Challenging Hikes Toronto

Sunnybrook - Don River ADVANCED Hike 🌻

Good Luck Out Town Hike

Snow loops of Don Valley (8.1 km)

Golf courses are not just for golf. In winter, city-owned courses become cross-country skiing and snowshoeing territory. Of these, the Don Valley Golf Course has the largest and most scenic routes. It goes across rivers and under massive highways. Toronto's only ski lift is just outside its boundaries, which we can visit if the gate there is unlocked. After romping through the golf course, we'll continue exploration in the Hoggs Hollow neighbourhood. It has some historical buildings, a fancy French restaurant, and a 1850s tavern. Heading south along Yonge Street, we'll reach a clutch of eateries, where you can choose between Georgian, Indian, or Thai food. This event depends on snow. If there is heavy snowfall, you're encouraged to ski or snowshoe the golf course portion of the hike. If there is no snow and ice, we'll just walk. Walking in heavy snow is not recommended. If you must, wear muck boots and/or traction aids. After the golf course, the rest of the hike will be on foot. **Highlights** 1. Don Valley Golf Course main building (depart 12pm) 2. Golf turf blanketed in snow (or barren and grey) 3. Hogg's Hollow Bridge 4. Earl Bales ski lift 5. Don Valley Golf Course main building (depart 1:12pm) 6. Auberge du Pommier 7. C W Jeffrey's house 8. St. John's York Mills Anglican Church 9. York Mills Centre (depart 1:40pm) 10. Miller Tavern 11. Tamada Georgian Restaurant / Mumbaikar 12. Pii Nong Thai (arrive 2:05pm) **Neighbourhoods** Armour Heights > Hoggs Hollow > Bedford Park **Map** [https://www.google.com/maps/d/edit?mid=1clcrZAR9LCTyev1-8BHf3pNAgyS-Muw&usp=sharing](https://www.google.com/maps/d/edit?mid=1clcrZAR9LCTyev1-8BHf3pNAgyS-Muw&usp=sharing) Moderate incline going down from golf course, potentially covered in ice. Stairs to St John's York Mills Anglican Church. Uphill along Yonge St from York Mills to Glen Echo. Free admission to golf course in winter. **How it works** Hike starts punctually. Late or can't do the whole route? Meet us at scheduled checkpoints. See our [About section](https://www.meetup.com/hike-to-eat/) for more info.

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

🌳🦆⛵ URBAN WALK: High Park to Harbourfront (10 Km): SAT, Feb 21

We will take a leisurely walk from Bloor West and High Park Ave. to **Harbourfront,** via **High Park,** **Sunnyside Park** and the Toronto **Waterfront Trail.** Join this outdoor event to behold some amazing views of High Park, **Lake Ontario,** the Toronto skyline, Canadian geese, ducks and other wild animals. **All walking/ hiking levels welcome**. We will take breaks along the way for beverages and/or washroom needs. **Length:** 10 Km. This is a LINEAR hike, but the end point is WELL CONNECTED to both **Line 1** (Yonge-University) and **Line 2** (Bloor-Danforth). You may return to either Subway line by TTC streetcar. * DIFFICULTY LEVEL: Beginner -- all levels welcome! * WHAT TO BRING: Water (at least 1 L), hiking shoes/ boots and cash for TTC fare and personal purchases. * POST-EVENT: Refreshments at a cosy restaurant at Harbourfront, OPTIONAL (around 4:30 PM) **Event conditional on weather.** In the event of harsh weather, this walk will be cancelled or rescheduled. **\*\*\* PLEASE, BE ON TIME \*\*\*** We will not wait for anyone after 1:15 PM. It is not okay to join the event or call the Organizer after the event starts at 1:15 PM. ⭐️ **Event Fee:** $5/ person (only $4 if paid ONLINE) ⭐️⭐️ HOW TO PAY ⭐️⭐️ You may pay the **$5** fee CASH at the beginning of the event, or online via Interac **E-Transfer** (Save $1). * Send payment to: **Walter De Marco** * Email: **thats.walter@yahoo .com** * E-Transfer security question: What is this payment for? * Answer: **"Adventure"** * * GETTING THERE **Bloor St. West and High Park Ave,** Toronto ⭐️ **[Google Map](https://goo.gl/maps/7jd6deCtdU5PdAhx6)** ⭐️ **[>> Click HERE <<](https://goo.gl/maps/7jd6deCtdU5PdAhx6)** * * **TTC Directions:** Take the Subway to High Park Stn and walk East on Bloor St to High Park Ave. * **By Car:** This is NOT a loop walk, so if you leave your car at the starting point, you will have to walk or take public transit back to your car. The best thing to do is leave your car at a TTC Subway Stn., and then return to your car by TTC. There are streetcars that connect Harbourfront to both the Yonge and the Bloor Subway line. ===================================== * DISCLAIMER During all events, members are responsible for themselves. All events in this Meetup group are planned and operated by organizers with several years of experience as hike leaders. However, we make no claims of being professional guides, and take no responsibility for the outcome of any of our trips or activities.

Urban Walk: Introductory Hike – Crothers Woods

Anyone is welcome to join this hike but we are especially inviting our new members (and prospective members) to learn about our hiking program and how our guided hikes are classified and described in the hike schedule and what you should bring with you on hike. We will explore Crothers Woods in the Don Valley, nature in the heart of the city, which will present some moderate challanges with it's ups and downs giving it's Level 2 classification. The actual route will depend on conditions of the day to keep it a moderate level hike. Please bring ice traction cleats (mandatory) for a safe hike. We'll have a brief outdoor snack/lunch stop along the route. We will return to Todmorden Mills at the end of the hike. Note transit users will need to ascend the fairly steep hill on Pottery Road at the conclusion of the hike. Washrooms are available at the Todmorden Mills Site. On this introductory hike we will: * Discuss how a hike is classified (Level 1,2,3, Moderate/Fast, etc) * Discuss the variables that affect the difficulty of any particular hike * Discuss why different people have different perspectives on the difficulty level of the same hike * Demonstrate some terrain that would raise the difficulty level of hike hiking * Help you know you have the information required to choose the hikes right for you Register At BTC website : [https://hikes.brucetrail.org/event/crothers-woods-introductory-hike/2026-02-22/](https://hikes.brucetrail.org/event/crothers-woods-introductory-hike/2026-02-22/) Please register at above so we have you on the waiver form

❄️ Winter Ravines Walk: Finch West to Downsview Park ❄️

**❄️ Winter Ravines Walk: Finch West to Downsview Park ❄️** If winter has been making you want to hibernate, this is your sign to bundle up, step outside, and do something that feels genuinely good for the soul. This winter walk is all about fresh air, movement, conversation, and discovering just how much green space is quietly tucked into the city — even in the colder months. We’ll start at **Finch West Subway Station** and head out together along the **Finch Corridor Trail**, an unexpectedly peaceful stretch that eases you into the walk. From there, we’ll move through **Derrydowns Park** and **Downsview Dells Park**, where winter turns the ravines into a calm, almost meditative landscape — snow-dusted paths, bare trees, and that crisp, quiet feeling you only get this time of year. This isn’t a power walk and it’s not a hike that leaves you gasping for air. It’s an **easy-to-moderate winter stroll**, paced so people can chat, get to know one another, and actually enjoy where they are. These walks have a way of breaking down walls — conversations flow more easily when you’re walking side by side, and by the time we reach the end, strangers often feel like familiar faces. We’ll finish our journey at **Downsview Park**, wrapping up at **Downsview Park Subway Station**, feeling refreshed, accomplished, and very glad we didn’t stay inside. 📱 **Don’t forget to join our WhatsApp group** – [CLICK HERE!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc?mode=ac_t) \*\*\* \#\#\# ❄️ Meetup Details ❄️ ⚠️ **Please Note:** This is a true winter walk. Don’t sign up if you’re not comfortable walking in cold or snowy conditions. ✔️ The walk happens in *almost* all weather ❌ The event will be cancelled only if it’s **-20°C or colder** 📍 **Meetup Location:** Outside **Finich West Subway Station** — look for Mathew in his iconic **Moose Hat** 🫎 ⏰ **Meetup Time:** **11:00 AM** — I will only wait **5 minutes** (this is a firm 5 minutes because… winter ❄️😉) 💲 **Meetup Fee:** $5 cash in person **or** e-transfer to \*\*[mathewmaclean@hotmail.com**](http://mathewmaclean@hotmail.com%2A%2A/) 🏁 **End Spot:** Yorkdale Mall \*\*\* \#\#\# 🧣 What to Bring 🧣 • Water • Good winter boots • Gloves & hat • Something warm to drink ☕ • A small snack • A friend, family member or guest \*\*\* 🚶‍♂️ **Can I Leave Early?** Absolutely — leave anytime you like. This walk may take up two hours. \*\*\* 💛 **REMEMBER:** You can just show up — or decide on the day if you’re not 100% sure. ⚠️ **NOTE:** Sometimes things happen and plans may change — please keep an eye out for updates. \*\*\* 👤 **Organizer:** Mathew Questions? Post on the event wall or email \*\*[torontomoviesandoutings@hotmail.com**](http://torontomoviesandoutings@hotmail.com%2A%2A/)

Little Somewhat Italy and Portugal (5.8 km)

Little Italy and the neighbouring neighbourhood, Little Portugal, are enclaves for the first Italian and Portuguese settlers in Toronto. Today, these neighbourhoods are less distinctly Italian/Portuguese. They have become trendy districts for global food. In fact, they boast the highest density of top-rated restaurants in Toronto. There are some attractions along the way like murals, an Italian broadcaster, and a Portuguese parkette. But the highlight is undoubtedly the profusion of restaurants, bars, and nightclubs. We'll take a quick detour to Trinity-Bellwoods park before ending at a northern Italian restaurant featuring Lombardy cuisine. No pizzas, just steak, breaded cutlets, and other rich foods. **Highlights** 1. Dundas St W and Bathurst St southeast corner (depart 6:30pm) 2. Garage door murals at Boxcar Social Laneway 3. Bar Raval 4. Liu Loqum Atelier 5. Italian Walk of Fame / PG Clucks 6. Portuguese Walk of Fame 7. Casa Tropical / The Daily Dumpling Wonton Co 8. Mayil Coffee 9. West End YMCA 10. Gateau Ghost 11. Death In Venice 12. Youngplace 13. Trinity Community Recreation Centre (depart 7:55pm) 14. Harry and Heels California Donuts 15. Stelvio (arrive 8:20pm) **Neighbourhoods** Little Italy > Trinity-Bellwoods > Little Portugal **Map** [https://www.google.com/maps/d/edit?mid=1ZMfY8WowqpbeBxg91X-NsNTDtv6HGWc&usp=sharing](https://www.google.com/maps/d/edit?mid=1ZMfY8WowqpbeBxg91X-NsNTDtv6HGWc&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. Grab ready-made food, or 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.

Frozen Rapids Snowshoe

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/historic-winter-2026)** ***Join us as we explore this seemingly untouched wilderness known to just a few.*** This hike is a genuine adventure, taking us to a spot where trails appear out of nowhere then disappear again as soon as you find them. While only 9km, this is a harder hike that will see us bushwhacking through dense forest, hopping over myriad streams and potentially trudging through thick snow. The reward is incredible however - we end up tracing a raging river along an impossibly pretty shoreline and past some ferocious rapids. If you've been itching for something a bit more challenging, this is your chance. On this hike you can expect: \- Trekking along icy rivers \- Sprawling frozen scenery \- Raging rapids \- An epic feat of engineering ***A note for self-drivers: parking can be precarious here, especially with heavy snowfall. You are strongly encouraged to take WU transport to avoid issues.*** ***Snowshoes are included in the cost of this adventure. Please indicate at checkout if you require a pair.*** **Highlights** **Ferocious Rapids -** Trek along this winding riverbank with tumultuous rapids forming the river's path **A Forgotten River -** This river is teeming with life and beauty, how could anyone forget that! **Little-Known Crown Land Hike -** Hike through the unknown where the trail comes and goes. We doubt you'll see anybody else out there. **Event cost: $60+HST - optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/historic-winter-2026)** **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/)***

VMC and the real Little Italy (8.2 km)

Italian immigrants have long moved out of Little Italy in downtown Toronto. Find them in Vaughan, home to a plethora of Italian restaurants, booming condos, and the local mafia. The areas around Vaughan Metropolitan Centre (VMC) and Highway 7 / Weston Rd are packed with industrial food outlets. We'll visit two cheese superstores, a seafood mart, and other hidden gems. It's not just Italian food either. There's Vietnamese and a growing Turkish presence. Also, one of the top 3 croissants in the GTA. And a winery tour (subject to availability). If that's not enough Mediterranean food for you, stay for a meal at a upscale Greek restaurant or grab Roman pizza and panini at a hidden takeout joint. **Highlights** 1. VMC (Vaughan Metropolitan Centre) Library (depart 12pm) 2. Mapletri Supermarket 3. Bartholomew Bakery 4. Ricci's Pizzeria (depart 1:10pm) 5. San Antonio Seafood Market / Grande Cheese 6. Ciao Roma / Nes Bakery 7. Quality Cheese 8. Magnotta (depart 2:25pm) 9. Zet's Restaurant 10. Nonna Amina Turkish Bakery 11. Gulbay Turkish Bakery 12. Medusa Authentic Greek Cuisine / Giro Bottega / Corned Beef House (arrive 3:25pm) **Neighbourhoods** Vaughan Metropolitan Centre > Vaughan Business Park > Woodbridge **Map** [https://www.google.com/maps/d/edit?mid=15a06BMqNFARkynRVVr-2Fn3-1ow7Wag&usp=sharing](https://www.google.com/maps/d/edit?mid=15a06BMqNFARkynRVVr-2Fn3-1ow7Wag&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. Grab ready-made food, or 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. 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.

❄️🌲 High Park Winter Wander + Cozy Lunch 🍲✨

March in Toronto is a mystery… it could be sunshine and birds chirping ☀️ or a little crisp and snowy ❄️ — and honestly? That’s part of the adventure. Let’s get out of the house, breathe in that fresh winter air, stretch our legs, and enjoy one of Toronto’s most beautiful parks together. 💙 **High Park** is the city’s largest public park — full of winding trails, little hills (yes, there are a few! 😄), open green space, squirrels plotting world domination 🐿️, a mini zoo, lakefront views, and some of the prettiest natural scenery in the city. This isn’t a power hike. This isn’t a marathon. This is a **fun, light, social winter wander** — about an hour of walking, chatting, laughing, and just being outside together. 🌬️👟 And then? We warm up at the **Grenadier Café**, right in the heart of the park, for a cozy lunch. ☕🍔🍟 Nothing hits quite like a warm meal after a brisk walk. Fresh air + good conversation + comfort food. That’s the vibe. ✨ *** 📱 **Don’t forget to join our WhatsApp group** – [CLICK HERE!](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc?mode=ac_t) 👉 **Menu:** [Click Here!](https://www.grenadiercafe.net/grenadiercafemenu) *** ## 📍 Meetup Details 📌 **Meetup Location:** At the **High Park Sign** (west side at Bloor & High Park Ave). Look for Mathew in his famous **Moose Hat!** 🫎🎩 🕚 **Meetup Time:** 11:00 AM I will only wait 5 minutes (March weather waits for no one 😉). 📍 **End Location:** Back to the start. 💰 **Meetup Fee:** $5 cash in person or e-transfer to **mathewmaclean@hotmail.com** *** ## ❄️ Weather Policy Please don’t sign up if you’re not ready to walk in the cold or snow. This event is happening in *any* kind of weather — unless it hits -20°C. Then we call it character-building and reschedule. 😅 *** ## 🎒 What to Bring 🥾 Good boots (High Park has hills!) 🧤 Gloves & hat 💧 Water ☕ Something warm to drink 🍫 A small snack if needed *** ## ⏳ Can I Leave Early? Of course! Stay for the walk, stay for lunch, or stay for both. Come for as long (or as little) as you like. And yes — you can just show up on the day if you’re not 100% sure you can make it. ⚠️ Occasionally things happen and events may need to be cancelled — please keep an eye out for updates. *** 👤 **Organizer:** Mathew Questions? Post on the event wall or email **torontomoviesandoutings@hotmail.com** *** Let’s shake off winter blues, get some fresh air in our lungs, and remind ourselves how good it feels to move, connect, and share a meal together. 🌲❄️💛 High Park in winter has its own kind of magic — come see it with us.

🚶‍♀️Family Day Hike: Humber River Trail 🥾