Hiking Day Trip — Trails and Dinner !!

🍁Niagara Falls Hiking Day Trip — Trails and Dinner !!

Sat, Jun 13, 12:15 PM
From No Such Thing As Bad Weather Walking & Hiking Group!
4.8

🍁 **Fall Niagara Falls Hiking Trip** 🌦️ **Rain or Shine!** The adventure goes on — whether it’s golden sunshine, crisp autumn air, or a little mist from the Falls (it *is* Niagara, after all!). \*\*\* 🥾 **About the Trip** Let’s escape the city for a full fall day of fresh air, friendship, and breathtaking scenery! We’ll explore the *natural* side of Niagara Falls — less tourist traps, more trails, trees, and pure wonder. We’ll meet outside the **Fairmont Royal York (Front St. W)** in the morning, hop on the **GO Train**, and head to **Niagara Glen Nature Reserve** for an afternoon hike among ancient boulders and the turquoise waters of the Niagara River. This hike includes stairs (about three flights) and uneven terrain — so bring your comfy hiking shoes or sturdy runners (flip-flops will cry). \*\*\* 🌲 **The Trail Experience** The Niagara Glen is a hidden gem — carved out of the gorge thousands of years ago. We’ll follow winding forest paths, stop for photos, and take in the beauty of fall leaves glowing against the mighty river. It’s about 4 km total, with lots of opportunities to pause, chat, and soak in the view. ⚠️🥾 **IMPORTANT: HIKE EXPECTATIONS – PLEASE READ CAREFULLY** 🥾⚠️ This is a **real hiking trail**, not a casual walk. You need to arrive knowing you can: ✔️ Walk for an extended period of time ✔️ Handle uneven terrain and elevation (including the climb back up) ✔️ Keep a steady group pace without frequent stops This is **not the time to test your fitness level** or “see how it goes.” If you are unsure whether you can complete the hike, please sit this one out. 👉 If someone is unable to keep up, they may be asked to turn back or continue at their own pace. The group will not be stopping or slowing down significantly, as it impacts the experience for everyone. This is about keeping the group safe, on track, and enjoyable for all. \*\*\* 🍔 **Dinner & Cozy Evening** After the hike, we’ll head to **Chuck’s Roadhouse** on Clifton Hill for a relaxed dinner (everyone pays for their own meal). It’s friendly, affordable, and always buzzing after a big day outdoors. **Please Note -** This place is not the most vegetarian friendly place. If you will not be joining us because of that reason. Please let me know as will be trying to make reservations. This should not be something you tell me lat minute. \*\*\* 🎇 **Niagara Falls** After dinner, we’ll stroll down to the Falls and enjoy the rolling sound of the majestic falls. \*\*\* 💲 **Meetup Fee:** 💵 **$5 cash at the event** *or* 📲 **E-transfer anytime (before or on the day)** to \*\*[mathewmaclean@hotmail.com**](http://mathewmaclean@hotmail.com%2A%2A/) (You can pay either way — easy!) \*\*\* 🚆 **TRANSPORTATION REQUIREMENT** To keep things simple and organized: 👉 **Only those traveling together on the GO Train with the group will be able to participate.** We will not be meeting people at Niagara Falls. This helps avoid confusion, delays, and coordination issues, and keeps the group moving smoothly from start to finish. 🚆 **Travel Details (approximate)** * **8:15 AM** – Meet at the main doors of the Fairmont Royal York (Front St. W). I’ll be wearing my *Moose Hat!* 🫎 * **8:30 AM** – Depart * **9:03 AM** – GO Train to Niagara Falls * **11:25 AM** – Arrive at Niagara Falls * **12:30 PM** – Start hike at Niagara Glen * **4:30 PM** – Dinner at Chuck’s Roadhouse * **6:00 PM** – Walk Down to the Falls * **8:00–9:00 PM** – Return train to Toronto *GO schedules may shift slightly — I’ll update the group closer to the date.* \*\*\* 🎟️ **Tickets & Gear** Please purchase the **GO + WEGO Combo Ticket (round trip $20)** before the trip you can buy this one day before. 👉 [CLICK HERE to buy your pass](https://www.niagaraparks.com/visit-niagara-parks/plan-your-visit/deals-toronto/) Bring: 🥾 Comfortable shoes or boots 💧 Water & snacks 📸 Camera or charged phone (you’ll want photos!) \*\*\* 📲 **Join Our WhatsApp Group:**[ Click here to join](https://chat.whatsapp.com/DRFTkxRlHS4B3IL1lMleUd) \*\*\* ⚠️ **Important Notes** This is a full, active day — lots of walking, laughing, and exploring. Open to everyone — singles, couples, or friends. You can *just show up* the day of if you’re unsure in advance. \*\*\* 👤 **Organized by Mathew** Questions? Post on the event wall or email: \*\*[torontomoviesandoutings@hotmail.com**](http://torontomoviesandoutings@hotmail.com%2A%2A/)

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

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

Wed, Jun 3, 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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5 attendees
Another Opportunity to Learn New Skills - Trekker Training

Another Opportunity to Learn New Skills - Trekker Training

Sat, Jun 6, 1:00 PM
From These Boots Are Made for Hiking
4.8

**Meet up Point:** Algonquin Park - Maggie Lake Entrance **Two Days...sat and sun** **Fee for Trekking Training: $99.** Because it was so much fun, we are offering Trekker Training again in June! We want you (and all our members) out Trekking. Don't give up your Sunday hikes, but hey it's time to up your hiking game! Which is why we are offering skills training for future trekkers so they can join in on trekking adventures outside of Ontario. There is a lot to learn to prepare for a multi day trekk, and we want you to be prepared. It is not just knowing what equipment to buy, how much to carry, tent set up, it's also food prep, attitude, and emergency skills and so much more! So, in order for you to ensure you have a safe and the very BEST trekking experience we are offering an overnight training experience. **Experienced Boots Trekkers feel free to hop in and show them how it's done!** We will cover in one weekend - * your weighted pack * pack pacing * water filtering * trail etiquette * safety * equipment must haves * first aid * atittude adjustment * fire starting * navigation * ...and more

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5 attendees
Feel the burn folks on this Bike Ride led by ITALO!

Feel the burn folks on this Bike Ride led by ITALO!

Sat, Jun 13, 1:00 PM
From These Boots Are Made for Hiking
4.8

**MEETUP POINT: Woodbine Park in front of the Beach Club - 1681 Lake Shore Blvd E** Join us for a 50km bike ride in the city. Don't worry it's flat! Led by Italo who is an experienced cyclist and leader, so you will be in good hands. It's lots of fun and not too far! The ride begins at Woodbine park and ends nearby for a social and lunch. (I'll keep you posted on where it will be.) Please come prepared with the right riding gear which means not a commuter bike. This wouldn't be a beginner bike ride. Bring lots of water and snacks. Helmets obviously a must! [https://ridewithgps.com/routes/53737876](https://ridewithgps.com/routes/53737876)

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57 attendees
Hike & Swim the Canadian Shield

Hike & Swim the Canadian Shield

Sun, Jun 7, 12:30 PM
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/mccrae-lake-hike-swim)** ***Join us for this peaceful, day-long getaway spent exploring the trails, forests and waters of McCrae Lake!*** Our morning begins with a gentle 3.5 km trek through the lush forest. These trails meander through and along the granite ridges that make the Canadian Shield so famous. We’ll eventually arrive at the famous Crow’s Nest Lookout with its amazing panoramic views of the lake and adjacent pine-covered hills. This is where we’ll stop to refuel and enjoy our lunch while soaking in the quiet atmosphere that you can only get when you get out of the city and into nature. After our meal, we’ll make our way down to the water’s edge for a few hours of pure relaxation. You can jump in for a swim in the clear lake water or simply find a smooth rock to lounge on and take in the rays. Once we’ve had our fill, we’ll finish the day by retracing our steps through the forest and heading back into the city. **Highlights** **Pristine Backcountry Swimming -** Escape the crowded city beaches to this amazing and secluded cool off spot. The water is refreshing and clear, providing the perfect reward after our morning hike. **Possible Wildlife Spotting** \- Otters\, bears\, beavers\, eagles and loons are just some of the creatures that call this area home\. You might even have a chance to spot some from a safe distance for a magical encounter\. **Panoramic Forest Views -** Look out from the famed Crow’s Nest panorama where you can see for kilometers across the green canopy and the shimmering blue waters. **Event cost: $60+HST (for explorer members) - $50 optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/mccrae-lake-hike-swim)** **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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4 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.