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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

Mount Kuring-gai to Berowra Station

Mount Kuring-gai to Berowra Station

Fri, Nov 6, 11:00 PM
From Hornsby walking and Hiking

🥾 What to Expect on the Hike 📍 Meeting Point We’ll meet outside Mount Kuring-gai Station and then walk together to the trail starting point. 🥾 The hike It is approximately 9.5 km, with a mix of uphill and downhill sections and some uneven bush tracks. We’ll keep a comfortable pace and take short breaks along the way to enjoy the scenery. It’s a moderate bushwalk, so please come prepared with comfortable walking/hiking shoes and enough water. 🌿 What You Might See Depending on the day, we may spot: 🦎 Water dragons 🐦 Different types of birds 🐟 Fish in the water 🌳 Beautiful native bushland 🏞️ Scenic views of the surrounding valleys and waterways 🎒 What to Bring 💧 Plenty of water 🍎 Fruit, snacks or protein bars if you’d like 🥾 Comfortable hiking shoes with good grip 🧢 Hat and sunscreen 🎒 A small backpack 📱 Phone with enough battery + power bank if you have one 👋 How to Find the Group We’ll meet outside Mount Kuring-gai Station before starting the walk. I’ll be at the meeting point, so everyone can easily find the group. (I take a train from Hornsby, if you live this side then you can join me here as well) Most importantly, come ready for a 9.5 km adventure, beautiful scenery, good conversation and a fun day outdoors! 🌿🥾😊 Note: This is not a guided walk/hike. It’s simply an opportunity for us to enjoy the hike together and keep each other company. I’ve done this hike before, so I’m familiar with the route and will help us stay on track. 🥾🌿😊

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1 attendee
CAVES BEACH, GHOSTIES BEACH… Central Coast Coastal Adventure!!!

CAVES BEACH, GHOSTIES BEACH… Central Coast Coastal Adventure!!!

Sat, Nov 7, 8:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

During my 3 Years of hosting **We Hike to the Bar** there's been quite a few jaw-dropping moments of scenery... **Ghosties Beach** and its caves is most likely the top moment of 2026. Legend Hiker Heidi (90+ hikes) and a few others mentioned some Newcastle hikes, and while researching - I just can't find a lot. If you have some suggestions, please send them to me. What did I find is a tad closer to Sydney, and this will be a gem of a 15kms coastal journey... **GHOSTIES BEACH - CAVES BEACH - SWANSEA HEADS** Low tide is 230pm (essential for Ghosties Beach caves), so here's how we'll hike **Swansea (north) to Catherine Hill Bay for lunch (cars parked here)... then finish with the short and beautiful Ghosties Beach Cave loop!** From AI (sorry, I hate using it), the highlights: * **Ghosties Beach Sea Cave:** A massive, dramatic rock tunnel and sea cave system located at the southern end of Ghosties Beach. (Note: It must be explored strictly during **low tide** for safe access). * **Pink Caves:** Vibrant, naturally pink-hued rock formations and coastal sea caves near Catherine Hill Bay. * **Scenic Coastline & Beaches:** Sweeping views of the Pacific Ocean and passes past several picturesque spots including Pinney Beach, Catherine Hill Bay, and Moonee Beach. * **Vantage Points:** Elevated headland views looking up and down the New South Wales coastline. We'll need drivers. Of course! We love you. I think good pick up points are Parramatta, Wolli Creek, and Chatswood. It's a 1hrs 20min drive from Chatswood. We'll start with those 3 locations and work from there. **Catherine Hill Bay Hotel "The Catho"** is a heritage-listed (from 1875) joint with really good food... as soon as you look at this pub, you won't forget it. It's a classic, and there's nothing like it. This looks to be a great day out... See you soon. MJ **THE LOGISTICS.** a) Gratuity $15 Cash or PayID on the day. b) Drivers, you'll be compensated by your riders. Thank you! 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. ***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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25 attendees

Olympic Pool hike and swim

Fri, Nov 13, 10:00 PM
From Sydney Adventurers 20s-40s (OZ Adventurers)
4.7
1 attendee
Great North Walk Mt Kuring Gai to Hornsby via Berowra 22km med-hard

Great North Walk Mt Kuring Gai to Hornsby via Berowra 22km med-hard

Sat, Nov 7, 9:30 PM
From Aussie Explorers
4.8

Fantastic 22.3 km one-way trail from Hornsby to Mount Kuring-gai traverses Berowra Valley National Park and includes sections like the Blue Gum Walk and Tunks Ridge Reserve. Expect varied terrain with steep sections, particularly as you approach Mount Kuring-gai, where you'll encounter panoramic views. The route also passes by Fishponds and Berowra Creek. Be prepared for a challenging hike that requires stamina and resilience, especially during the final ascent. A few ups and downs and a good challenging walk, finish with a cold beer in Hornsby RSL $10 fee applies to this event payable cash on the day or PayID is 0402 251036 David Matthews Please bring a sense of adventure, fun and of course suncream, hat, jacket in case of a change in weather, at least 2L of water, lunch, snacks and sturdy walking shoes 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 RSVP 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/pages/28346396/Terms_and_Conditions_of_joining_Aussie_Explorers](https://www.meetup.com/Aussie-Explorers/pages/28346396/Terms_and_Conditions_of_joining_Aussie_Explorers)

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19 attendees
Coastal Escape: Manly North Head Circuit, wormhole and beyond ~12/15 km

Coastal Escape: Manly North Head Circuit, wormhole and beyond ~12/15 km

Sat, Nov 7, 10:30 PM
From OZ Outdoors
4.8

Join us for a stunning coastal adventure where we’ll explore the North Head Circuit and the surrounding coastline. This route offers **spectacular ocean and harbour views, WWII history at North Fort, and local wildlife**. Depending on the weather and group pace, we will also navigate the “**secret wormhole” tunnel linking Manly to Freshwater,** followed by an optional extension towards Dee Why or a return to Manly for a late lunch. Due to the total distance (12–15 km) and a steady pace, good fitness is essential. **Before you RSVP, please read the details below:** * 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/44f41258-f247-45b8-b111-30a30ff336b9?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2)**[RSVP here,](https://trekmeet.com/event/44f41258-f247-45b8-b111-30a30ff336b9?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:** 8:45 AM outside Manly Wharf. Meet at the Seashell Sculpture in front of The Felons Seafood restaurant. * **Difficulty:** Moderate–Hard due to the undulating terrain, stairs, some steep sections, and a steady pace of \~4 km/h with short breaks. * **Route:** Starting at Manly Wharf, we will complete the 11 km North Head Circuit. We will then head towards the "secret wormhole" tunnel. If the weather is pleasant, we will tackle the rocky path through the tunnel to Freshwater Beach, returning to Manly via the B2M path. On a hotter day, we will visit the wormhole and return to Manly via an easier path. We will finish at Manly, where you can catch the ferry back to the city or stick around for a swim and a well-earned late lunch! * **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 (1.5 litres, we have refills), enough snacks/lunch for the day,** sunscreen, hat, swimmers (if you decide to take a swim), and weather appropriate clothings, recommended to carry **basic first-aid and insect-repellent spray.** * **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
Bondi to Rose Bay - Part 1 of Great Coastal Walks

Bondi to Rose Bay - Part 1 of Great Coastal Walks

Sat, Nov 7, 8:30 PM
From Off Peaks Club
4.9

Bondi to Rose Bay is a beautiful walk with great scenery. It is best to wear walking shoes or trail runners, as most of it is on public roads/paths. It starts easy, but those steps up and down after 15km or so are still a good work out! It is possible to walk back to the start from Rose Bay (approx 25 minute walk) There is also public transport back to the City, or (potential) car-pooling back to the start. 7:30am start on the beach side of Bondi Pavilion. See ([WhatThreeWords](https://what3words.com/grades.pirate.flown)[ ](///fish.clubs.shots)) for exact start location or look for Chris and his Akubra Public transport option is Route 333 from Martin Place Stand E at 7am (Bondi Junction stand A at 7:17am), gets into Bondi Beach a 7:26am There are also multiple options to drop out early if needed. Also it is getting hotter - hat, sunscreen, 2L or more of water are recommended. Note: We will soon only be on TrekMeet. Get the app now [trekmeet.com](trekmeet.com) See you there

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2 attendees
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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.