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Challenging Hikes Sydney

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HIKEFit_EXpress - Summit Sessions

HIKEFit_EXpress - Summit Sessions

Tue, Oct 27, 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
"WOW" Session: 12kms Flat Rock Gully to Spit Bridge! "Cheers" @ Pub to Finish!

"WOW" Session: 12kms Flat Rock Gully to Spit Bridge! "Cheers" @ Pub to Finish!

Fri, Oct 30, 11:15 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

Over 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.* **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).

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38 attendees
2026 WHALE TRAIL: Narrabeen to "Sunday Sippers" at Bilgola Beach!!!

2026 WHALE TRAIL: Narrabeen to "Sunday Sippers" at Bilgola Beach!!!

Sun, Oct 25, 12:30 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

*Okay team... Mother Nature and her rain said "NO" today yet we still had a laugh, drink, and another drink. So? We try again, as this hike / bar is too good to miss out on...* We looooove our Sydney trails that treat us to **secret beaches**. We love finishing our events at **secret bars you’d never find**! What about an event… a **stunning hike that finishes at a** **secret beach bar** **with a band** that starts at 4pm bringing us right into a glorious sunset? On August 30, we did this hike but from the other way… Palm Beach down to Bilgola, and let me say this… **SUNDAY SIPPERS AT BILGOLA SLSC IS ONE OF THE COOLEST LITTLE BARS IN ALL OF SYDNEY!!!** It’s RIGHT on the beach. It’s only open once a month. **This bar is unforgettable (burger, beer pic is from Bilgola SLSC). Don’t miss this HIKE!** **THE HIKE. Narrabeen Beach to Bilgola Beach - 13.5kms.** We'll meet at the bus stop in North Narrabeen ([CLICK HERE for exact point where 199 bus drops)](https://www.google.com/maps/place/Northern+Beaches+Community+College,+Pittwater+Rd/@-33.7022113,151.2985563,18.82z/data=!4m15!1m8!3m7!1s0x6b0d550541a46f25:0x5017d681632c2f0!2sNarrabeen+NSW+2101!3b1!8m2!3d-33.7222735!4d151.2984024!16zL20vMDM4eDgz!3m5!1s0x6b0d54e1517e958b:0x284ff3157c081ca9!8m2!3d-33.702148!4d151.298203!16s%2Fg%2F11gzdz06t?entry=ttu&g_ep=EgoyMDI2MDgyNi4wIKXMDSoASAFQAw%3D%3D) \- we'll discuss it in the [whatsapp chat too](https://chat.whatsapp.com/FXMgLB7M7Rp7jH6ol6nf8g)). The 199 bus stop is there, then we'll cross the road and check out the rockpool then head into **Narrabeen Headland** which gives the most spectacular views south. Onward we go to **Turimetta Beach** (10/10 breathtaking) and **Lookout**… to the **Turimetta Headland Reserve, Warriewood Lookout & Blowhole**, **Warriewood Beach (again gorgeous), then to Mona Vale Beach (voted 6th best in the world, Conde Naste)**… North of that? **Basin Beach. Bungan Beach**.... these two are truly beautiful. We'll climb out of Bungan then head to **Newport Beach...** around the headland is **Bilgola Beach**, and we'll descend down some lovely stairs right onto the sand where **Bilgola SLSC** lies. *(Edit: Apologies in advance. This hike will get FULL. I have to let those that have been on many hikes in on seniority.)* **13.5kms in total**. Beach walk. Inclines. And all the rest. Fitness required for this one. The **B1 bus / 199 bus are our friends all day to start, get home, and even provide some outs if you want to stop hiking and meet us at the pub.** If you parked your car at the start (there is free parking but DIY research) it's super easy to bus back south. Post-pub the 199 bus is literally up the stairs from Bilgola and runs every 10minutes. We'll arrive at the pub about 320pm (330pm opens)... I get it. It's Sunday. If you want to leave? That's okay. One drink. Stay longer? All options are open... See you for one of my favourite Sydney hikes and definitely my favourite (new) secret bar! MJ ***AN AD FROM THE MARKETING DEPARTMENT.*** ***September!!! Here's what's on in We Hike... to the Bar:*** 5th Saturday… [Macmasters Beach to Killcare to Hardy’s Hideaway](https://www.meetup.com/hikewalktothebar/events/316347936/) 6th Sunday… [Blue Gum Loop Hornsby & New Quarry](https://www.meetup.com/hikewalktothebar/events/316348293/) 12th [A Hike, Sunset & ABBA](https://www.meetup.com/hikewalktothebar/events/316365727/) 13th [SPIT BRIDGE TO MOSMAN ROWERS!](https://www.meetup.com/hikewalktothebar/events/316413157/) 17th Byron Bay – 21st Byron Bay 26th Saturday… Cronulla to Cook @ Kurnell (Coming Soon) 27th Sunday… [Secret Beaches to Sunday Sippers at Bilgola Beach SLSC (my new, fav hike and bar of 2026)](https://www.meetup.com/hikewalktothebar/events/316348531/) **______________________________________________________** **THE DETAILS.** **WHATSAPP.** You’re not 100% confirmed until you’re in the whatsapp group. Join it 'cause we love it, and 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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42 attendees
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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13 attendees
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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14 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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3 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.