Challenging Hikes Toronto

Hike with Lorne O

🥾 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 - SOCKS - BEER (Bermuda Triangle)

Barbecue and Hike through Tommy Thompson Park.

Location: Meet at the entrance of Tommy Thompson Park -Leslie Street Spit **It's time to have some fun!** What better way to celebrate the end of Summer with a barbecue by the lake. Join us for burgers and drinks **under the tents** and on the water at Ashbridges Bay for burgers and drinks! ($10. For a burger and drink.) After a 8km hike (with some fun things happening along the way) at Tommy Thompson Park we will head to Ashbridges Bay for burgers- veggie and meat. Feel free to bring alcoholic beverages, and board games - We will have a beach ball. Tommy Thompson Park is a man-made urban wilderness and wildlife sanctuary built on the Leslie Street Spit, stretching 5 kilometers to Lake Ontario. Managed by the Toronto and Region Conservation Authority, this unique park offers a peaceful escape from the city with a mix of wetlands, meadows, and trails. A unique place near downtown Toronto to experience nature, and *one of the best places for bird-watching in the city*, with more than 300 recorded species!

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/)***

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/)***

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.** 🌳🍦💛

🌊 Hamilton Waterfront & 🌿 Cootes Paradise Trail Adventure- 2 Meetup Times!

# 🌊 Hamilton Waterfront & Cootes Paradise Trail Adventure Join us for a day outside Toronto as we head to Hamilton to explore the waterfront and the beautiful trails of Cootes Paradise. We'll begin along the Hamilton waterfront before making our way into Cootes Paradise, where we'll trade city streets for wooded paths, natural scenery, and a little bit of adventure. There are some hills and sections of uneven trail, so come prepared to walk — but that's part of what makes this such a great day out. This is a social adventure, not a formal tour. We're here to explore somewhere different, get some exercise, enjoy the scenery, and most importantly, spend time together. Don't forget to join our **WhatsApp Group – [CLICK HERE!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** *** ## 🚆 Getting to Hamilton ### Meetup Location #1 — Toronto **Outside the Fairmont Royal York facing Front street. This will be the ONLY Meetup spot for this location.** **Meetup: 9:00AM...we will only wait 15mins** **Departure: 9:30 AM sharp** Look for me in my Moose Hat. We'll take the GO Train from Union Station to West Harbour GO Station. Please be on time. Once the train leaves, you will not be able to catch up with the group. **GO Train Cost:** Approximately $10 for the Weekend & Holiday One-Day Pass. You can get your pass a week before - [CLICK HERE!](https://www.gotransit.com/en/partners-and-promotions/weekend-passes-with-go) ### Meetup Location #2 — Hamilton **Bayfront Park Parking Lot** 200 Harbour Front Drive We will meet near the flag polls. **Meetup: 11:00 AM** **We leave for the walk at 11:15 AM.** If you're driving or already in Hamilton, this is the place to meet us. *** ## 🌿 The Walk We'll explore the Hamilton waterfront before heading into Cootes Paradise. Expect: * Waterfront views * Forested trails * Natural scenery * Some hills * A few uneven or off-road sections * Plenty of time to chat and enjoy the day This isn't a race. We'll keep a steady pace, but you should be comfortable walking for several hours. *** ## 🍔 After the Walk After our hike, we'll head over to **Hutch's Harbour Front** for some ice cream. You can join us for or you're welcome to head home whenever you'd like. **Return GO Train:** We expect to catch either the **2:23 PM or 3:23 PM** train, depending on how the day goes. You are also welcome to stay in Hamilton longer and make your own way home later. *** ## 💵 Meetup Fee **$5 cash in person or e-transfer** **[mathewmaclean@hotmail.com](mailto:mathewmaclean@hotmail.com)** This fee helps support the group and allows us to continue creating events like this. *** ## 🎒 What to Bring * Water * Comfortable walking shoes * A snack * Sunscreen * Weather-appropriate clothing * Money for lunch and transportation *** ### A Few Notes You can RSVP in advance or decide 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. This group is open to anyone who wants to get outside, explore the city and surrounding areas, and meet people along the way — whether you're single, coupled, new to Toronto, or have lived here your whole life. We also host movies, walks, hikes, arts & culture outings, restaurants and more. **Organizer: Mathew** Questions? Post on the event wall or email: **[torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com)** ## 🌈 The Point of the Day The trail is the reason we get outside. The adventure is the reason we go somewhere different. But the people are the reason we keep coming back. **Come for the waterfront.** **Stay for the adventure.** **Leave with a new connection — and maybe a new friend.** 🌊🌿

Jewish and Filipino Bathurst Street + blind bagel tasting (6.75 km)

Bathurst Street is the historic home of Jewish communities in Toronto, starting with Kensington Market, then moving north to St Clair Ave West and then all the way to Richmond Hill. While we won't hike the whole street, we'll visit the heart at Bathurst St and Ranee Ave. With several bagel bakeries around, let's do a blind tasting to find the best. Close by, a Little Manila has developed around Bathurst St and Wilson Ave. It's not the only Filipino hub in Toronto but it's the most famous one. Wander through carinderias (hot tables) and grocery stores. **Highlights** 1. Bathurst and Lawrence northeast corner (depart 2:30pm) 2. United Bakers Dairy Restaurant 3. Phat Kaphrao 4. Bubby's New York Bagels / Haymishe Bakery / Savours Fresh Market 5. FK Dulce Bakery / Nozomi / Gryfe's (depart 3:10pm) 6. Grodzinski Bakery / Kosher City Plus / Tinuno / Soul Bagel 7. Shaarei Tefillah 8. Bathurst-Wilson Parkette (depart 3:45pm) 9. Wilson's Haus of Lechon / Bagel World / Harina Bakeshoppe 10. The South African Store 11. Richmond Kosher Bakery 12. Beth David Synagogue 13. Holocaust Memorial 14. Earl Bales Ski and Snowboard Centre 15. Earl Bales Community Centre (arrive 4:55pm) **Neighbourhoods** Lawrence Heights > Ledbury Park > Lawrence Manor > Armour Heights > Clanton Park **Map** [https://www.google.com/maps/d/edit?mid=1WRVGV7v8KyLlZf1cYDVL2KoWdwlrZds&usp=sharing](https://www.google.com/maps/d/edit?mid=1WRVGV7v8KyLlZf1cYDVL2KoWdwlrZds&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. Optional bagel tasting at the end of hike, outside Earl Bales Community Centre. * Blind tasting of sesame and/or poppy seed bagels from 6 bakeries. * Small portions. 1/8 to 1/16 of a bagel. * Rate them online. * $2. No refunds after orders are placed. Payment on the day of event by cash or e-transfer to globaltorontoeats@gmail.com. Exact change preferred. * Sign up for the bagel tasting at the start of the hike. If you're joining us after that, e-transfer before 2:30pm to guarantee food. **Limited cutlery and no plates provided**. Highly recommended to bring your own cutlery and containers for bringing back leftovers. See our [About section](https://www.meetup.com/hike-to-eat/) for more info.

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/)