Skip to content

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
Hornsby Blue Gum walk

Hornsby Blue Gum walk

Thu, Oct 8, 11:00 PM
From Boots and Blisters

🥾 What to Expect on the Hike 📍 Meeting Point We’ll meet outside Hornsby Station and then walk together to the start of the Blue Gum Walk, which is about a 10-minute walk from the station, near Hornsby Quarry. 🥾 The Walk The Blue Gum Walk is approximately 5 km, with some uphill and downhill sections. It’s a relaxed hike, so we’ll take our time and enjoy the surroundings. 🌿 What You Might See Depending on the day, we may spot: 🦎 Water dragons 🐦 Different types of birds 🐟 Fish in the pond 🌳 Beautiful bushland and scenery 🎒 What to Bring 💧 A water bottle — definitely recommended 🍎 Fruit or protein bars if you’d like a snack 🥾 Comfortable walking/hiking shoes ☀️ Sunscreen and a hat are also a good idea 👋 How to Find the Group We’ll meet outside Hornsby Station before heading off together. I’ll be there at the meeting point so everyone can easily find the group. Most importantly, come ready to enjoy a relaxed walk, meet some new people and have a good time! 🌿🥾😊

  • Photo of the user
  • Photo of the user
2 attendees
BEST HIKE IN 'Straya? Blue Mountains GRAND CANYON HIKE. Pub Lunch & Beer.

BEST HIKE IN 'Straya? Blue Mountains GRAND CANYON HIKE. Pub Lunch & Beer.

Fri, Oct 9, 10:51 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**(EDIT: We need a few drivers for this one! If you can drive - you'll skip the waitlist, and you're in! Just send me a note - 0439 635 699) :)** From TIMEOUT Magazine: *"One breathtaking bushwalk claimed the crown as the nation’s favourite. The gold medal went to the **Grand Canyon Track** – a challenging yet short hike through the lush rainforest of the World Heritage-listed Blue Mountains National Park. The 6.3-kilometre circuit passes gently cascading waterfalls, giant ferns and moss-covered rocky overhangs that look straight out of a fairy tale."* Yup. A fahkin' fairy tale that ends with a beer and lunch. (Moved this to October as more sunlight will make for a better day!) **THE HIKE.** It's a 6.3kms loop hike. NSW Parks estimates 3-4 hours, which means this hike is medium in difficulty (430m of altitude gain is a lot of steps, but it's not that bad when you're there). It's absolutely beautiful - waterfalls, greenery, views, and more. It's like somehow Mother Nature carved out this perfect crevasse - hiking it has you exiting civilisation into Jurassic Park-esque world. *Fitness matters here, but we will be hiking at a relaxed pace so we enjoy our surroundings.* Last time I had a video of the hike here. I deleted it. Just come. At Step #1 where we view Evans Lookout, it's truly a "Woowowowowowow" type start. It only gets better from there. **THE TRANSPORTATION.** A train arrives at Blackheath Station at 951am. Let's meet at the pub across the road. There's parking and toilets there. However, let's try to get enough drivers for this one. The train arrives in Penrith at 827am. **[Perhaps drivers pick us public transporters there? Let's discuss this all in the whatsapp chat that you must join on this hike!](https://chat.whatsapp.com/KngCa1lMtdUEAoSy6zXuGP)** **LUNCH.** "[Spikes Bistro](https://www.facebook.com/p/Spikes-Bistro-Blackheath-61574548437651/)" (where all the locals are going these days) is now a family run joint at the golf course with GREAT food. I'll make a reservation right on the same balcony we had last time! It's a perfect ending to The Grand Canyon, and the family is thankful to have our business. Let's support the locals who support us. **ANOTHER HIKE.** We'll have cars. Shall we do another short hike? I'm open. Charles Darwin Trek is newly open, and it's an easy one with top, top views of Wentworth Falls. Valley of the Waters? Another 10/10 waterfall hike. Or no doubt you'll be able to get a lift to Blackheath Station if you need to get home. **THE DRIVERS.** We need some drivers for this one. If you drive each passenger you take from will chip in some cash - I'll see to it. We looooove you drivers! **THE LOGISTICS.** a) Gratuity $15 Cash or PayID on the day. b) Let's try to start hiking by 1030am 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. This will be a hike you won't forget - I can't wait to see the "Holy shit, WOW" look on all of our faces! See you soon. MJ 0439 635 699 **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).

  • Photo of the user
  • Photo of the user
  • Photo of the user
26 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)!*

  • Photo of the user
  • Photo of the user
  • Photo of the user
62 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. **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.

  • Photo of the user
  • Photo of the user
  • Photo of the user
37 attendees
12kms Flat Rock Gully to Spit Bridge! Sunday Roast "Cheers" @ Pub to Finish!

12kms Flat Rock Gully to Spit Bridge! Sunday Roast "Cheers" @ Pub to Finish!

Sat, Oct 10, 10:45 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

Wow. A hike in the middle of Sydney that we haven't done! And this session looks delightful. Sheez as I'm looking at the map I can't believe this green trail / river zigs and zags all the way down to Spit Bridge through lush neighbourhoods... this looks like a really cool hike / walk!!! We'll finish at the pub to "Cheers" at the end of our weekend. **THE HIKE.** I won't write much, as this is a newbie to me too (I'll do a trial run on my own this week), and the map (pic) doesn't do it justice as there's so much greenery along this journey. Let's meet **Artarmon Station** (on the platform) then **Artarmon Reserve** turns into **Flat Rock Creek and the Flat Rock Gully Track**... and this twists and turns all the way down to **Middle Harbour**! Bit of a neighbourhood walk (no doubt amazing homes) leads to **Primose Park, Brightmore Reserve** right on the water... down to the last 3kms which is hugging the water down at **Middle Harbour to Spit Bridge** \- definitely one of the nicest places in all of Sydney\. From there? Pub. Of course. Always. Let's cheers to our 12kms journey. Minsky's in Cremorne has been a pretty decent spot for us in the past with nice food. A reservation has been made, and their $27 Sunday Roast looks pretty damn good.. This hike / walk is mostly downhill with some minor ups / downs... but it looks like a pretty relaxed 12kms. Perfect for a **Sunday Session starting at 945am.** *[TEAM. UNSURE WHY THIS IS A TOUGH ONE. AFTER YOU HIT ATTEND. COME BACK. HERE. SEE THESE CAPS AND HOW IT'S UNDERLINED? THAT IS A LINK TO OUR WHATSAPP GROUP. YOU MUST JOIN THE WHATSAPP GROUP TO COME ON THIS HIKE!](https://chat.whatsapp.com/GjaW0lTW45C5BdIpPn9SBc) (All said with a smile and friendly nudge)* Drivers, please DIY about Artarmon parking, and we'll get ya back there via bus from Spit Bridge / the pub on the day. See you there! MJ **THE LOGISTICS.** a) Gratuity $15 Cash or PayID on the day. b) Let's try to start hiking by 10am 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).

  • Photo of the user
  • Photo of the user
  • Photo of the user
15 attendees
430kMonthly events
calendar icon
60mMembers
people1 icon
4.5App store rating
appStore icon
200kGroups
people2 icon

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.