Challenging Hikes Toronto

Midweek morning hike - Earl Bales

1'st Fall Hike

This is a strenuous hikes consisting of three trails with very short steep sections and with elevation gains but you will be rewarded with lookouts and panoramic views. A very short section consists of brushing up against some tall grasses: there are caution signs on all the designated trails for ticks, so dress appropriately. And you already know to bring snack & water. Walking sticks may prove a hindrance. Location: Rouge Park (near the zoo) #of hikers: 7 + 1 Distance: 7 km (approx.) Duration: 3 hrs Parking: available I will post meeting place at a later date. Thanks Chris

Utah Hiking Trip

Hike in monument valley and visit archesnational park for a moderate hike

Early Morning Hike at the Lake!!! 🌞Scarborough lakeshore. 🌊 🦢

Cliffs & Fall Colours: A Bruce Peninsula Hike

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/bruce-peninsula-26)** **The Bruce Peninsula does dramatic better than almost anywhere else in Ontario, and fall is when it really shows off.** We'll be out for most of the day, covering 8.5km of moderate hiking through some of the best autumn scenery in the province, with the changing leaves against the escarpment's limestone making for a proper contrast. We'll start in the forest before the trail opens onto the coastline, tracing the cliffs down to the Grotto. It's the most photographed spot on the peninsula for good reason: crystal clear water, a sea cave carved into the rock, and a natural window out to the bay. We'll take our time here, including a stop for lunch. From the Grotto we'll keep following the shoreline out to Stormhaven, crossing pebble beaches with open views across Georgian Bay the whole way. We'll turn around there and retrace the coastline back, catching all the same cliffs and colour from the other direction with the light shifted by then. **Two important things to note:** 1. **Self driving isn't possible for this trip. Parking passes at the trailhead sell out well in advance, so all members travel together on WU transport.** 2. **Bruce Peninsula National Park is stunning, but be aware that it is a long drive there and back. Full details are in the itinerary below.** **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** **The Grotto:** The peninsula's most famous natural feature: a limestone sea cave with turquoise water and a rock window looking out over Georgian Bay. **Stormhaven Coastline:** A stretch of cobble beach with wide open views across the bay, well past where most day hikers turn around. **Fall Colour on the Escarpment:** Peak autumn colour against the Niagara Escarpment's pale limestone cliffs, a contrast you don't get anywhere else on the Bruce Trail\*\*.\*\* **Event cost: $140+HST. Transportation is included in the cost of the adventure. Please register [here.](https://www.wildernessunion.com/adventures/bruce-peninsula-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/)***

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 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

Wilket Creek, Serena Grundy, Sunnybrook, Edwards Garden AND Stretching!

**MeetUp Point: James for Entrance is off Leslie Street. Turn left on Leslie to Parking Lot 2 in Wilkett Creek Park** (Don't follow the pin!) **Join James for a 12 km hike that is challenging!** Starting past Wilcott Parking Lot 2, we will be passing through a number of parks and hills. For lunch we can stop at the TBG Bloom cafe for lunch or coffee ---- you might need one; or bring your own lunch. We will finish the hike with much needed yoga streches. It might be muddy, so ensure you have proper footwear! Also layers please, as we are heading into cooler weather!

🏕️ 3 Days, 6 Spots: Algonquin Park Awaits

Get your boots ready—we’re heading into the heart of [Algonquin Provincial Park](https://www.ontarioparks.ca/park/algonquin) for a 3-day backcountry hiking extravaganza. Expect stunning views, crisp forest air, brilliant colors and three full days of asking each other, *"Does anyone know which way is North?"* **The Catch:** * **Cap:** Strictly limited to **6 hikers** (because 7 is a crowd, and 8 requires a larger campfire circle). No camping just glamping in a hotel. * **Duration:** 3 days of pure trail bliss. * **Date:** October 16-18. That’s Friday to Sunday * **Details:** Top secret for now. Trail maps, packing lists, and more will drop as soon as you lock in your spot. First 6 to RSVP by September 14th get a ticket to the trail. Hit reply to claim your spot before the bears beat you to it on this luxury autumn trek 🌲🥾 🍂

Life of Fife (6.4 km)

The Bridle Path is famous for being the richest address in Toronto. Most people don't realize that the neighbourhood just to the north is equally affluent. Fife Road and Fifeshire Road are lined with swanky mansions, one of which was featured in a highly successful Canadian comedy. This hike is an opportunity to gawk at luxury homes before we exit into the lush foliage of Windfields Park. The park is also home to the bucolic Canadian Film Centre. Unfortunately, rich neighbourhoods don't have good restaurants. There's only one decent one, a Cantonese restaurant, where we can have dinner. **Highlights** 1. York Mills Arena (depart 6:15 pm) 2. Mansions of Fifeshire Rd 3. St. Andrews Park 4. York Mills and Bayview Ave (depart 6:55 pm) 5. Canadian Film Centre 6. Windfields Park 7. Banbury Community Centre (depart 7:30 pm) 8. Pearl Chinese Cuisine (arrive 7:55 pm) **Neighbourhoods** St Andrews > Windfields **Map** [https://www.google.com/maps/d/edit?mid=1LX-fTnFET4MwGjl5zzE6CG1epvLdcTM&usp=sharing](https://www.google.com/maps/d/edit?mid=1LX-fTnFET4MwGjl5zzE6CG1epvLdcTM&usp=sharing) **How it works** Hike starts punctually. Late or can't do the whole route? Meet us at scheduled checkpoints. See our [home page](https://www.meetup.com/hike-to-eat/) for more info.

Humber Bay Shores Farmers Market and High Park Ravines (11.3 km)

Join us on this hike to Humber Bay Shores Farmers Market, taking place in the picturesque Humber Bay Park West. It's the final one of the season. You'll find an incredible variety of farm-fresh produce, baked goods, artisanal products, preserves, meats, and more, all sourced from the city and surrounding regions. The market is a staple of the community, fostering engagement and supporting local agriculture. After the market, we will head east over the Humber Bay Arch Bridge to High Park and through its ravines, ending at Keele Station. Those who want a sit-down meal can continue east on Bloor St for Ukrainian syrnyky (cheese pancakes), deruny (potato pancakes), green borscht, and varenyky (dumplings). **Highlights** 1. Old Mill subway station (depart 10:30am) 2. Old Mill 3. Humber River Recreational Trail 4. Oculus Pavilion 5. Floating bridge over Humber Bay wetlands 6. Humber Bay Shores Farmers' Market 7. Views of CN Tower and downtown Toronto 8. Humber Bay Arch Bridge 9. Grenadier Pond 10. Spring Creek 11. Bloor and Keele (arrive 1:45pm) **Neighbourhoods** The Kingsway > Sunnylea > Stonegate-Queensway > Humber Bay Shores > Sunnyside > High Park **Map** [https://www.google.com/maps/d/edit?mid=12q2PqID-bXHnS1prfD9QVvxdc3tWhTE&usp=sharing](https://www.google.com/maps/d/edit?mid=12q2PqID-bXHnS1prfD9QVvxdc3tWhTE&usp=sharing) Unpaved and narrow trails in High Park. **How it works** There are no scheduled checkpoints for this hike. If late, you can try to find us at the farmers market. Bus 66B goes to the market from Old Mill Station. See our [homepage](https://www.meetup.com/hike-to-eat/) for more info.

Fall Walk: Finch Recreational Trail & Park Adventure! 🌾🚶‍♂️ (16KM)

# 🍁 Fall Walk: Finch Recreational Trail & Park Adventure! 🌾 ### An Easy, Flat Fall Walk Through Toronto's Green Spaces Looking for an easy way to enjoy the fall colours without tackling a difficult hike? Join us for a relaxed walk from **Pioneer Village Station to Finch Station**, travelling through Black Creek Parkland and along the **Finch Recreational Trail**. This is one of our members' favourite walks for a reason. The route is mostly flat and takes us through open fields, wooded areas, and quiet green spaces that feel surprisingly far removed from the city. We'll take our time, enjoy the changing leaves, stop for a break by **Dufferin Creek**, and spend the day walking and getting to know each other. 📱 Don't forget to join our **WhatsApp Group – [CLICK HERE](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** *** ## 🚶‍♂️ What We'll Do We'll start outside **Pioneer Village Station** and make our way through Black Creek Parkland before joining the Finch Recreational Trail. Along the way we'll: * Walk through Black Creek Parkland 🌳 * Follow the Finch Recreational Trail * Enjoy the fall colours and changing scenery 🍂 * Stop for a break near Dufferin Creek * Have some time for conversation and photos * Continue along the trail toward Finch Station This is a **long but easy, mostly flat walk**. There are no major hills or difficult terrain, but you'll want comfortable shoes and enough energy for the full route. *** ## 🍂 Fall Is the Best Time to Do This Walk There's something particularly nice about this trail in the fall. The air is cooler, the leaves are changing, and the open stretches of the trail give you plenty of room to slow down and enjoy the season. It's a good walk if you want to get outside without feeling like you're climbing a mountain. And as always, **the activity is the container. The people you meet along the way are the real experience.** *** ## 🧢 Meetup Details 📍 **Meetup Location:** Outside Pioneer Village Station, at the corner of Steeles Avenue West and Northwest Gate (East Side), in front of the York University sign. 🫎 **Look for me in my Moose Hat!** ⏰ **Meetup Time:** 11:00 AM sharp I will only wait **5 minutes**. **Early is on time. On time is late.** 🏁 **End Point:** Finch Station *** ## 🎟️ Meetup Fee **$5 cash in person or e-transfer** 📧 **mathewmaclean@hotmail.com** This fee helps support the group and allows us to continue organizing events throughout Toronto. *** ## 🎒 What to Bring 💧 Water 👟 Comfortable walking shoes 🥪 A snack or light lunch 🧥 A fall jacket or sweater *** ## 🌈 Who Is This For? This walk is great for: * Anyone who enjoys fall scenery * People looking for an easy, flat trail * Anyone who wants to get back into walking * People who enjoy exploring Toronto's green spaces * Anyone looking for a relaxed social outing * People who want to meet new people while getting some fresh air 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**. **Come for the fall colours.** **Stay for the friendship.** 🍁💛

Wilder Series: The Wilder Loop

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/wilder-loop-fall-26)** **The loop is back and more wild than ever!** For those unfamiliar, The Wilder Loop is 16 km of remote, rugged terrain through one of Ontario’s most untouched landscapes. Right from the start, the trail throws you into the wild: the first 5 km have everything we love about backcountry hiking; twisting forest paths, sweeping granite ridges, narrow boardwalks, and multiple beaver dams to scramble across. No two kilometers are the same, and every twist in the trail feels like a secret waiting to be found. Once we hit the loop section, things get much quieter. This part of the park sees very few visitors as human footprints give way to moose tracks, and the rustling in the brush might just be one of the many beavers that call this area home. Though the total elevation gain is relatively modest (about 260 m over the whole route), the trail’s difficulty comes from its remoteness, terrain, and ever-changing conditions. That said, for those willing to take it on, the reward is huge: sweeping views, total solitude, an unfiltered experience of Ontario’s boreal beauty... and a well-earned sense of pride by the time we make it back to the trailhead. ***Secret Location*** This is one of Wilderness Union's 'secret' hikes. As a group, we visit some truly special spots that are undiscovered by the wider world. We like to keep them pristine and only share them among our members- we ask that you do the same! We reveal the location to registered members in the days before the trip. **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** **Untouched Wilderness:** Step into a landscape that feels frozen in time; wild, windswept, and wonderfully remote. Just you, the forest, and the sound of your boots on the trail. **Wildlife Spotting:** Bears, moose, beavers and loons are just some of the creatures that call this area home. You'll have a chance to spot some from a safe distance for a magical encounter. **Beaver Dam Crossings:** The area we're visiting is shaped by beavers. Tiptoe across nature’s original bridges- muddy, meticulously built, and surprisingly sturdy **Event cost: $60+HST. $50 optional transport also available. Please register [here.](https://www.wildernessunion.com/adventures/wilder-loop-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/)***