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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

THE GOD OF HIKING sculpted a MASTERPIECE, and it's called: “HANGING ROCK”

THE GOD OF HIKING sculpted a MASTERPIECE, and it's called: “HANGING ROCK”

Sat, Nov 14, 10:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

To think that 3 Sisters is all the tourist rage in Blue Mountains when an easy 5kms Trail Hike takes you to a **HANGING ROCK** destination that can only be described as… *Stunning. Magical. Magnificent. Dangerous (can be). Unforgettable.* **The best view in all of The Blue Mountains? Hanging Rock is absolutely incredible.** Let’s hike it, and let’s add “Grotto Canyon”… a hidden, cool-calm waterfall in a cave-like setting. **THE HIKE. HANGING ROCK (pic on left)** Hanging Rock… last weekend, I didn’t know what to expect when I first hiked it. Sure, I’d seen the photos / videos, and it looked impressive. My advice to you? *Ignore the photos.* It’s so, so much more amazing in person. The sheer rock faces are incredible to be close to. The contrasting rock colours with the background green-ish Blue Mountains is so picturesque… 20minutes at Hanging Rock is a destination you won’t forget. And I wanna see it again. As far as easy hikes go in The Blue Mountains this one is it. It’s a flat 5kms out. 5kms back (we’ll move with passion). It’s a lovely fire trail journey with wildflowers and views in the distance…. And then? You can sense Hanging Rock is about to appear. And when it does, it’s “WOW!!!!!!” At this point the hike down brings some adventure… safety is key, but it’s all proper fun and amazing photos. **LUNCH.** Spikes Bistro is a great spot on Blackheath Golf Course for lunch and a post-hike beer. I’ve gotten to know the owner – the nicest Sri Lankan family, and their food is really good with top (they always give us the best table on the balcony) views over the golf course. The Sunday roast hit the spot, and the green curry is my order this time… These are damn good people, and I love giving them our business. **[JOIN WHATSAPP BY CLICKING ON THIS LINK. NO JOIN? NO HIKE. WE COMMUNICATE IN WHATSAPP.](https://chat.whatsapp.com/FzBLoAqHcUbBCgrV4EF4HT)** **HIKE #2. THE GROTTO (pic on right, yes I took it)** I’ll write less. Just grab my arm for this quick (it's Sunday after all) descent / ascent hike… what a treat. Many waterfalls we’ve seen are quite exposed. The Grotto? Hike down. Hike down again. Hike low through a bit of a cave, and there it is… a waterfall and rockpool hidden like a movie-esque scene where Ryan Reynolds & Scarlett Johanssen embrace, ass grab, and French Kiss in the cheesy final scene. It’s beautiful. *Drivers… we love you. We need you (of course you’ll be compensated). 6 cars, 3 passengers in each. 24 hikers max.* Ready yourself for a great fucking day. See you soon. MJ **THE RULES.** A) Safety. Be safe! No insta photos on cliff faces. That's out. B) Be fit, healthy, and able to keep up - exercise pace while chatting and laughing with other hikers. C) $15 Cash or PayID or PayPal. D) Be on time. If you're late, use the map to catch up. E) No shows and morning cancellations are slack. If you're in that group from past hikes, sorry in advance if you're moved into the "No" column. F) BYO water, towel, Band Aid, and snacks. G) Be fun. Active. Social. And ready to meet some new folks. H) Newbies. Feel free to join! But if a hiker that's been great with attendance asks to join, you might be moved into the "Not Going" column - apologies in advance for that. **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; 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; e) You’ve been advised to download the “Emergency Plus App” and f) 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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24 attendees
Great North Walk - Awesome Bushwalk from Chatswood to Thornleigh!

Great North Walk - Awesome Bushwalk from Chatswood to Thornleigh!

Fri, Nov 13, 10:30 PM
From Aussie Explorers
4.8

**This is a fabulous bush walk with plenty of picturesque sites to see along the way!** **The route follows the peaceful, non-tidal waters of the Lane Cove River, tracing the valley from the weir at Fullers Bridge all the way up to the northern watershed near Thornleigh.** **We meet outside Chatswood Train Station opposite McDonalds at 9.30am sharp.** **We start by walking through some local back streets to reach the Blue Gum Walking Track which will take us to the Lane Cove River National Park.** **We will then join the Great North Walk trail to Thornleigh.** **There are steeper sections and rocky dry riverbeds. The scenery is diverse - quintessential Aussie bush, honeycomb sandstone and mossy valleys. We will meander through this beautiful piece of quiet Aussie bush with shaded gullies and blue gums. We won’t even realize that Ryde and Macquarie Park are close by.** **There is a steep 100m climb at the end of the hike to take us to Thornleigh Oval and a further 15 minutes along suburban streets to reach Thornleigh Train Station.** **Please bring own lunch and snacks as there are no options to buy any food along the way.** **We will aim to finish at Thornleigh Train Station by 3.30pm.** **\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*** **DISTANCE: About 18 kms.** **GRADE: Medium, some rocky bits but mostly on established tracks. A couple of ascends.** **NOTE: No exit points.** **SAFETY WARNING: Please stay away from cliff edges and be very careful when walking on wet and slippery rocks and surfaces. Please stay within sight of the group at all times and do not walk in front of the leader. If you get lost, you are on your own and must find your own way home.** **IMPORTANT INFORMATION:** · **Be Prepared: Wear comfortable hiking shoes, bring at least 2 litres of water (plenty of places to top up), lunch, snacks and dress for the weather. Wear sturdy walking shoes, trainers or running shoes are fine.** · **Follow Instructions: Please follow the instructions of the Host at all times and keep the Host within sight.** · **RSVP Responsibly and Be Ontime at the Designated Meeting Point: Update your RSVP if you can’t make it.** **GRATUITY: $10 applies to this event which can be paid in cash on the day or PayID is 0439 344987 Cristian Sylvestre.** **\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*** **DISCLAIMER: Your health and safety is our priority and we take care to minimize risk and avoid accidents and injuries.** **However, Organizers and Hosts are not responsible for your health and safety and do not accept any liability for accidents and injuries that may occur during Meetup activities and events. Please take responsibility for your own safety and belongings.** **By RSVPing to this event you and your guests agree to comply with the terms and conditions of the Aussie Explorers Meetup group which can be found in the link below:** **[https://www.meetup.com/Aussie-Explorers](https://www.meetup.com/Aussie-Explorers/pages/28346396/Terms_and_Conditions_of_joining_Aussie_Explorers)** **\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*\*** **Any questions or concerns, please send me a TEXT message (0439 344 987) rather than unnecessary updates on the comments section.**

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26 attendees
Lane Cove River Hike... "French Gardens" to a Super Cool Aussie Pub!!!

Lane Cove River Hike... "French Gardens" to a Super Cool Aussie Pub!!!

Fri, Nov 13, 10:15 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**Lane Cove to Woolwich Pier Hotel.** It's a hike in National Park (start of The Great North Walk in fact). It's a river walk. Bush hike. It’s pretty flat and plenty beautiful. The stone cottages / architecture in Hunters Hill must be seen. And **Woolwich Pier Hotel** is a damn cool pub with one of the best beer gardens in Sydney... **THE HIKE.** Less words about this one… The first 7kms-ish is a lovely trail hike along Lane Cove River, and the final 3kms is a gorgeous neighbourhood walk through Hunters Hill and Woolwich (two leafy, wealthy communities). We start with a river crossing via a cool bridge and immediately head into a bush hike... part of The Great North Walk from Sydney to Newcastle. Some twists. Turns... Ups. Downs. It's really casual and really cool to be in nature so close to suburbia. When we exit the trail hiking, some incredible neighbourhoods take over the spotlight. These neighbourhoods are known for their... *"mid-to-late 19th-century and early 20th-century craftsmanship. Often dubbed a 'French Village' due to the mid-1800s development led by French brothers Didier and Jules Joubert, the area is recognized as one of Australia’s oldest garden suburbs."* And the final kilometre (post-pub) is through beautiful Woolwich to a perfect Sydney Harbour Ferry ride to Circular Quay... and another bar(!?!?!) in The Rocks perhaps? The hike is pretty flat, so we’ll move with decent pace to work off a week of caloric intake (I'll have a story about mine). *We meet at Lane Cove North (Epping Rd opp Mowbray Rd - 288 or 290 bus drops right there) Bus Stop at 930am! The bus stop is in a weird location -* ***[JOIN OUR WHATSAPP GROUP HERE](https://chat.whatsapp.com/KTnuC3SI5DWFNKKTjPGjda)****, and I'll pinpoint it for all of us.* **THE PUB.** **Woolwich Pier Hotel** is pretty much the perfect pub… with its inner-west charm & history, fireplace, beer garden, leather booths (oh yes, leather), live music, amazing food, and proximity to Sydney Harbour / ferry wharf. All that it’s missing is our “We Hike… to the Bar” group charm. This joint feels *lush,* *warm, and welcoming* from the moment your tired legs and ass hit the pub seat. ***It's also home to one of my worst Tinder dates of all time - if anybody reminds me at the start of the hike (or even reads this far down) I'll tell the story.*** Reservation made – my credit card is down, so I expect 100% participation if you RSVP “Yes”. Lovely hike. Top pub. See you there. MJ **THE DETAILS.** **WHATSAPP.** You’re not 100% confirmed until you’re in the whatsapp group. Join it 'cause we love it, we use it! Click on the link (above) – if not, sadly you’ll be removed from the event on MeetUP. **Cancels / No shows.** Treat your RSVP like a restaurant reservation. *No show / cancel on the day?* That restaurant is my hiking group – you won’t be welcomed in the future. Respect and manners matter as I put my credit card down for your reservation. Double booked with another group? Come on… be kind. **Gratuity.** $15 PayID or Cash. **Safety.** Let’s chat, let’s have some laughs… but let’s be safe. **Fitness.** Yup. Fitness matters for all of our hikes – especially if we are going into National Park. **Guests.** Bring mates, dates, co-workers. **Good energy, smiles, and laughs…** Bring ‘em all! You’re joining the most fun hiking group in Sydney. ***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; 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; e) You’ve been advised to download the “Emergency Plus App” and f) 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). g) Over 60yrs old, and new to the group? Send me a note first please.

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17 attendees
Blue Mountains Classic: Woodford, Red Hand Caves -Glenbrook - 28km (Hard)

Blue Mountains Classic: Woodford, Red Hand Caves -Glenbrook - 28km (Hard)

Fri, Nov 20, 8:20 PM
From Sydney Outdoors Meetup Group
4.7

**Blue Mountains Classic: Blue Mountains Classic: Woodford, Red Hand Caves -Glenbrook - 28km (Hard)** This epic Blue Mountains walk has the following sections: 1\. Woodford Train Station Wheel Gully Waterhole; 8km\, morning tea\. 2\. Wheel Gully to Oaks Picnic Area; 6km\, lunch/bathroom\. 3\. Oaks to Red Hand Cave; 7km\. 4\. RH cave to Glenbrook Train Station; 7km\. I aim to complete the day’s walking by no later than **5:00PM** This is a big day of spectacular walking, but we will be moving at a moderate pace so everyone who is interested to experience this serious bush walking track can attend and test themselves. **PLEASE NOTE: THERE ARE NO GET OUT POINTS - THIS IS A WILDERNESS WALK, FOR THE ENTIRE DAY.** **Distance:** 28 km **Type of Walk:** Fire trails and well-formed bush tracks. **Difficulty:** Hard **Walking Pace:** Average 4.5KM per hour to finish on time. **Meeting Place and Transport:** Catch the **7:24AM Blue Mountains Train,** departing Central Station from Platform 7. Members may join this service at Strathfield, Parramatta, Blacktown or Penrith. Our train arrives Woodford at 8:58AM. There are regular trains, every 30 minutes, back to Central from Glenbrook. **What to bring:** Good walking shoes/trail runners; 2-3 litres of water, NO WATER REFILL along the way; hydrolytes; two snacks and one lunch; light rain jacket depending on conditions. **THIS IS A MOUNTAIN WILDERNESS WALK, WITH NO SHOPS, SO MEMBERS MUST BRING ALL FOOD AND WATER.** **Suggested Donation:** $10 **By RSVPing to this event,** you (and your guests) agree to and are bound by the terms and conditions of SOMG which you can view here: https://www.meetup.com/sydney-outdoors-meetup-group/messages/boards/thread/53245383 **Questions?** Ask in the comment section. I will post my mobile number closer to the day. Ted :)

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11 attendees
🌳 North Shore Harbour Bushwalk - Artamon to Milsons Point ~16km

🌳 North Shore Harbour Bushwalk - Artamon to Milsons Point ~16km

Sat, Nov 21, 10:30 PM
From OZ Outdoors
4.8

**This is a 16-kilometre hike of North Shore's stunning bushland, streets and harbour through Gore Creek and Cremorne Reserve.** This walk features stunning scenery and historical sites with some elevation and stairs so a good fitness level is recommended. There are also multiple exit points. **Here's what you need to know before RSVP!** * This event is hosted on **[TrekMeet](http://trekmeet.com/),** a free offline hiking app without ads, I built with and for this community, and would love your support if you could [please ](https://trekmeet.com/event/b93681de-b914-4d50-bd9e-25467aef9e55?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2)**[RSVP here,](https://trekmeet.com/event/b93681de-b914-4d50-bd9e-25467aef9e55?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2) i**t has offline trail route and event chat. You can also search TrekMeet and **[join OZ Outdoors](https://trekmeet.com/group/oz-outdoors?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2),** **we're moving there in coming months.** * **Start time:** 9:30 AM sharp (please arrive 10 minutes early) * **Meeting point:** Outside Artamon Station, Wilkes Ave exit (near Lucky Mart) * **Difficulty:** Bushwalk, hills, stairs, streets and parks. **Easy-moderate for regular hikers.** * **Route:** We'll begin by walking to Artamon Reserve for Flat Rock Creek, followed by bushwalk sections to Tunks Park for a break. The next part will transition to street walks, taking us through Neutral Bay streets to Reid Park, and then to the scenic Cremorne Reserve. Our harbourside walk will continue through historic May Gibb's house and Sub-Base Platypus before finishing at Milsons Point Station. Route may vary slightly, and there are plenty of exit options if you need. * **What to bring:** Comfortable hiking sneakers (uneven terrain in some areas), water bottle (refills available during break), sunscreen, hat, weather-appropriate clothing, and your **snacks/lunch, late lunch at any local pub if you'd stay**! * **Gratuity:** A $5 gratuity is appreciated to cover organising costs. You can pay cash or via PayID at the event. **Important - Please Read:** * **What to Bring:** Wear proper hiking shoes, bring **ample hydration (1 litre, have refills along), enough snacks/lunch for the day,** sunscreen, hat and weather appropriate clothings**.** * **RSVP responsibly** – Treat it as a commitment; update or cancel 12–24 hrs before. * **Arrive early** – All route/gear info is in the description; hosts can’t field messages during the event. * **Stay together** – It's a volunteer-led community walk; keep the host in sight and let them know if you leave. * **Safety first** – **Your safety is your own responsibility**! You agree to follow host instructions, public-health orders and OZ Outdoors guidelines: [https://www.meetup.com/ozoutdoors](https://www.meetup.com/ozoutdoors) * **Connect with us on Instagram:** [https://instagram.com/ozoutdoors.syd](https://instagram.com/ozoutdoors.syd)

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8 attendees

Capertee Campground/ Navigation with maps / Car Camp Wknd

Fri, Nov 20, 6:00 AM
From Indigo Adventure Group - (Outdoor Activities)
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 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.