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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
HIKEFit_EXpress - Summit Sessions

HIKEFit_EXpress - Summit Sessions

Tue, Oct 13, 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
HIKEtoberfest! SUNSET @ MIDDLE HARBOUR - THE AUSTRIAN CLUB! Octoberfest!

HIKEtoberfest! SUNSET @ MIDDLE HARBOUR - THE AUSTRIAN CLUB! Octoberfest!

Thu, Oct 22, 5:36 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**"MJ, how in the fahk did you find this schnitzel place?"** **Just wait. I know you're gonna say those exact words when we walk through the doors...** **I love this short yet challenging hike(s). I love this restaurant. It is October, so let's celebrate with a sunset hike to the best European schnitzel in Sydney!** **THE HIKING – EATING – DRINKING PLAN:** First, the bus. The **172x leaves Wynyard Stand A (corner of Carrington Street and Margaret Street) at 436pm.** Tell your boss you've gotta "drop tools" at 415pm, and meet us there. If you miss this bus? You miss the event (or an expensive Uber to catch up). The bus drops at Seaforth Oval 513pm... quick change / bathroom for those who need it, and off we hike at 530pm (drivers read below). **Middle Harbour Hiking 4kms.** Middle Harbour is stunning, and **The Bluff Lookout** is the prize at the top that’s not to be missed. When we leave Seaforth Oval, you will not believe how Mother Nature has carved this trail and caves so close to suburbia (and **The Austrian Club**). It’s the perfect start to build up some hunger Octoberfest. The **Bluff Lookout Sunset** is the finale, and it's 300m away from our Austrian destination. Yet be aware – sure it’s close to Sydney’s CBD – but this trail has ascent and will be a bit challenging (*from Harbour level to 153metres - you'll earn your beer*). Please join our whatsapp group **[HERE](https://chat.whatsapp.com/G6Xa9ByXTlu1LHO5ckSZWV) \- all members for this hike must join\.** **The Austrian Club.** Wait ‘til you see this schnitzel haus – you’ll feel like you’re in rural Austria. It’s so authentic, so friendly, and so delicious. We found this delightful joint quite a while ago, and no shit a week later it appeared in **[GOOD FOOD Sydney Morning Herald, and they loved it](https://www.smh.com.au/goodfood/sydney-eating-out/this-raucously-cosy-club-serving-schnitzels-and-schnapps-is-still-going-strong-after-45-years-20250303-p5lgkp.html)**. Their **[MENU IS HERE](https://www.austrianclubrestaurant.com/menu/menu.pdf)**. The local government donated land to the Austrian community, and they built an authentic home that's not to be missed. When we leave, we'll jump back on the bus - no doubt some will share an Uber too. The bus is a little tricky, but I've got it worked out / will explain on the nite. **The LOGISTICS:** a) *Be on time. Be safe. Be fit for the ascent.* b) **172x Bus** drops right at Seaforth Oval, our meeting point. There's parking there too, but smart drivers would park at The Austrian Club and $10 Uber (or **141 Bus** down) to our starting point then hike to their car. c) Cancels (day before or on the day) / no shows. Nope. Don’t do it. The Austrian Club has my credit card for the reso, and the workers are volunteers – if you RSVP “Attend” then show up. d) **$10 for this one. Cash or PayID.** e) Bring good energy. Bring mates or dates. Chat. And laughs. Let's have some grand fun in Mother Nature. g) Again, please join our whatsapp group **[HERE](https://chat.whatsapp.com/KTSf8JzeVAPLs6c5FeMFx3)**, so we can all find the starting point. See you for a beautiful and fun nite-hike! MJ 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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4 attendees
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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65 attendees
"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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12 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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45 attendees
430kMonthly events
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60mMembers
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4.5App store rating
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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.