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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

Starlight Trail Hike

Fri, Oct 23, 11:00 PM
From Sydney Adventurers 20s-40s (OZ Adventurers)
4.7
4 attendees
BEST HIKE IN 'Straya? Blue Mountains GRAND CANYON HIKE. Pub Lunch & Beer.

BEST HIKE IN 'Straya? Blue Mountains GRAND CANYON HIKE. Pub Lunch & Beer.

Fri, Oct 9, 10:51 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

From TIMEOUT Magazine: *"One breathtaking bushwalk claimed the crown as the nation’s favourite. The gold medal went to the **Grand Canyon Track** – a challenging yet short hike through the lush rainforest of the World Heritage-listed Blue Mountains National Park. The 6.3-kilometre circuit passes gently cascading waterfalls, giant ferns and moss-covered rocky overhangs that look straight out of a fairy tale."* Yup. A fahkin' fairy tale that ends with a beer and lunch. (Moved this to October as more sunlight will make for a better day!) **THE HIKE.** It's a 6.3kms loop hike. NSW Parks estimates 3-4 hours, which means this hike is medium in difficulty (430m of altitude gain is a lot of steps, but it's not that bad when you're there). It's absolutely beautiful - waterfalls, greenery, views, and more. It's like somehow Mother Nature carved out this perfect crevasse - hiking it has you exiting civilisation into Jurassic Park-esque world. *Fitness matters here, but we will be hiking at a relaxed pace so we enjoy our surroundings.* Last time I had a video of the hike here. I deleted it. Just come. At Step #1 where we view Evans Lookout, it's truly a "Woowowowowowow" type start. It only gets better from there. **THE TRANSPORTATION.** A train arrives at Blackheath Station at 951am. Let's meet at the pub across the road. There's parking and toilets there. However, let's try to get enough drivers for this one. The train arrives in Penrith at 827am. **[Perhaps drivers pick us public transporters there? Let's discuss this all in the whatsapp chat that you must join on this hike!](https://chat.whatsapp.com/KngCa1lMtdUEAoSy6zXuGP)** **LUNCH.** "[Spikes Bistro](https://www.facebook.com/p/Spikes-Bistro-Blackheath-61574548437651/)" (where all the locals are going these days) is now a family run joint at the golf course with GREAT food. I'll make a reservation right on the same balcony we had last time! It's a perfect ending to The Grand Canyon, and the family is thankful to have our business. Let's support the locals who support us. **ANOTHER HIKE.** We'll have cars. Shall we do another short hike? I'm open. Charles Darwin Trek is newly open, and it's an easy one with top, top views of Wentworth Falls. Valley of the Waters? Another 10/10 waterfall hike. Or no doubt you'll be able to get a lift to Blackheath Station if you need to get home. **THE DRIVERS.** We need some drivers for this one. If you drive each passenger you take from will chip in some cash - I'll see to it. We looooove you drivers! **THE LOGISTICS.** a) Gratuity $15 Cash or PayID on the day. b) Let's try to start hiking by 1030am absolute latest. c) Last minute Cancels and No Shows... *I'm not even going to say it.* d) Have a backpack filled with... well, you know all this shit by now. Make a list. Be safe. Be smart. This will be a hike you won't forget - I can't wait to see the "Holy shit, WOW" look on all of our faces! See you soon. MJ 0439 635 699 **In pressing the “Attend” button for this hike, you acknowledge that:** a) You are healthy and fit to complete the hike describe; b) You have read and will follow [NSW National Parks Bushwalking Safety Guidelines](https://www.nationalparks.nsw.gov.au/safety/bushwalking-safety) for this hike; c) You have no chronic / underlying health issues that deter you from completing this hike; and d) You understand your host is just that – your host, not a professional hiker – and that you and you alone are responsible for your hiking health, safety, and wellness; and e) You’ve been advised to obtain individual [hiking insurance from 1Cover](https://www.1cover.com.au/adventure-travel-insurance/hiking-trekking/?utm_source=google&utm_source_platform=gads&utm_medium=cpc&utm_campaign=13564994076&utm_term=adventure%20travel%20insurance&gclsrc=aw.ds&gad_source=1&gad_campaignid=13564994076&gbraid=0AAAAAD_bfRAu6Io5ZkHeiIYCP_evtsQ_z&gclid=CjwKCAjwz5nGBhBBEiwA-W6XRLm8Itjn1am8sdPMxVhBtRmsDOWkolLlVATJcXW5jW-9JgB7hb9kMhoC7M0QAvD_BwE).

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31 attendees
HIKEFit_EXpress - Summit Sessions

HIKEFit_EXpress - Summit Sessions

Tue, Oct 6, 7:30 PM
From Sterling Fitness Hiking Adventures
4.9

**Feeling unsure about hiking?** You’re not alone. Many new hikers worry about endurance, steep trails, or what gear to use. **HIKEFit_EXpress – Summit Sessions** is designed to help you start hiking confidently — at your own pace — while building fitness, strength, and trail skills. ## **What You’ll Do in Each 60-Minute Session** **40 Minutes of Guided Hiking** * Explore beginner-friendly local trails * Build stamina gradually without feeling overwhelmed * Enjoy the outdoors in a supportive, encouraging environment **20 Minutes of Strength & Balance Training** * Exercises to support hiking muscles * Improve stability, flexibility, and injury prevention * Perfect for all fitness levels ## **Learn More Than Just Fitness** In **Summit Sessions**, you’ll also: * Get essential **gear tips** for safe and comfortable hikes * Discover **local trails** perfect for beginners * Learn about **longer hikes and international treks** so you can plan future adventures with confidence * Connect with a friendly community of fellow new hikers ## **Why Join HIKEFit_EXpress – Summit Sessions?** * Build endurance and strength **gradually**, without pressure * Gain confidence to tackle your first 2–3 hour hike * Learn skills that make hiking enjoyable and safe * Start your mornings energized and inspired

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1 attendee
WE HIKE... to the YACHT PARTY OF 2026!!!

WE HIKE... to the YACHT PARTY OF 2026!!!

Fri, Oct 16, 11:00 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**WE HIKE TO THE YACHT PARTY 2026** **SATURDAY, 17 OCTOBER 2026** **(Yup. That pic is our yacht! Look at it!)** Here we go team... you asked for it. We provide it. Last year was super, super fun. We Hike to the Bar has doubled in size, so *"You're gonna need a bigger boat..."* So. We got a bigger boat. More fun. More chaos. More memories. Newbies, guests feel free to join in - always more fun if you come on a hike with us leading up to the event. Here we gooooooo! **SCHEDULE OF EVENTS:** 10AM: \*\*3HRS (OPTIONAL) SYDNEY HARBOUR HIKE 1PM: \*\*ONE HOUR TO CHANGE, BYO FOOD, BYO DRINKS. 2PM: \*\*DEPART KING ST WHARF ON WHITEHAVEN 5PM: \*\*ARRIVAL KING ST WHARF 530PM: *AFTER PARTY AT HELM BAR, OUTDOOR TERRACE* [ALL PAYMENT DETAILS, ETC WILL BE DISCUSSED IN OUR WHATSAPP GROUP. CLICK ON THIS LINK - YOU MUST JOIN (if you registered your interest you are already in there).](https://chat.whatsapp.com/Ig0MHnm7TLFFC1rupyF28N) **WHITEHAVEN** (55 foot Catamaran, up to 70 hikers, 2 spacious decks, lounge seating, quality sound system, swim ladder) **PRICE: $110**. Payment info will be in the whatsapp group. Includes the hike, the yacht + 2x wharf fees, BYO food fee, BYO booze fee, 3x staff fee, BBQ fee. I’ll bring 1x sausage / bun for all, crisps, and salads for the vegetarians. *Sorry no refunds, but tickets are transferable (expecting a waitlist for this one)!*

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57 attendees
Hanging Rock, Blue Mountains

Hanging Rock, Blue Mountains

Wed, Oct 7, 8:00 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**Ya know what’s well hung? Rocco Siffreddi. Florida. And Hanging Rock.** One is in Italy. The other the USA. And the last that’s the shining star in this event just 1.5hrs from Sydney? The Blue Mountains. Hanging Rock looks crazy. Looks fun. Looks like we should check it out. NOTE. This is only a “I’m interested in this adventure” at this stage. The event is not on a Wednesday - it's just to gauge interest. We'll plan it / we’ll do this event with no more than 20 hikers. And of course... with a beer to "Cheers" at the end. Politely stating: if you’ve not hiked with the group before this event won’t be for you. I need to know your skill / ability. Please don't sign up if I don't have your mobile / haven't been on hikes before. Interested in some proper adventure? Sign up!

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23 attendees
🌲⛰️ Popes Glen, Govetts Leap & newly reopened Pulpit Rock Lookout 🌲⛰️

🌲⛰️ Popes Glen, Govetts Leap & newly reopened Pulpit Rock Lookout 🌲⛰️

Fri, Oct 9, 11:40 PM
From Live Big! Sydney Walking and Social Meetup
4.7

⚠️ FOR YOUR SAFETY & ENJOYMENT, PLEASE READ DESCRIPTION BELOW FULLY BEFORE YOU CLICK ‘Attend’! ******************************************** 🗓 DATE: Saturday, 10 October 2026. ⏰ MEETING TIME: 10.40am. 🚊 MEETING POINT: Blackheath station (start & finish), Great Western Hwy entry/exit. 🌍 Please use Google maps for exact location, not Meetup maps! ******************************************** 🥾 DISTANCE: 16km return. 🥾 GRADE: Moderate on a steady pace, not snail pace! 💪🏽 Reasonable fitness recommended due to uneven rocky surfaces, ups and downs hills, lots and lots of steep stairs, creek crossings, rock scramblings and a bit of bush bashing at few overgrown sections. 💪🏽 Tracks expected to be wet, muddy and slippery in parts. 📸 WHAT TO EXPECT: 🚶‍♂️Upon arrival at Blackheath station, we will proceed immediately on a local roads via Popes Glen and Govetts Leap with amazing views of the waterfalls and Grose Valley in Blue Mountains NP. ℹ️ Pulpit Rock Reserve in Blackheath has now reopened following major restoration works, including improved access, picnic facilities, accessible amenities and upgraded walking tracks. https://www.bmcc.nsw.gov.au/media-centre/pulpit-rock-reopens-after-major-upgrade 🚶‍♀️From the platforms that remain, the view is the one that made Pulpit Rock a favourite. It is an almost 360-degree sweep across the Grose Valley to Govetts Leap and the Blue Gum Forest, with cliff lines stretching out to Mt Banks. https://www.nationalparks.nsw.gov.au/things-to-do/lookouts/pulpit-rock-lookout 🥪 We’ll have a lunch break at the revamped picnic area soaking up the magnificent views with lots of photos and selfies. 🚶Depending on the day, we may visit a “secret cave” on our way back to Blackheath station. Shhhh! 🤫 ⚠️ IMPORTANT INFORMATION ⚠️ 📝 TERMS & DISCLAIMER: ℹ️ Attending this event is voluntarily at your own risk. Organiser/s accepts no liability of any kind including injuries, accidents, misadventure etc during and after this event. ℹ️ For full disclosure on Public Waiver, please refer to Meetup Terms and Conditions and the front page of this group on ‘About Us’. ✅ You must assess your own fitness and ability before participating in this event. ✅ You are responsible for looking after your own health, safety and belongings. ✅ You must adhere and follow the instructions from your organiser/s at all times during this event. ✅ You must take personal accountability for your own choices, actions and/or misadventure. ❎ If you’re not sticking with the group or getting lost during the walk, you’re responsible for finding your own way out. The group DO NOT wait for you! ✅ You must also take care not to put other people at risk. ✅ Keep well back from cliff edges at all times, especially when taking photos. ❎ NO facilities or cafes on the trails, so please come well prepared. ❎ NO smoking of any kind on the walk including during photo stops and lunch break. ❎ If you do not wish to be photographed (randomly or group photos), please DO NOT join this event! ✅ Please be mindful and respectful to members and guest/s from diverse backgrounds. This is not a dating event. ✅ If something’s come up, please Edit your RSVP to ‘Not Going’ asap at least by 7pm the day before. It’s only take a second!
❎ Late cancellation or No Show would not be tolerated. You will forfeit the opportunity to join my future events! ******************************************** 🎒WHAT TO BRING 🎒 👕 Comfortable outfit for the weather preferably hiking gear. Jeans or cotton t-shirt is not suitable for this walk. 🥾 Waterproof hiking boots or good grip walking shoes/trail runners highly recommended. 💦 At least 1.8L of WATER, Hydralyte or sports energy drinks. 🥪 Snacks and packed LUNCH. 🧢 Hat, sunscreen, insect repellent ie: Bushman or Aerogard and hand sanitiser. ⛑ Basic First Aid Kit ie. BandAids, bandages, antibacterial wipes etc. 🧥 Light raincoat or a poncho just in case of wet weather. 🤩 Great sense of fun and adventure. ℹ️ This is a great article tips on preparation for Day Walk Skills & Gear. Bushwalk Skills 101: https://www.bushwalk.com/article/8398 💵 GRATUITY/CONTRIBUTION: $10 CASH per person for this event to be collected at the start of the walk. ✅ Please bring correct change on the day to speed up the meet and greet. 📲 Or PayID to my mobile: 0405038557. Ref: (your Meetup name) & Pulpit Rock. ******************************************** 🚊 Check Opal Trip Planner for public transport services, weekend trackwork etc. https://transportnsw.info/ 🚗 Carpark on Station Street near the entry/exit or side streets. 🏃‍♂️ Please leave home with plenty of travel time and arrive promptly. If you’re running late, we don’t wait! ******************************************** ✍️ I will update further information during mid week on weather forecast, train schedule from Central etc. Check latest update on comments section before heading out. 📲 Any questions, please send me a TEXT message instead to avoid any confusion with unnecessary updates on comments section. 🌿 Let’s explore and enjoy the great outdoors! 🌿 Norra 😎 📱0405038557 (TEXT & PayID only)

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11 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 individuals through local groups and events based on shared interests, from hiking to tech meetups. It's a platform for building real-world connections.

Just search by interest and location on Meetup to find active hiking groups in Sydney, offering various trails and hiking events for different skill levels.

Yes, Sydney offers numerous challenging hiking trails accessible via Meetup events, catering to experienced hikers seeking adventure in scenic locales.

Organizers plan the hikes, providing event details like difficulty and location. RSVP to join and connect with other hiking enthusiasts.

Definitely! Join as many hiking groups as you like to explore different trails. Meetup encourages diverse participation based on your interests.

Yes, RSVP through Meetup ensures your spot in hiking events and helps organizers manage the group size efficiently for a better experience.

Meetup helps people connect through events but cannot guarantee outcomes like meeting a specific number of people or certain event conditions.

Absolutely. If you’re inspired to lead a hike, you can become an organizer on Meetup, creating and hosting your own events for others to join.

You’re likely to meet a mix of experience levels. Meetup groups often have seasoned hikers who can share insights and guide less experienced members on challenging trails.

Many are, but some events may be virtual if organizers opt for online gatherings, such as planning sessions or sharing hiking experiences.

Meetup focuses on group activities, so while it encourages group hikes, it doesn't cater to organizing solo expeditions.

Some groups arrange less challenging and family-friendly hikes. While this page caters to challenging hikes, Sydney has a variety of hiking options.

Bring essentials like water, sturdy boots, snacks, and a map or GPS. Organizers often supply detailed recommendations for each event.

Event quality varies. While most are well-planned, it depends on the group's organization and the leader's experience. Checking reviews can help gauge a group.

It's advisable to RSVP. Not only does it ensure you're expected, but it also helps organizers notify attendees of any changes or special instructions.