Challenging Hikes Toronto

Midweek morning hike - Earl Bales

Challenging Hike at Hockley Hills and Mono Trail Loop

🍂 Crothers Woods Fall Hike & Ice Cream Treat! 🍦

## 🍂 **Crothers Woods Fall Hike & Ice Cream Treat!** 🍦 Toronto doesn’t have many true hiking trails — but Crothers Woods is one of the best! This beautiful wooded trail is especially stunning in the fall, with the leaves turning every shade of red and gold. We’ll start by walking along **Broadview Avenue to Pottery Road**, heading down the hill to meet the **Don Valley Trail**. From there, we’ll join the **Crothers Woods Trail**, take in the fall colours, stop for a short break, and then walk back. There are a few light hills — and one big one at the very end (Pottery Road, I’m looking at you!) — but don’t worry, there’s a sweet reward waiting. After all that hard work, we’ll stop for **Dairy Queen ice cream**! This hike is a bit more challenging than some of our regular walks, but totally worth it for the views (and the ice cream). **This event happens rain or shine!** *** ### 📍 **Meetup Details** **Meeting Spot:** Right outside **Broadview Subway Station** — I’ll be the one wearing the **Moose Hat!** 🦌 **Ending Spot:** Broadview Subway Station **Meetup Fee:** $5 (cash in person or e-transfer to **mathewmaclean@hotmail.com**) *** ### 🕒 **Timing** 11:00am and I will only wait 5mins — the hike should take about **2 hours**. You can leave anytime you like if you need to head back early. *** ### 🥾 **What to Bring** * Water * Good walking or hiking shoes * A snack * A positive attitude (and maybe room for ice cream!) ### *** ### ⚠️ **A Quick Note** Sometimes things come up and I might need to cancel or reschedule. Please keep an eye on the event page for updates. *** ### 👋 **About This Group** This group is open to **everyone** — whether you’re single or not, new to the city, or just looking to be social and make friends. We also host **movies, walks, hikes, arts & culture events, and restaurant outings**! You can RSVP ahead of time **or just show up** if you’re not sure you can make it — we’re flexible like that. *** **Organizer:** Mathew 📧 Email: **torontomoviesandoutings@hotmail.com** **Come for the trails.** **Stay for the conversation.** **Leave with a new connection — and maybe a new friend.** 🍂💛

🍁🎄 Niagara Falls Fall Hiking Trip & Festival of Lights! 🌈

# 🍁🎄 Niagara Falls Fall Hiking Trip & Winter Festival of Lights! 🌈 🌦️ **RAIN OR SHINE!** The adventure goes on, whether we're enjoying golden sunshine, crisp autumn air, or a little mist from the Falls. After a day of hiking, we'll finish with dinner and the spectacular Winter Festival of Lights! ✨ *** ## 🥾 About the Trip Let's escape the city for a full day of fresh air, friendship, and breathtaking scenery! We'll explore the natural side of Niagara Falls — less time in the tourist crowds, more trails, trees, and spectacular views. We'll meet outside the **Fairmont Royal York on Front Street West**, travel together by GO Train to Niagara Falls, and make our way to **Niagara Glen Nature Reserve** for a hike among ancient boulders, winding forest paths, and the turquoise waters of the Niagara River. The trail features stairs, uneven ground, elevation changes, and a climb back up out of the gorge. This is a proper hike, so please read the expectations below before signing up. *** ## 🌲 The Trail Experience Niagara Glen is a beautiful natural area carved into the Niagara Gorge over thousands of years. We'll follow forest trails, take photos, enjoy the fall colours, and experience a side of Niagara Falls that many visitors never see. The planned hike is approximately **4 km**, although the terrain makes it more demanding than the distance might suggest. We'll have opportunities to pause and enjoy the scenery, but everyone needs to be prepared for the physical demands of the route. ### ⚠️🥾 IMPORTANT: HIKE EXPECTATIONS — PLEASE READ CAREFULLY 🥾⚠️ **This is a real hiking trail, not a casual walk.** Before signing up, please be confident that you can: * ✔️ Walk for an extended period of time. * ✔️ Handle uneven terrain, stairs, elevation changes, and the climb back up out of the gorge. * ✔️ Keep up with the group at a steady pace without needing frequent or extended stops. * ✔️ Manage a full day of walking, travel, dinner, and evening sightseeing. **This is not the event to use to test your fitness level or see how things go.** If you're unsure whether you can complete the hike, please choose an easier event instead. If you find yourself unable to keep up, you may need to turn back or continue independently where the route and circumstances allow. The group cannot stop or slow down significantly to accommodate someone who is struggling, as this affects the experience and schedule for everyone. Please make an honest assessment of your abilities before committing. The goal is to keep the day safe, enjoyable, and on track for the entire group. *** ## 🍔 Dinner at Chuck's Roadhouse After the hike, we'll head to **Chuck's Roadhouse on Clifton Hill** for a relaxed dinner. Everyone is responsible for the cost of their own meal. ⚠️ **Please note:** The restaurant has limited vegetarian options. If this means you won't be joining us for dinner, please let me know in advance so I can plan the numbers. Please don't leave this until the last minute, as I'll be arranging the dinner headcount. *** ## 🎇 Winter Festival of Lights After dinner, we'll head down to the Falls to enjoy the **Niagara Falls Winter Festival of Lights**. The surrounding area comes alive with illuminated displays and colourful seasonal installations. We'll take a relaxed evening stroll, enjoy the atmosphere, and stop for photos along the way. Bring warm layers — temperatures near the Falls can drop, especially after dark! 🧣✨ *** ## 💲 Meetup Fee **$5 Meetup fee** 💵 Cash at the event, or 📧 E-transfer to **[mathewmaclean@hotmail.com](mailto:mathewmaclean@hotmail.com)** before or on the day. *** ## 🚆 TRANSPORTATION REQUIREMENT — PLEASE READ **Everyone must travel with the group on the GO Train to participate in this event.** We will not meet people separately in Niagara Falls. Travelling together helps us coordinate the day's activities, stay on schedule, and avoid confusion about meeting points and transportation. Please arrive on time at our Toronto meeting point. We will not be able to hold the train for late arrivals. *** ## 🕒 Travel Details (Approximate) * **8:15 AM** — Meet outside the main doors of the Fairmont Royal York on Front Street West. Look for my Moose Hat! 🫎 * **8:30 AM** — Depart for the GO Train. * **9:03 AM** — Planned GO Train departure for Niagara Falls. * **11:25 AM** — Expected arrival in Niagara Falls. * **12:30 PM** — Planned start of the Niagara Glen hike. * **4:30 PM** — Dinner at Chuck's Roadhouse. * **6:00 PM** — Head down to the Falls for the Winter Festival of Lights. * **8:00–9:00 PM** — Target return-train window to Toronto. 🚆 These times are approximate and depend on the transit schedule and conditions on the day. I'll share any necessary updates closer to the event. Please check the current GO Transit schedule before purchasing your ticket. *** ## 🎟️ Tickets & What to Bring Please purchase the **GO + WEGO Combo Ticket** in advance. The previously listed round-trip price was approximately $20, but please check the current price and service details before buying. 👉 **[Click here for the Niagara Parks GO + WEGO offer](https://www.gotransit.com/en/partners-and-promotions/go-train-to-niagara-on-weekends)** Bring: * 🥾 Sturdy walking shoes or hiking boots with good grip. * 💧 Water and snacks. * 🧥 Warm layers for the evening. * 📸 A camera or charged phone. * 🎒 Anything else you need for a full day outdoors. *** ## ⚠️ Important Notes * This is a full, active day involving a train journey, a hike, dinner, and evening sightseeing. * The event is open to everyone — singles, couples, and friends — provided they can manage the hike. * Please RSVP only if you understand the physical requirements and can commit to the day's itinerary. * You can RSVP ahead of time or show up on the day if you're unsure about your schedule, but please remember that the train arrangements and group itinerary require punctuality. * Sometimes things happen and I may need to cancel or change the plans. Please watch the event page for updates. *** 👤 **Organized by Mathew** Questions? Post on the event wall or email **[torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com)**. **Come for the hike.** **Stay for the lights.** **Leave with a full day of adventure and new connections.** 🍁🎄

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:* +0.5 liters *Extras:* Hiking pole (Highly recommended) *Required Gear:* Hiking boots or Trail Runners with good grip, Headlamp, and by December [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

Hike Leaders’ Meeting at Marjan’s Trail ✅

Our hike leaders are getting together to share ideas, plan future hikes and adventures and help our community continue to grow. Thank you to all our volunteers and members for making every hike a great experience. 🥾🥾

November Trek Alert | Desert Canyons & Epic Views

November Trek Alert | Desert Canyons & Epic Views Think: Red rock canyons Cool November weather Wide open trails Zero crowds, zero chaos We’ll be hiking Zion, Bryce Canyon, and the Grand Canyon at a comfortable, steady pace — with time to breathe, pause, and actually enjoy where we are. If you’ve been craving: ✔️ A reset ✔️ Nature over noise ✔️ Movement with meaning Motel 6 1322 Fremont Street, Las Vegas, 89101, United States

Exploring Mount Nemo

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/mt-nemo-fall-26)** **Mount Nemo is one of the best parts of the Niagara Escarpment and it's only a short drive from the city!** We'll follow the Bruce Trail for about 7 km along the top of the ridge, through old forest that grows right up to the cliff’s edge. Within a few minutes, while immersed in this UNESCO biosphere reserve, Toronto feels a lot further away than it is. This isn't a simple stroll but it is accessible for anybody wanting to get into hiking. The ground is broken up in the best way, with rock, roots and the odd scramble, and the route keeps changing character as we go. November is a good month to do it. The trail is quieter than in peak fall colour season, and depending on the year some leaves may still be hanging on. Most people arrive not knowing anyone, and by the time we're back at the cars you'll likely have a few new trail friends. **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 **Highlights** **Close to the City:** It's an hour drive from Toronto, which makes this one of the easiest ways to get onto the escarpment. **Views:** Whatever colour is left in the forest, set against the dark green of the cedars. Bare branches also mean longer sightlines across the valley. **Meet Your Crew:** A day on the trail with fellow members of the WU crew, and a few new people to plan the next hike with. **Itinerary** **10:00** \- Shuttle leaves from near Keele Station **10:00 - 11:00** \- Drive to trail head **11:00 - 15:30** \- Hike the trail with a stop for lunch along the way **15:30 - 16:30** \- Drive back to Toronto **Event cost: $55+HST. $40 optional transport also available. Please register [here.](https://www.wildernessunion.com/adventures/mt-nemo-fall-26)** **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/)***

Hiking at Rouge National Urban Park (Free OR $2)

Lets hike at Rouge National Urban Park. This is a popular hiking spot close to the city. Pls aim to arrive 12pm. We will wait 15 mins for people to show up and then start walking at 12:15pm. Washrooms may or may not be available. Pls stop at a McD or Tim Hortons before the hike if needed. **Meeting Spot** \- SEE BELOW COMMENTS **Transportation** No TTC access. You must drive/rideshare/carpool to reach the Meeting Spot. **Distance**: 6 to 9km (we will adjust the distance based on weather and how much energy we have that day). **Difficulty**: Moderate **Carpool**: Post in comments if offering/requesting carpool. **Event Fee\*** Free if you RSVP before Oct14 $2 if you RSVP on/after Oct15 **Cash** - *In person when you arrive at event* **Etransfer-** *[themoja@outlook.com](mailto:themoja@outlook.com) --> use password **meetup*** **Credit Card** - *[Pay via stripe online](https://buy.stripe.com/bJeeVd3li4Cq3rS7Gh0oM00)* 💬 **Stay Connected:** ***Join Whatsapp Group - [CLICK HERE](https://docs.google.com/forms/d/e/1FAIpQLSflzD3fDrU5sLARAT5yDF3OhEu3Vj-2P7ci8mP5FYX46rt1NQ/viewform)*** ***Follow on Instagram - [CLICK HERE](https://www.instagram.com/tam.club/)***

NEW TRAIL! 🍂 From Scarborough to North York: The Fall Colours Trail Walk 🌈

# 🍂 From Scarborough to North York: The Fall Colours Trail Walk 🌈 ### A Scenic Fall Adventure Through Trails, Ravines & Toronto History Toronto has some wonderful natural spaces tucked between its neighbourhoods, and this walk connects two of them into one longer adventure! We’ll begin in Scarborough, exploring the **Gatineau Corridor Trail**, with its wildflowers, tall grasses, and green spaces where nature is allowed to grow a little more freely. 🍁 From there, we’ll make our way along some city streets before connecting with another trail system and continuing through the surrounding ravines toward the **Rainbow Tunnel**. The tunnel is an unusual piece of Toronto history, painted in 1971 by teenager B.C. Johnson as a tribute to his friend Sigred, who died in a car accident. Although the artwork has seen better days, we’ll make a quick stop to see it before continuing toward our final destination. We’ll finish at **Shops at Don Mills**, where anyone who wants to can join us for coffee, a pastry, or something to eat after the walk. ☕🥐 This is a longer outing than some of our regular walks, but we’ll take our time, enjoy the scenery, and have a break along the way. *** ### 🚶‍♂️ What We’ll Do Along the route, we’ll: * Explore the Gatineau Corridor Trail and its naturalized green spaces 🌼 * Walk through parks and neighbourhood streets * Take a break midway through the walk * Connect with the Moccasin Trail and surrounding ravine paths 🌳 * Stop briefly at the Rainbow Tunnel 🌈 * Continue to Shops at Don Mills * Finish with an optional coffee or snack with the group ☕ The walk should take approximately **3 hours**, depending on the pace of the group and the conditions along the route. **Please note:** This is a point-to-point walk. We will not return to our starting location at Dollar Tree. At the end, I’ll help anyone who needs assistance figuring out their transit options. *** ### ☀️ Weather & Expectations This walk takes place in typical Toronto weather conditions. Please dress appropriately for the forecast and wear comfortable walking shoes. The route includes a mix of paved streets, trails, and potentially uneven or unpaved surfaces. There will be some distance to cover, so this walk is best suited to people who are comfortable walking for around three hours, with breaks. This is a social walk, not a race. We’ll keep a steady pace and make time to enjoy the surroundings. 🌦️ **This event happens rain or shine!** *** ### 🧢 Meetup Details 📍 **Starting Location:** Outside the Dollar Tree near Kennedy Station 🫎 **Look for me wearing my Moose Hat!** ⏰ **Meetup Time:** 11:00 AM I will only wait 5 minutes. **Early is on time. On time is late.** 🏁 **End Point:** Shops at Don Mills, North York 🚇 **Transit:** We’ll finish near the Eglinton line. I’ll help anyone who needs directions for getting home by transit. *** ### 🎟️ Meetup Fee **$5 cash in person or e-transfer to [mathewmaclean@hotmail.com](mailto:mathewmaclean@hotmail.com)** This fee helps support the group and allows us to continue organizing walks and other events throughout Toronto. *** ### ☕ After the Walk Once we reach Shops at Don Mills, anyone who wants to continue the outing can join us for coffee, pastries, or a bite to eat. It's a chance to relax, chat, and get to know one another after our walk. Participation is optional. *** ### 🎒 What to Bring 💧 Water 👟 Comfortable walking shoes 🥨 A snack 🧥 Weather-appropriate clothing 📱 Your phone or camera for photos *** ### 🌈 Who Is This For? This walk is great for: * People who enjoy discovering hidden parts of Toronto * Anyone interested in local history and unusual landmarks * Walkers who enjoy exploring trails and ravines * People looking to meet others and make friends * Anyone who wants to spend a few hours outdoors enjoying the fall colours The trails and Rainbow Tunnel are part of the adventure, but **the people you meet along the way are the real experience.** *** **REMEMBER:** You're welcome to RSVP ahead of time or just show up 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. 👤 **Organizer: Mathew** Questions? Post on the event wall or email **[torontomoviesandoutings@hotmail.com](mailto:torontomoviesandoutings@hotmail.com)** **Come for the trails.** **Stay for the conversation.** **Leave with a new connection — and maybe a new friend.** 🍂💛

Halloween Dance Party and Scavenger Hunt

**It's a Halloween Dance Party and Scavenger Hunt!** **Location: Party Room 51 Trolley Crescent** **(Scavenger Hunt is under the bridge)** **Non-refundable fee:** *****$20 by October 19th******** **$25 from October 20th to 28th **Send to** **boots4hikingthesix@gmail.com** **Party Details** ***Theme**: Unmask your hidden self.* *** Vibe*: Grown-up drinks, killer costumes, and zero filters. **Drop the mask and let your true monster out to play this Halloween.** Prize for best costume! Every day we wear the mask of the professional, the polite, and the responsible. Not tonight. This Halloween, it’s time to shed your civilized skin and unleash your **real personality**—no filters, no judgements, just pure, unadulterated fun. Come as who you *actually* are on the inside. 🖤 The Ritual *** Date: **Saturday, October 31st, 2026 *** Time: **7:00 PM until the spirits fade** *** Lair: We are just confirming the venue. We will keep you posted! 🍷 The Elements *** Potions & Brews: **Drinks and nibbles provided! *** Attire: **Costumes required. Dress as your inner alter-ego, your deepest obsession, or the version of you that only comes out after dark. *** The Vibe: **Dark beats, heavy pours, and wicked company. ADMISSION IS $20, Are you brave enough to show your true colours?

Bloor Street, Toronto. All of it. (19.6 km)

**Attendance policy is enforced for this hike**. See below for details. Back by popular demand, we're doing a mega hike along Bloor Street in Toronto. We'll trace the entire Bloor subway line and beyond. See how the landscape densifies from golf courses to strip malls to parks to gentrified neighbourhoods as we approach the Don Valley. The restaurants along the way highlight the cultural diversity of Toronto from 5 continents. You need to be in decent shape and have a voracious appetite to do the entire route. However, as with other hikes, you are free to join and leave at any point. Those who complete the entire route will be eligible to buy a commemorative T-shirt (expected price \~$23). There are several restaurants to choose from at the end of the hike: Japanese ramen, Mexican tortas, Egyptian koshari, and Brazilian steaks. Further on at Chester station are even more options: Iranian, Indonesian, and Greek grilled meats. We're not making reservations, so find a group of like-minded people and grab a table. For reference, here's a [map of all our past hikes](https://www.google.com/maps/d/edit?mid=1_FpYriQNv5okUB-oiCODi56uiRDgPGI&usp=sharing). We've covered a large chunk of Toronto and neighbouring cities. **Highlights** Segment 1: Markland Wood 1. Markland Wood Golf Club (depart 12:30pm) 2. Mississauga-Toronto border / Start (or end) of Bloor Street 3. Bloordale United Church 4. Matt's Burger Lab 5. Highway 427 6. Stari Grad / Zayzoun / Frenchie’s Doughnuts (depart 1:45pm) Segment 2: The Kingsway 1. Bonimi 2. Kingsway Fish & Chips 3. Old Mill 4. Chebureky House / Momo Ghar / Janchenko's Bakery (depart 3:05pm) Segment 3: Bloor West Village 1. The CakeSmith 2. Former Runnymede Theatre 3. Marvelous By Fred 4. Ohana 5. Andrea's Cookies 6. Thai Nyyom 7. 9 Mile Jamaican Cuisine / Momoheart / Chito's / Ruru Baked (depart 4:25pm) Segment 4: Bloorcourt Village 1. Bakerbots Baking 2. Komi Banh Mi Bar 3. Nosso Talho 4. Szechuan Noodle Bowl 5. Ambassador Pizza 6. Filosophy / Levant Pizza 7. La Bella Managua / Lalibela / Vit Beo 8. Christie Pits Park 9. PAT Central 10. Hodo Kwaja / Dessert Fox 11. Pizzeria Fornace / JJIN Toast 12. Eva's Original Chimneys / Cong Caphe (depart 5:45pm) Segment 5: Downtown 1. Souper Hot Pot / Myeongdong Gyoza Kalguksu 2. Trinity-St. Paul's United Church 3. Woojoo Bunsik / Zaad / The Daily Dumpling Wonton Co 4. University of Toronto 5. Koerner Hall / Royal Ontario Museum 6. Eataly 7. One Bloor 8. Yuzuki 9. The Manufacturers Life Insurance Company / Rogers HQ 10. Church of St. Peter and St. Simon 11. Prince Edward Viaduct 12. End (or start) of Bloor Street at Broadview Ave (arrive 6:55pm) **Neighbourhoods** Markland Wood > Bloordale Gardens > Eatonville > Islington - City Centre West > The Kingsway > Bloor West Village > High Park North > Junction Triangle > Bloordale Village > Bloorcourt Village > Christie Pits > Koreatown > The Annex > Yorkville > Upper Jarvis > St. James Town > Playter Estates **Map** [https://www.google.com/maps/d/edit?mid=1ESqH0dQk3idaJYpGztKGE8UVoR5wFX8&usp=sharing](https://www.google.com/maps/d/edit?mid=1ESqH0dQk3idaJYpGztKGE8UVoR5wFX8&usp=sharing) **How it works** Hike starts punctually. Late or can't join at the beginning? 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. The end of the hike is the only time when we can enjoy a leisurely meal. **Attendance policy** Please check in with an organizer when you arrive. 24 hours before the hike, we'll note down 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.