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Challenging Hikes Toronto

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The Queen Hike (18 km anniversary hike)

The Queen Hike (18 km anniversary hike)

Sat, Jul 25, 5:00 PM
From Hike to Eat
4.7

**Attendance policy is enforced for this hike**. See below for details. To celebrate our anniversary, we're hiking the entire length of Queen Street. Since Queen Street is *only* 14.3 km, we're continuing along the lakeshore to Etobicoke. Incidentally, this is the shortest route possible between Scarborough and Etobicoke. Queen Street runs through some of the most iconic neighbourhoods in Toronto: idyllic The Beaches, hip Leslieville, sketchy Moss Park, historic Old Town, bohemian West Queen West, and shabby chic Parkdale. The route buzzes with activity and attractions. And more importantly, acclaimed restaurants and bakeries featuring food from six continents. You need to be in decent shape and have a good appetite to do the entire route. However, as with other hikes, you are free to join and leave at any point. Those who walk the entire length of Queen St (Fallingbrook Rd to Roncesvalles Ave) will be eligible to buy a commemorative T-shirt (expected price \~$23). There are different dinner options at the end of the hike. 1. Modern Chinese. [Reserve your spot at Tis Two Cities](https://www.meetup.com/hike-to-eat/events/315259938/). 2. Asado (grilled steaks and meats): [Reserve your spot at Vos Restaurante Argentino](https://www.meetup.com/hike-to-eat/events/315260441/). 3. Panuzzo and pizza at San Vito's Bakery. Walk-in. 4. Sushi at Krazy Roll. Walk-in. [See all our past hikes](https://www.google.com/maps/d/edit?mid=1_FpYriQNv5okUB-oiCODi56uiRDgPGI&usp=sharing). **Highlights** Segment 1: The Beaches 1. Start (or end) of Queen St at Fallingbrook Rd (depart 1pm) 2. R.C. Harris Water Treatment Plant 3. Bagels on Fire / Fox Theatre 4. XOLA / Kyouka Ramen 5. Beaches Library 6. Tiflisi / Limon / Inmigrante 7. Toronto Fire Station 227 / Delina 8. Holi Taco / Dulcinella (arrive 1:58pm; depart 2:15pm) Segment 2: Leslieville 1. Dirty Birrias 2. Ashbridge Estate 3. Sweet Bliss Bakery / Hastings Snack Bar 4. Descendant Detroit Style Pizza 5. Kristapsons' Smoked Salmon 6. Ocha's / Leslie’s Sandwich Room 7. Tabule / Amber Kitchen and Coffee 8. Lamoon Thai Kitchen & Coffee 9. The Broadview Hotel / Happy Burger / White Lily Diner 10. Elviras (arrive 3:16pm; depart 3:33pm) Segment 3: Moss Park 1. Queen Street Viaduct 2. Los Gyros 3. Kim's Convenience 4. Moss Park Armoury / Panemor 5. Eaton Centre 6. Old City Hall / City Hall / Osgoode Hall 7. Campbell House Museum 8. Aux Merveilleux de Fred / Alpha's Shawarma 9. Mizzica Gelateria & Cafe 10. Banh Mi Boys / Yukimi Donburi (arrive 4:43pm; depart 4:56pm) Segment 4: West Queen West 1. Ramen x Remix / Bagels on Fire 2. Mico Italian Sandwiches / Maison 118 / Ngogo / North of Brooklyn 3. Sud Forno / Sanko Trading Co 4. Trinity Bellwoods Park 5. Forno Cultura 6. King Slice / DoDoner / Lisgar Park 7. The Grand Order of Divine Sweets / Han Kki 8. The MoMo House 9. Garleek Kitchen / Afrobeat Kitchen 10. Katyn Monument (arrive 6:20pm; depart 6:35pm) Segment 5: Sunnyside 1. Roncesvalles Pedestrian Bridge / Palais Royale 2. Sunnyside Dinosaur Playground 3. Sunnyside Pavilion 4. Trans Canada Trail Pavilion 5. Humber Bay Arch Bridge / Sheldon Lookout 6. Krazy Roll 7. San Vito's Bakery / Tis Two Cities (arrive 7:30pm) **Neighbourhoods** Fallingbrook > The Beaches > Leslieville > Riverside > Moss Park > Old Town > Downtown Core > West Queen West > Parkdale > Sunnyside > Humber Bay Shores **Map and terrain** [https://www.google.com/maps/d/edit?mid=17oNClOxL7LtZ7hqQv9AFxtxVDjozisU&usp=sharing](https://www.google.com/maps/d/edit?mid=17oNClOxL7LtZ7hqQv9AFxtxVDjozisU&usp=sharing) Portions of Queen Street have narrow sidewalks and lots of people. Since we're a big group, you can pick between the north and south sides of Queen St to walk. The map shows which side has better food and attractions but the other side may have interesting stuff too. We're walking westwards in the afternoon, so bring sun protection. **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.

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100 attendees

Sunnybrook - Don River ADVANCED Hike 🌻

Sun, Aug 2, 1:00 PM
From 2&4hr -Advanced Hikes TORONTO
4.9
8 attendees

Earl Bales Park Mountain Goat 🐐 - Challenging Hike ⛰️ ⛰️

Sun, Aug 9, 1:00 PM
From 2&4hr -Advanced Hikes TORONTO
4.9
4 attendees
Chasing Hilton Falls: A Summertime Hike

Chasing Hilton Falls: A Summertime Hike

Sat, Aug 1, 1:00 PM
From Wilderness Union Toronto - Outdoor Adventure and Hiking Club
4.7

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/hilton-summer)** **Hilton Falls is one of the best hiking spots close to Toronto, and we’ll be heading there with the crew to take it all in!** The route blends two very different trail personalities into one amazing adventure. The Beaver Dam Trail is wide and relaxed, threading past active beaver ponds and along the Niagara escarpment. If we’re lucky, we may see some of these incredible creatures at work. From there, we move on to the Hilton Falls Side Trail, which becomes a more technical, Bruce Trail singletrack with rocks and roots that make you pay attention to where you’re stepping, along with beautiful views from atop the escarpment. The waterfall is the centrepiece of this hike: a 10 metres fixture that flows over a rocky ledge into a pool flanked by the stone ruins of three 19th-century sawmills. It's one of the better pieces of trail-accessible industrial history anywhere close to the city. Good company, good trails, and an unforgettable day. See you there! **Highlights** **Hilton Falls:** A 10-metre drop over the Escarpment edge, framed by the stone ruins of three 19th-century sawmills. **Beaver Ponds:** Active beaver ponds and wetlands along a tributary of Sixteen Mile Creek. Move quietly and you might spot reptiles, amphibians, and a lot of beaver handiwork up close. **Close to the City:** Our Trailhead sits less than an hour from downtown Toronto. **Event cost: $50+HST (for explorer members) - $40 optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/hilton-summer)** **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/)***

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3 attendees
HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

Wed, Jul 22, 10:30 PM
From Ready, Set, Trail
5.0

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

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3 attendees

Train & Barenaked Ladies with Matt Nathanson

Tue, Aug 4, 10:45 PM
From Hiking, Cycling, and Fun with Friends
4.9
5 attendees
430kMonthly events
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60mMembers
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4.5App store rating
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200kGroups
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Frequently asked questions

Meetup connects people through shared interests. Whether you're into hiking, tech, or a particular hobby, it helps you find events and groups to join.

Use Meetup to search for hiking events in Toronto. You can filter by the activity type to find challenging hikes that match your experience level and interest.

Yes, there are several hiking groups in Toronto. These groups organize regular events and hikes, including challenging ones, allowing you to meet other outdoor enthusiasts.

Absolutely! Meetup lets you join as many groups as you like. It's a great way to increase your chances of finding hikes that meet your interests and schedule.

Some hikes may require special gear based on their difficulty. Always check the event details on Meetup, which often include gear recommendations from the organizers.

Many Meetup events are free, but some may have a fee. It varies by event and organizer, so check the event's description for specific details.

Once you find a hike you'd like to join, click on the event and use the RSVP button to indicate your attendance. It's simple and updates the organizer immediately.

Meetup covers a variety of activities, from relaxed to challenging. Join groups and choose events that fit your interest; challenging hikes are just one option.

Yes, if you're interested in leading a hike, you can organize an event on Meetup. You'll need to start your own group or join one as an organizer.

While Meetup brings together people with common interests, the level of expertise varies. Engaging actively helps meet people aligned with your hiking skill level.

Meetup encourages group interaction which can be safer, especially for challenging hikes. Always follow event guidelines and connect with others at the event.

Meetup facilitates connections but can't control weather or trail conditions. Always check local reports and prepare accordingly.

Availability of hiking events may vary by season. Toronto has active outdoor communities, but check regularly to see upcoming hikes.

Most hikes are in-person, and group meetings are scheduled to explore trails together. Always check event details, as some activities might also be virtual talks or preparations.

Absolutely. While this page focuses on challenging hikes, Meetup caters to all skill levels. Look for beginner-friendly groups and grow your skills with others.