Challenging Hikes Toronto

🥾 Silent Lake Hike

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)** **Our Instagram: [@try_toronto_](https://www.instagram.com/try_toronto_)**

Hike with Lorne O

Hello Fall Colours: Dorset Hike & Lookout Tower

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/dorset-hike-and-lookout)** **Not every good trail makes it into a guidebook, and this hidden gem sure hasn't.** Tucked just southwest of Algonquin, it's a route we keep close for our members: rolling rock outcrops, quiet beaver ponds, and wide ridges that open into sweeping views when you least expect them. In September, the whole forest turns to a radiant display of red, orange, and gold; the kind of colours that makes you stop mid-stride. Welcome to fall in Ontario. We'll cover 7.5 km at a comfortable pace, with plenty of time to take it in before stopping for lunch at one of the best views on the route. It's a moderate hike, and a solid choice if this is your first time out on trail. From the trailhead, it's a short drive to Dorset. The tower was first built in 1922 as a fire lookout and rebuilt in 1967 into the structure that stands today. Climbing to the top puts you level with the treetops and gives you a panorama of the hills and lakes around Lake of Bays, all dressed in their fall colours. It's one of Ontario's most recognizable lookouts, offering a totally different perspective after a morning spent within the tree canopy. **Please note that anyone not taking the WU transportation will need to purchase their own tower access pass.** ‍ **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](mailto:info@wildernessunion.com) **Highlights** **The Lookout Tower Climb:** The observation deck sits 142 metres above Lake of Bays, with a 360 degree view over the surrounding hills and lakes. **A Trail Off the Map:** A quiet, little-known route kept for Wilderness Union members, far from the lineups that build up around Dorset in the fall. **Fall Colours:** Red, orange, and gold scattered across the Canadian Shield. **Event cost: $75+HST (for explorer members) + $60 optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/dorset-hike-and-lookout)** **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/)***

Dinner at Bale Kapampangan (after Bathurst Street hike)

This is a companion event for the [Jewish and Filipino Bathurst Street hike](https://www.meetup.com/hike-to-eat/events/316245847/). You don't have to do the hike to join this, but it's more rewarding if you do. Pampanga is regarded as the culinary capital of the Philippines and [Bale Kapampangan](https://balekapampangan.ca/) is the place to indulge in its cuisine. The Kapampangan palate is adventurous and quite different from the rest of the Philippines. Snails, frogs, blood, monitor lizards, and dogs are fair game. Thankfully, you won't find the latter two at this restaurant. Their menu is still unusual compared to other Filipino restaurants in Toronto. They've even introduced lobster dishes, in a nod to its Canadian home. Most dishes are large and meant for sharing. Bale Kapampangan does not take reservations on weekends, so we'll arrive before the dinner rush. Although the restaurant is aware of our arrival, **there's no guarantee there will be enough seats**. You might have to wait or we might split to different restaurants. RSVP closes 1 day before the event. If there are many people on the waitlist, we may increase the attendee limit. **Payment** * The $5 event fee is a deposit. It will be refunded when you show up for the event. * If there are spots available when you sign up, you have 24 hours to e-transfer the fee to globaltorontoeats@gmail.com * If you're on the waitlist for the restaurant event, you don't have to pay yet. After you've made it off the waitlist, you have 24 hours to pay. Remember to check your junk mail and Meetup notification settings so that you know when you've snagged a spot. * When sending the e-transfer, please add a note that mentions your Meetup.com name. * If you do not pay in time, you will be removed from the attendee list. The spot will be given to the next person on the waitlist. **Cancellation and refund policy** * You can cancel and get a full refund 5 calendar days before the event. For example, if the event is on Friday 7pm, you can cancel without penalty anytime before the preceding Sunday 11:59pm. * No refunds within 5 calendar days of the event, unless someone can be found to take your place. * Full refund if the event is cancelled, rescheduled, or you can't get a seat at the appointed time.

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

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

Wilder Series: The Provoking Lake Loop

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/provoking-lake)** **Most people take two days to walk around Provoking Lake. We are doing it in one.** This one's part of our Wilder series, our lineup of challenging adventures for those chasing bigger, more grueling and more rewarding days out. We’ll be taking on Loop 1 of the Algonquin's Highland Backpacking Trail, The trail circles Provoking Lake through classic Algonquin forest, roots, rock, and enough elevation change to keep your attention the whole way around, covering 21.5km by the time we're back at the car. You will pass a couple of lookouts over the lake and the surrounding hills, and long stretches where the loudest thing around is a woodpecker or your own footsteps. Backcountry campsites dot the shoreline the whole way around, a quiet preview of what a multi-day trip on this trail could look like down the road. Twenty one kilometres of Algonquin backcountry, done in a day. Are you up for it? **Due to increased demand for daily vehicle permits in fall, all members will be required to take our transport for this adventure. The cost of transport is included in the cost of this adventure.** ‍ **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](mailto:info@wildernessunion.com) **Highlights** **Provoking Lake Lookouts:** A couple of clearings along the loop open up over the lake and the surrounding hills. **A Real Physical Test:** 21km and over 800 metres of climbing in a single day. Come ready to work for it. **Wildlife Country:** Moose and loons are regulars around Provoking Lake, keep your eyes open. **Event cost: $130+HST (for explorer members)** **Register [here.](https://www.wildernessunion.com/adventures/provoking-lake)** **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/)***

Dundas Peak and Tews Falls Hiking

Join our WhatsApp group [https://chat.whatsapp.com/F7838OJWfkiAlMEyNffVfZ](https://chat.whatsapp.com/F7838OJWfkiAlMEyNffVfZ) * **Trail Information** Hiking Dundas Peak and Tews Falls in the Spencer Gorge Conservation Area offers a scenic 1.8-mile trail featuring the 41-metre-high Tews Falls and panoramic gorge views, with visits now operating on a first-come, first-served basis as advance reservations are no longer required. Location\*\*:\*\* 590 Harvest Road, Dundas, Ontario. Length\*\*:\*\* About 1.8 miles (2.9 km) round trip . Difficulty\*\*:\*\* Easy to moderate with some short stair sections and small hills. Time\*\*:\*\* Roughly 25 to 30 minutes of walking each way between the parking area, Tews Falls, and Dundas Peak. **Key Highlights** Tews Falls: A stunning ribbon waterfall standing at 41 metres tall with dual viewing platforms. Dundas Peak: A high rocky lookout point providing sweeping views over the city of Hamilton and the Dundas Valley. **Book Carpool or Driver** * [https://www.extremelyshy.com/toronto&f66v6t](https://www.extremelyshy.com/toronto&f66v6t) * **Carpool**: You will be assigned to a vehicle. Let the driver scan your QR code to access your carpool service. * **Driver**: You will receive driver instruction in your confirmation email. Scan the QR code from the passenger to provide your carpool service to get paid **What’s included** * Gas, Vehicle use, Driver effort. * Split bill with your vehicle people if any other expense is exist. **Meeting and Pickup** * Meeting Time: 8:00 AM * Meeting Point: In front of Tim Hortons Dufferin Station 1094 Bloor St W, Toronto, ON M6H 1M5 * End Time: 6:00 PM * End Point: This activity ends back at the meeting point. **Refund Policy** * Refund Policy: Not refundable except if the event is canceled, rescheduled. Contact us by the end of the day. **Liability** * The organizer and any/all assistant organizers and other attendees are in no way responsible and liable for your personal safety and health state, before, during, and at any time after this event. * You acknowledge you are solely responsible for your health, safety, and well-being before, during, and at any time after the event as stated previously. * All attendees shall forever hold harmless the organizers and other attendees and unconditionally waive any liabilities resulting from attending and/or participating in this event.

Food evolution in poorly-planned neighbourhoods (6 km)

**Attendance policy is enforced for this hike**. See below for details. Liberty Village and CItyPlace are two high-density neighbourhoods that are examples of how not to do urban planning. Thankfully, some things have gotten better, like the presence of some good restaurants. This hike will highlight some of the better food options and architectural gems in these neighbourhoods. End the hike at a trio of casual restaurants: classic burgers, grilled chicken, or Thai street food—all the top of their kind in Toronto. **Highlights** 1. Haydn's Acaí at Stackt Market (depart 6:30 pm) 2. Puente de Luz 3. Mailo's 4. Canoe Landing Community Recreation Centre (depart 6:55 pm) 5. Parade condos 6. Roywoods 7. Fort York / The Bentway 8. Garrison Point condos / Garrison Crossing 9. bb.q Chicken / Burgers n' Fries Forever 10. Liberty Village Park (depart 7:35 pm) 11. Thindi Cafe / Chiang Mai Restaurant / Aloette Go 12. Wilbur's Taco Shop 13. Toronto Carpet Factory 14. Thai Barn Na / Burger Drops / Mozy's (arrive 8:05 pm) **Neighbourhoods** Liberty Village > Fort York > CityPlace **Map** [https://www.google.com/maps/d/edit?mid=1cTd7g0hRwCk-7OkO-O3UhhJRb4QBQYM&usp=sharing](https://www.google.com/maps/d/edit?mid=1cTd7g0hRwCk-7OkO-O3UhhJRb4QBQYM&usp=sharing) **How it works** Hike starts punctually. Late or can't do the whole route? Meet us at scheduled checkpoints. We'll browse many food places but won't linger long. See the route in advance, organize takeout, then pickup along the way. Not sure what to try? Join our omakase for $5, which gives a tiny sample from different restaurants. Payment on the day of event by cash or e-transfer to [globaltorontoeats@gmail.com.](http://globaltorontoeats@gmail.com.) No refunds after orders are placed. Details of sampled food will be uploaded after the hike. Limited cutlery provided. Highly recommended to bring cutlery and containers for omakase and bringing back leftovers. See our [About section](https://www.meetup.com/hike-to-eat/) for more info. **Attendance policy** Please check in with an organizer when you arrive. 24 hours before the hike, we'll note who is on the confirmed list. Those that don't show up will be marked as no-show. Repeat offenders will be banned. Please change your RSVP if you can no longer attend. If you got off the waitlist less than 24 hours before the event, you won't be considered a no-show.

🌳🚶‍♂️ Eglinton West Trail & Mimico Creek + Swiss Chalet 🍗! 12KM

**🌳🚶‍♂️ Eglinton West Trail & Mimico Creek + Swiss Chalet 🍗** Golden trails, sparkling creek, great conversation… and Swiss Chalet after 🍗. We’re walking **Eglinton West & Mimico Creek** this weekend — once it’s over, it’s gone. Meet awesome people, get fresh air, and make memories you *won’t* get sitting at home 💬☀️. 📱 Don't forget to join our **WhatsApp Group – [CLICK HERE](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** **📍 Meetup Details** 🚌 **Start:** We’ll begin by taking the **73 Bus** to Eglinton West. 🚶‍♀️ **Route:** Follow the city trail until we reach Mimico Creek, take a short park break 🌳, then continue back to **Royal York Subway Station** 🚇. 📌 **Location:** Inside Royal York Subway Station — by the stairs on the bus platform. Look for me in my 🦌 Moose Hat! ⏰ **Time:** We leave with the **10:55am bus** — I will only wait until departure. 💵 **Fee:** $5 cash 💰 or e-transfer to **mathewmaclean@hotmail.com** **🎒 What to Bring:** 💧 Water 👟 Good walking shoes 🥪 Snack 🚻 Bathroom stop before you arrive (there *may* be facilities on the walk, but not guaranteed) 🏁 **End Spot:** Back at Royal York Subway Station 🕒 **Leaving Time:** Anytime you like — your pace, your choice! **⚠️ Notes:** * Plans can change — please check for possible cancellations 🔔. * You can **just show up** if you’re not sure until the last minute. 💬 This group is open to *everyone* — singles, couples, social butterflies 🦋, and anyone who wants to meet great people. We also host 🎥 movies, 🥾 hikes, 🎭 arts & culture outings, and more.**[!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** 📩 **Organizer:** Mathew — post a message on the wall or email **torontomoviesandoutings@hotmail.com** for questions. **Come for the trails.** **Stay for lunch.** **Leave with a new connection — and maybe a new friend.** 🌳🍦💛

Bus Hike: Terra Cotta (New Hikers/Families Welcome)

New Hikers (but all are welcome) are invited to join me on a 10 km Introductory Level Bus Hike on the Toronto Section of the Bruce Trail around Terra Cotta less than an hour from Toronto. Expect some downhill/uphill and tree roots but nothing too rocky or challenging. We'll be following behind the hikers completing the club's annual two day E2E hike. There will be the option of a short out and back hike on the Walking Fern Side Trail at the end. After the hike we'll drive to Spirit Tree Estates Cidery that offers pizza and baked goods and a country store. Hopefully the weather cooperates so we can sit on the picnic tables outside. Optional dropout at 5 km. Hiking boots are recommended. Beginners and families welcome. \*\* Registration opens Sun Aug 30 at 8:00 PM. You must register and prepay the bus fare on the Bruce Trail Conservancy Website $25 Members/$32 Non-Member Children Under 10 $12/$14 (bus fares are non-refundable and the hike goes rain or shine) Registration link: [https://hikes.brucetrail.org/event/bus-hike-terra-cotta-new-hikers-families-welcome/2026-09-12/](https://hikes.brucetrail.org/event/bus-hike-terra-cotta-new-hikers-families-welcome/2026-09-12/)

North Humber River Long Walk - 16KM (You might see a deer!)

### 🌿 North Humber River Walk – 6th Annual! 🌿 We’re back for our **sixth year in a row** with this incredible walk — and it has become a true fan favourite! The North Humber River trail is one of Toronto’s most peaceful and nature-filled walks. It’s a longer walk, but that’s part of what makes it so rewarding. You’ll get out of the city, follow the river, explore beautiful natural areas, and see just how far you can go when you give yourself the chance. This walk is about challenging yourself just a little — you'd be surprised how far you can go! If you don't want to complete the entire walk, that's totally okay. You can leave along the way, and I can help you find the nearest way back toward public transit. We'll finish with a quick stop at Tim Hortons before heading back toward Kipling Station. ### 📲 Stay Connected Don't forget to join our **WhatsApp Group – [CLICK HERE!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** It's a great way to get updates, connect with other members, and stay informed about the event. *** ### *** ### 📍 Meetup Details 🕙 **Meetup Time:** 10:00 AM 🚌 **Bus leaves:** 10:06 AM sharp 📍 **Meetup Spot:** In front of the Information Booth at Kipling Subway Station Bus Terminal 🫎 Look for Mathew in the Moose Hat! 🚌 **Bus:** 927B Highway 27 Express to Steeles via Humber College ⚠️ **PLEASE BE ON TIME.** If you miss the bus, you will miss the group. We cannot wait for late arrivals. *** ### 🚗 Driving / Meeting Us at the Trail If you live closer to the trail or prefer to drive, **you can meet us at Humberline Park**. 📍 **Meeting Point:** Humberline Park, by the bathrooms ⏰ **Meeting Time:** Approximately **10:35 AM** Please look up directions to Humberline Park before leaving and give yourself plenty of time to get there. 🚗 **Parking:** Parking availability in the area can vary, so please check the parking situation before coming. ⚠️ **Important:** If you drive to Humberline Park, **you will need to arrange your own transportation back at the end of the walk.** We do not finish the walk back at Humberline Park. You may need to use Uber, a taxi, or public transit to get back to your vehicle. If you're meeting us at the park, please make sure you are there and ready to walk by 10:35 AM. Once we arrive, we'll be continuing with the group. *** ### 💵 Meetup Fee **$5 cash in person or e-transfer** 📧 **[mathewmaclean@hotmail.com](mailto:mathewmaclean@hotmail.com)** This small fee helps support the group and keeps events like this running. Thank you for supporting the community! *** ### 🌲 What to Expect 🚍 A 40-minute bus ride to the starting point near Humber College 🌿 A peaceful walk along the North Humber River 🦌 Opportunities to spot deer, birds, and other wildlife ☕ Two rest stops along the route 🥾 A longer walk that will give you a chance to challenge yourself 🍩 A final stop at Tim Hortons before heading back toward Kipling Station Some sections of this trail genuinely feel like you've left Toronto behind. It's one of those walks where the city slowly disappears and you're surrounded by trees, water, wildlife, and open space. *** ### 🧳 What to Bring 💧 Water 👟 Good walking shoes — some sections may be uneven 🥨 A snack 🧴 Sunscreen 🎒 A small backpack *** ### 👥 Who Is This For? This group is for anyone who wants to get outside, explore Toronto, and meet people along the way — singles, couples, newcomers, longtime Torontonians, and everyone in between. We host: 🎬 Movies 🚶 Walks & hikes 🎭 Arts & culture 🍽️ Restaurants 🎤 Karaoke …and plenty more! The activity is the **container**. The people you meet and the connections you make along the way are the real experience. 💛 *** ### 💛 A Few Notes You're welcome to join us even if you're deciding at the last minute. If you need to leave the walk early, that's okay — just let me know and we'll help you figure out the best way to get back toward transit. Sometimes things happen and events may need to be cancelled or changed. Please keep an eye on the event page for updates. *** 👤 **Organizer: Mathew** 📧 Questions? Post on the event wall or email: **[torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com)**

Taylor-Massey Creek & Don River Walk + Ice Cream 🌳🍦9KM

## **Taylor-Massey Creek & Don River Walk + Ice Cream** 🌳🍦 **Taylor-Massey Creek** is a tributary of the Don River, winding its way through Scarborough and East York before meeting the Don. Named after two prominent Toronto families, the Taylors were well-known for owning and operating the historic Don Valley Brick Works. This walk takes us along the scenic **Taylor-Massey Creek Trail**, through the **Don Valley**, and ends with a challenging hill climb before rewarding ourselves with **ice cream at Dairy Queen**. If ice cream isn’t your thing, you can continue with the group toward Broadview Station. 📲Don't forget to join our **WhatsApp Group – [CLICK HERE!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** *** ### **🕰 Meetup Details** **Start Location:** Outside the main entrance of Victoria Park Station (on Victoria Park Road). Look for me in my Moose Hat 🦌. **End Point:** Near Broadview Station *(we will not be returning to Victoria Park)*. *** ### **💵 Meetup Fee** **$5 cash in person** or **e-transfer** to: **mathewmaclean@hotmail.com** *** ### **🥾 What to Bring** * Water 💧 * Comfortable walking shoes 👟 * A snack 🥪 * Bathroom breaks are limited — there’s only one near the very end of the walk. *** ### **🚶 Pace & Flexibility** We’ll be leaving Victoria Park at a steady walking pace, but you can leave anytime you like. *** ### **Please Notes** * Occasionally events need to be cancelled — please check for updates before heading out. * You can **RSVP in advance or just show up** if you’re unsure you can make it. * This group is open to **everyone** — single, coupled, shy, social, new in town, or a long-time local. We also host **movies, hikes, arts & culture, restaurants**, and more — come be part of it! 📧 **Contact Mathew (Organizer):** Post a message on the wall or email **torontomoviesandoutings@hotmail.com** **Come for the trails.** **Stay for the ice cream.** **Leave with a new connection — and maybe a new friend.** 🌳🍦💛