Challenging Hikes Sydney
Find thrilling hiking adventures in Sydney

"WOW" Session: 12kms Flat Rock Gully to Spit Bridge! "Cheers" @ Pub to Finish!
Fri, Oct 30, 11:00 PMOver the past 3 years, I hope I’ve earned your trust when I say things like: a) *“You are going to looooove this bar”;* and b) *“Wow. This hike is a secret gem you’ve gotta try.”* *Well, this hike … is a really, really cool session all hikers in this group should experience.* (Edit: Shiiiit this event is popular. So? Two things: a) A reservation is made for us at **Las Palmas... a very cool Mexican Garden Bar in Manly**. When we finish the 144 bus is right there - 10min away is Manly Beach. b) DIY research, but the **Surf Sound Festival** is on in Manly Beach. Perhaps there's something you'd like to see!) **THE HIKE. Artarmon Station to Spit Bridge** At first, I didn’t know what to hike to plan, so I went on my hike-map creator app and just started connecting dots from Artarmon Station… east… via this creek. Via that park. Via this neighbourhood. And onward down to Middle Harbour which then linked to Spit Bridge. Looked like a nice 12kms through the middle of Sydney, but who knows eh? Then we hiked it. 28 of us hiked it on 11 October, and not one hiker had done the entire journey prior to. At the end? ***“WOW what a great, beautiful hike / never seen this pretty side of Sydney”*** echoed throughout. It’s truly a sneaky gem of a session – we were all surprised at the beauty from start to finish. [(TEAM: AFTER YOU HIT ATTEND, COME BACK HERE AND CLICK ON THIS LINK TO JOIN OUR WHATSAPP GROUP. IT’S A MUST TO JOIN THIS EVENT. I’LL BET $1,000 SOMEBODY WRITES ME AND SAYS “I CAN’T FIND THE LINK TO WHATSAPP IN THE EVENT”… AND WELL. HERE IT IS DUMMY!) CLICK HERE PLEASE? PLEASE! ](https://chat.whatsapp.com/JNPBdp3OzBS3rIUW8VgbB1)*[ALL SAID WITH A SMILE.](https://chat.whatsapp.com/JNPBdp3OzBS3rIUW8VgbB1)* ***Artarmon to Flat Rock Creek to Tunks Park and Middle Harbour, this hike zigs and zags out of gorgeous bushland and beautiful homes / architecture in the lower north shore. The finale is a lovely coastal, bush hike down to Spit Bridge where the bus will get us to the pub (to be named later – but it’s 100% on).*** There are some ups, some downs. But Artarmon (85metres above sea level) to Spit (sea level) is a downhill walk / hike. More in our group gotta see this 12kms Middle Harbour stunner. Get in there like swimwear. 1015am start (yes, a sleep in), and we'll finish hiking at 130pm, pub by 145pm. See you soon. MJ **THE LOGISTICS.** a) Gratuity $15 Cash or PayID on the day. b) Let's try to start hiking by 1015am 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. **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).

CAVES BEACH, GHOSTIES BEACH… Central Coast Coastal Adventure!!!
Sat, Nov 7, 8:30 PMDuring 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.
Olympic Pool hike and swim
Fri, Nov 13, 10:00 PM
Great North Walk Mt Kuring Gai to Hornsby via Berowra 22km med-hard
Sat, Nov 7, 9:30 PMFantastic 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)

Coastal Escape: Manly North Head Circuit, wormhole and beyond ~12/15 km
Sat, Nov 7, 10:30 PMJoin 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)

Jacaranda Blooms Walk 🌸 Milsons Point to North Sydney ~12KM
Sat, Oct 31, 6:00 AMThe Lower North Shore is turning purple and we've launched TrekMeet. Join us for our annual special **Jacaranda walk while celebrating TrekMeet launch,** and exploring the famous and secret bloom spots across Sydney’s north shore. Expect moderate hills, some stairs, and a steady pace of around **4 km/h** with photo stops along the way. **Good fitness is recommended, and keep your phone/camera charged for plenty of Jacaranda photos!** 🌸 There are multiple exit points if needed. **Before you RSVP, be sure to read the following:** * This event is hosted on **TrekMeet,** 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/9eb21368-6369-43c2-8621-1c8df20043d4?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2)**[RSVP here, no waitlist](https://trekmeet.com/event/9eb21368-6369-43c2-8621-1c8df20043d4?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2), or search TrekMeet and join OZ Outdoors**. Our group is moving there in coming months, and we use the app to share live location and chat at one place. * **Difficulty**: Easy to Moderate. Urban streets, parks and a few inclines. * **Start at 5:00 PM (arrive by 4:50 PM)** outside Milsons Point Railway Station (Kirribilli side) - Ennis Road. **Finish at North Sydney**, near the metro/station. * **Route:** We’ll begin at Milsons Point, heading through Wendy’s Secret Garden and Lavender Bay to explore a hidden location, before wandering through Kirribilli Village, lined with blooming Jacarandas. Our next stop will be the iconic McDougall Street and Milson Park — Sydney’s most photographed Jacaranda spot. From there, we’ll follow quiet trails to Forsyth Park, another hidden gem full of purple blooms, before wrapping up near North Sydney — just in time for drinks at the Greenwood Hotel, or you can take the Metro or train back home. * **Gratuity:** Free **Important - Please Read:** * **What to Bring:** Wear comfy shoes, bring **hydration (1 litre, we have many refills along the way), snacks/lunch,** sunscreen, a hat, and weather protection. * **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) * **Get involved** – You're welcome to send the host feedback or let us know if you’d like to lead such walks. **Connect with Us:** * Facebook Private Group: [https://www.facebook.com/groups/ozoutdoors](https://www.facebook.com/groups/ozoutdoors) * Instagram: [https://instagram.com/ozoutdoors.syd](https://instagram.com/ozoutdoors.syd)
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