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Challenging Hikes Toronto

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Long Sault Conservation Area hike

Long Sault Conservation Area hike

Fri, Oct 16, 9:30 PM
From Move With Intention
4.9

**I’m organizing a fall hike at Seaton Trail in Pickering October 16, at 5 30 p.m.** **We’ll aim for an 8–10 km hike, taking approximately 3–4 hours at a moderate pace, with breaks to enjoy the fall colours and take pictures.** **It should be a lovely opportunity to enjoy nature, get some exercise and meet new people.** **Bring comfortable hiking shoes, water and snacks. Let me know if you’d like to join!**

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2 attendees

Earl Bales Park Mountain Goat 🐐 - Challenging Hike ⛰️ ⛰️

Sun, Sep 27, 1:00 PM
From 2&4hr -Advanced Hikes TORONTO
4.9
2 attendees
Barbecue and Hike through Tommy Thompson Park.

Barbecue and Hike through Tommy Thompson Park.

Sun, Sep 27, 5:00 PM
From These Boots Are Made for Hiking
4.8

Location: Meet at the entrance of Tommy Thompson Park -Leslie Street Spit **It's time to have some fun!** What better way to celebrate the end of Summer with a barbecue by the lake. Join us for burgers and drinks **under the tents** and on the water at Ashbridges Bay for burgers and drinks! ($10. For a burger and drink.) After a 8km hike (with some fun things happening along the way) at Tommy Thompson Park we will head to Ashbridges Bay for burgers- veggie and meat. Feel free to bring alcoholic beverages, and board games - We will have a beach ball. Tommy Thompson Park is a man-made urban wilderness and wildlife sanctuary built on the Leslie Street Spit, stretching 5 kilometers to Lake Ontario. Managed by the Toronto and Region Conservation Authority, this unique park offers a peaceful escape from the city with a mix of wetlands, meadows, and trails. A unique place near downtown Toronto to experience nature, and *one of the best places for bird-watching in the city*, with more than 300 recorded species!

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107 attendees

HIKE - SOCKS - BEER (Bermuda Triangle)

Sat, Sep 26, 1:00 PM
From Trail Hike - Richmond Hill
4.9
12 attendees
HikeFit: Earl Bales – Steep Hills Fitness Hike – L3 (Moderate)

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

Wed, Sep 23, 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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4 attendees
Now For Something Arty!

Now For Something Arty!

Sun, Sep 27, 11:00 PM
From These Boots Are Made for Hiking
4.8

**Meetup: St. Mathews Clubhouse; 450 Broadview Ave.** So while we have a day event on the 27th, if you have an arty side, continue your day by joining me at St. Mathew's Clubhouse for an arty experience. While many of you know I am a writer by trade, I am also a painter. I'm just an arty girl! I have put together an Art Collective with 6 artists along with myself to showcase and of course sell our work but also enjoy Art, Wine & Inspiration — Come Create With Us! 🍷 Join us for a free collective art show celebrating creativity, connection and the joy of making art. And why just look at art when you can explore your own creativity too? Come discover what inspires you, try something new, and let your imagination wander. ✨ Art to explore. 🍷 Wine to enjoy; nibbles to share. 🥂 Hear from the.artists! 🎨 Creativity to discover. 💫 And best of all — it’s FREE

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34 attendees
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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.