Challenging Hikes Toronto

Earl Bales Park Mountain Goat 🐐 - Challenging Hike ⛰️ ⛰️

Sunnybrook - Don River ADVANCED Hike 🌻

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: Secret Wilderness Hike & Swim

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/ragged-rapids)** ***The Wilder Series is back! Are you up to the challenge?!*** We're heading deep into Ontario's Canadian Shield for a day on one of the province's most rugged backcountry routes. Tucked inside a little-known nature location, this trail trades manicured paths for raw granite, beaver dams, and dense forest that test both legs and navigation skills in equal measure. While only 15km, this trek and it's technical terrain are no joke. However, the payoff is incredible: raging rapids, amazing views and an incredible wilderness swim that you won't soon forget! **Secret Location** This is one of Wilderness Union's secret hikes. We visit spots that are undiscovered by the wider world, keep them pristine, and share them only among members. The location is revealed to registered members in the days before the trip. ***Please note that attendees will need a high fitness level to successfully complete this adventure. This will be a serious challenge!*** **Highlights** **True Wilderness:** Experience the Canadian shield in all of its glory! Unmanicured, untamed and unbelievably beautiful. **Beaver Dams:** Cross quiet backcountry ponds and streams along the way. **Powerful Rapids**: The Black River churns through a gorge with 20–30m cliffs. **Event cost: $60+HST (for explorer members) - $50 optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/ragged-rapids)** **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/)***

Double Donaconda, Crothers Woods & Todmorden Dirt Hill - 10+KM ADVANCED Hike

Come to BC With Us!

Holiday Time! I'm away for a week. Keep an eye on the schedule for our sunday hikes!

Train & Barenaked Ladies with Matt Nathanson

🌳🌊 HIGH PARK TO OLD MILL ADVENTURE - Stop at Tom's Dairy Freeze - 12KM🍦🚶‍♂️

# 🌳🌊 HIGH PARK TO OLD MILL ADVENTURE (12KM) 🍦🚶‍♂️ **Parks, Waterfront Views, the Humber River & One of Toronto's Best Ice Cream Stops** If you're looking for a walk that showcases some of the very best of Toronto, this is it. Join us for an incredible 12 km adventure that combines everything that makes Toronto special—beautiful parks, scenic waterfront trails, the Humber River, hidden nature, and, of course... ice cream! We'll begin in the heart of High Park before making our way through the park's winding trails and towering trees. From there we'll head down to the Sunnyside Boardwalk, enjoying stunning views of Lake Ontario as we stroll along the waterfront. After a relaxing shortt break, we'll continue north along the Humber River Trail before rewarding ourselves with a stop at the legendary **Tom's Dairy Freeze**, a Toronto institution that's been serving some of the city's favourite soft serve, burgers, and fries since 1969. Our adventure finishes at Old Mill Subway Station after experiencing four completely different sides of Toronto—all in one walk. 📲 **Join Our WhatsApp Group:**[ Click here to join](https://chat.whatsapp.com/DRFTkxRlHS4B3IL1lMleUd) *** ## 🧢 Meetup Details 📍 **Meetup Location:** High Park Sign (west side of Bloor Street & High Park Avenue) 🫎 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. Please be on time as we will leave promptly. 🏁 **End Point:** Old Mill Subway Station *(Please note this is a one-way walk. We will not return to High Park.)* *** ## 🍦 Our Ice Cream Stop We'll stop at **Tom's Dairy Freeze**, a beloved Toronto landmark that has been serving delicious soft serve, burgers, fries, and frozen treats since **1969**. Whether you choose a classic cone, sundae, or milkshake, it's the perfect reward after a day of walking. **Click Here to Learn More!** *** ## 🚶‍♂️ What We'll Do Our route includes: 🌳 Exploring High Park 🌊 Walking the Sunnyside Boardwalk 🌿 Following the Humber River Trail ☀️ Taking a relaxing short break along the way 🍦 Stopping at Tom's Dairy Freeze for ice cream -**BRING CASH!** 🚇 Finishing at Old Mill Subway Station This is approximately a **12 km walk** and takes around **4 hours**, including our break. *** ## ☀️ Weather & Expectations This walk happens rain or shine unless severe weather makes it unsafe. Although this isn't a difficult hike, it **is a longer walk**, and participants should be comfortable walking 12 km at a steady social pace. There are also **several sets of stairs near the end** of the walk, so please be prepared for a final climb before reaching Old Mill Station. This is a social walk—not a guided historical tour. The goal is to enjoy the outdoors, explore the city, and spend time getting to know one another. ## 🎟️ 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 organizing events like this. Thank you for supporting community! 💖 *** ## 🎒 What to Bring 💧 Water 👟 Comfortable walking shoes 🥨 A snack 🍦 Spending money if you'd like ice cream - **BRING CASH!** ☀️ Sunscreen on warmer days *** ## 🌈 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. Sometimes things happen and events may need to be cancelled—please keep an eye on updates. To help us plan our events, members who repeatedly RSVP and then cancel at the last minute may be removed from the group. *** 👤 **Organizer:** Mathew Questions? Post on the event wall or email: 📧 **[torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com)** **Come for the park.** **Stay for the waterfront.** **Leave with tired legs, new friends, and an ice cream in your hand.** 🌳🌊🍦

🌿🚶‍♂️ NEW TRAIL! EAST DON TRAIL ADVENTURE 🍪🥾

# 🌿🚶‍♂️ NEW! EAST DON TRAIL ADVENTURE 🍪🥾 **Toronto's Newest Ravine Trail, Riverside Views & Fresh-Baked Cookies** Have you walked Toronto's newest trail yet? Join us as we explore the recently completed **East Don Trail**—one of the city's newest and most exciting additions to Toronto's incredible ravine system. Connecting communities that were once separated, this beautiful trail follows the East Don River through peaceful forests, wetlands, and scenic valley landscapes that many Torontonians have never experienced. If you've done the Lower Don Trail, this is a completely different experience. Think quieter trails, beautiful river views, brand-new pathways, and the feeling of discovering somewhere new. Most of the route is paved and easy to walk, making it perfect for a relaxed day outdoors. Just one warning... what goes down must come up! 😄 The final section includes one fairly steep hill, so while the walk is suitable for most people, you should be comfortable tackling a good climb at the end. After the walk, we'll reward ourselves with a stop at **Peak Freans Cookie Outlet**, where you can stock up on discounted cookies and treats. Those who would like to continue are welcome to join us afterward for lunch at **Swiss Chalet**. 📲 **Join Our WhatsApp Group:**[ Click here to join](https://chat.whatsapp.com/DRFTkxRlHS4B3IL1lMleUd) *** ## 🚶‍♂️ What We'll Do We'll begin at Broadview Station before making our way into the Don Valley to explore Toronto's newest trail. Along the way we'll: 🌿 Walk beside the East Don River 🌉 Cross new bridges and pathways 📸 Enjoy beautiful ravine scenery 🍪 Stop at the Peak Freans Cookie Outlet 🍽️ Finish with an optional lunch at Swiss Chalet 🚌 Return to **Coxwell Subway Station** by TTC bus. Please note that **this is a one-way walk**. We will **not** return to Broadview Station. *** ## ☀️ Weather & Expectations This walk happens rain or shine unless severe weather makes it unsafe. The trail is mostly paved and relatively easy, but there is one fairly steep hill near the end of the walk. Please come prepared for that final climb. This is a social walk, not a guided historical tour. We'll enjoy the scenery, conversation, and the chance to explore one of Toronto's newest green spaces together. *** ## 🧢 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. Please be on time as we will leave promptly. 🏁 **End Point:** Coxwell Subway Station (via TTC bus). *** ## 🍪 After the Walk We'll stop at the **Peak Freans Cookie Outlet**, where you can browse their famous selection of cookies, crackers, and treats at outlet prices. Afterward, anyone who would like to continue is welcome to join us for lunch at **Swiss Chalet**. *** ## 🎟️ 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 organizing events like this. Thank you for supporting community! 💖 *** ## 🎒 What to Bring 💧 Water 👟 Comfortable walking shoes 🍪 Spending money if you'd like cookies 🍽️ Money if you'd like to join us for lunch *** ## 🌈 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. Sometimes things happen and events may need to be cancelled—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 Toronto's newest trail.** **Stay for the cookies.** **Leave having discovered another hidden corner of the city's incredible ravine system.** 🌿🍪✨

Crothers Woods in Don River Valley. Moderate. 2.7

🌅 Tommy Thompson Sunset Walk & Lighthouse — Wildlife & Skyline (9km)

🌿🌳 SUMMER EVENING WALK: GUS HARRIS TRAIL 🌳🌿

# 🌿🌳 SUMMER EVENING WALK: GUS HARRIS TRAIL 🌳🌿 **A Hidden Ravine, Easy Walking & Great Conversation** Sometimes the best parts of Toronto are the ones most people drive right past. Join us for a relaxed summer evening walk along the Gus Harris Trail, one of Toronto's hidden ravine trails that follows the peaceful Taylor-Massey Creek through Scarborough and East York. This isn't a challenging hike—it's an easy, mostly flat walk that's perfect for anyone looking to enjoy nature, get some fresh air, and spend an evening with great people. The real purpose of the walk isn't simply reaching the end of the trail. It's creating the space to slow down, have conversations, meet new people, and enjoy a few hours away from the busyness of everyday life. Along the way we'll follow the creek, enjoy the shade of the ravine, and discover one of Toronto's quieter green spaces that many people never even realize exists. ✨ **Fun Fact:** Taylor-Massey Creek is named after two prominent Toronto families. The Taylor family owned the famous Don Valley Brick Works, now known as Evergreen Brick Works—one of Toronto's most successful environmental revitalization projects. 📲 **Join Our WhatsApp Group:**[ Click here to join](https://chat.whatsapp.com/DRFTkxRlHS4B3IL1lMleUd) *** ## 🚶‍♂️ What We'll Do We'll spend about two hours enjoying an easy walk along the trail, taking our time, chatting, and getting to know one another. This is a social walk—not a race. There are very few hills, making it a comfortable walk for most people with a reasonable level of fitness. We'll finish back where we started before the park closes for the evening. *** ## ☀️ Weather & Expectations This walk will happen rain or shine unless severe weather makes it unsafe. Please wear comfortable walking shoes and dress appropriately for the weather. The focus isn't covering as much ground as possible. The focus is spending a relaxing evening outdoors with good company. *** ## 🧢 Meetup Details 📍 **Meetup Location:** Outside Victoria Park Subway Station by Victoria Park road. 🫎 I'll be wearing my Moose Hat. ⏰ **Meetup Time:** **6:00 PM** I will only wait **5 minutes.** Early is on time. On time is late. 🏁 **End Spot:** Victoria Park Subway Station (before the cemetery gates close). *** ## 🎟️ 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 organizing events like this. Thank you for supporting community! 💖 *** ## 🎒 What to Bring 💧 Water 👟 Comfortable walking shoes 🥨 A snack (optional) 🌞 Bug spray or sunscreen if needed *** ## 🌈 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. Sometimes things happen and events may need to be cancelled—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 conversation.** **Leave having discovered that sometimes** **Toronto's best hidden places aren't the destination—they're simply where new friendships begin.**