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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
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

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).

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30 attendees
HIKEFit_EXpress - Summit Sessions

HIKEFit_EXpress - Summit Sessions

Tue, Sep 29, 8:30 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
Long Wknd Nite Hike. Lovely 7kms Taronga Zoo to Balmoral Beach Hike! Beer too!

Long Wknd Nite Hike. Lovely 7kms Taronga Zoo to Balmoral Beach Hike! Beer too!

Fri, Oct 2, 7:30 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

A few months back we hiked Coogee to Bondi at nite, then this hike - it was really, really cool. Beer before... and (meal) after. Love it - it's a different kind of energy when you hike in the evening. Just posting this on Wednesday - let's see if we can get 8-10 hikers for Friday :) High of 21 degrees too - perfect! Let's hike post-sunset Taronga Zoo towards Balmoral Beach while talking shit and licking our beautiful city then head up to the lovely Buena Hotel in Mosman (one of my favourite Lower North Shore pubs) for a great pub meal. ***Taronga to Balmoral***. It’s an Aussie fahkin' beauty of a due to its diversity… Of course the ***ferry ride from CQuay to Taronga (ferry leaves at 545pm - be early*** is amazing, and the first stint of the walk transports you to another part of Australia – it’s a rainforest start to ***Bradley’s Head*** with perfect views of ***Sydney Opera House / Harbour Bridge***. Turning the corner we’ll stop at a secluded beach then carry on to ***Taylor’s Bay*** – the greenery / plant life there will amaze all. [NOTE: YOU MUST JOIN OUR WHATSAPP GROUP FOR THIS EVENT HERE.](https://chat.whatsapp.com/DFaK1MR9dKB8F3bqWCoint) From there the walk heads to ***Chowder Bay***, one of the coolest little beaches that not many Sydneysiders know of. There’s a café / bathroom stop there, then up the only real incline to ***George’s Head***: a historic military spot with the most picture perfect view from Manly to the CBD. We head back into the bush for a 15min walk to the ***Balmoral Stairs*** that will guide us down to Balmoral Beach. ***(SAFETY NOTE: I'm recommending a head lamp if you don't have one, but "I'll just use my mobile phone's light" was sufficient last time. For safety get to KMart... they are $10)*** Post-food / drinks you have many transport options from Balmoral Beach / The Buena to get back home or to Wynyard. I'll guide you. Oh, stay tuned for location to meet at 430pm. I'll be at a pub from 5pm around Circular Quay warming up... join from 5pm-530pm then we'll walk to the ferry wharf as a team. See you for a fun Friday session! MJ **_____________________________________________________** **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.** $10 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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17 attendees
🌸CQ🌸Harbour Bridge🌸Harbourside walk to Balmoral Beach🌸

🌸CQ🌸Harbour Bridge🌸Harbourside walk to Balmoral Beach🌸

Thu, Oct 1, 12:15 AM
From Aussie Explorers
4.8

MEETING: Circular Quay Wharf 2 🌸✈️🌸 TIME: 10:15 🌸⏰🌸 DETAILS: This walk is nothing short of spectacular! We head from Circular Quay via The Rocks over the Harbour Bridge, via Bradley’s Head, Harbourside Beaches, Taylors Cove, Middle Head, views the entire way! 🌸⛱🌸 LUNCH: Chowder Bay, Harbourside 🌸🍽🌸 COST:💲5️⃣ cash gratuity or (donation)for this walk.💵 🌸💲🌸 DISTANCE: 1️⃣4️⃣kms 🌸🦋🌸 THIS WALK IS GRADED AS: Stunning! Ups, downs, tracks, stairs…. All worth it 🌸☀️🌸 GET OUT POINTS: a Bus or ferry is always just around the corner 🌸🚦🌸 TRANSPORT: Bus/ ferry from Balmoral back to CQ… many other options to other destinations 🌸✈️🌸 GENERAL HOUSEKEEPING: 🌸💃🌸 IF YOU WOULD LIKE TO BRING A FRIEND PLEASE MESSAGE ME, unfortunately only the 2 legged kind, and not the 4 legged kind are included. 🌸🥰🌸 I am always open to suggestions if there is a destination/hike/walk you’d like to do…just message me 🌸 👣🌸 A heads up for newcomers and first timers. Our walking group is a fabulous Melting Pot of cultures, backgrounds, professions and life experiences. We love our Walks. We are INCLUSIVE OF EVERYONE………if you’re: kind, nice, fun, polite and respectful. 🌸😘🌸 On that note…. In recent times my walks are at capacity, which I’m capping at 40. Regulars, regardless of numbers are always welcome….just PM me if you’re on a waitlist. 🌸♥️🌸 We walk at a medium pace of 4kms per hour, stopping for breaks and to take in the views. It is a reasonable expectation that the group stays together. It is your responsibility to stay in line of sight. If you cannot walk at this pace, I will let you know of the next get out point. This is not negotiable. 🌸🐌🌸 As this is a walking group, bikes, ebikes, scooters, escooters, and pogo sticks are not compatible or welcome. 🌸👣🌸 Grading for my walks:
Easy: Mainly flat, suburban, loads of get out points, up to 14kms.
Easy-Medium: some stairs, a few uneven surfaces, up to 15kms.
Medium: Stairs, rocks, coastal beaches/sand, ups, downs, get out points limited, up to 17kms
Medium-Hard: uneven surfaces, need to take extreme care and be hike fit. Few get out points. Tracks, uneven surfaces, steep inclinations and limited resources. 🌸👯‍♀️🌸 WALKING GUIDELINES & RESPONSIBILITIES: 🌸✍️🌸 Carry sufficient food and water (2 litres) for the expected conditions of the walk. Pls don’t separate from the group, unless you let someone know, preferably me. The waitlist is completely discretionary….reliable regulars will ALWAYS be included. 🆗……….If you are a no show, you will not be welcome to join a future walk with me. (It’s a courtesy kind of thing). If people are on the waitlist, it is also very inconsiderate. Marking yourself as “Not Going” within 2 hours of departure does not allow reasonable time to notify anyone on the waitlist. 🌸🙅‍♀️🌸 On the odd occasion, the walk may change from the schedule, due to weather, unforeseen track obstacles OR emergency situations. 🌸🤞🌸 Please make sure your conversation is always courteous to other group members. 🌸😍🌸 PS…. IF YOUR ID PIC IS OF A COFFEE CUP, YOUR DOG OR CAT, A VIEW, and not a picture of you…You’ll stay waitlisted. 🌸❌🌸 SAFETY WARNING: Please stay away from cliff edges and be very careful when walking on wet and slippery rocks and surfaces. Stay within sight of the group at all times. 🌸🔴🟢⚫️🟠🔵🟡🟣🟤🌸 DISCLAIMER: Your health and safety is our priority, 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 🌸☀️🌸 HAPPY WALKING 🍃🌸🌿🌸🌿🌸🍃 xxLisa

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17 attendees
🌅 Sydney Harbour Sunset Walk: Bridge, Bays & Botanic Gardens (~15km)

🌅 Sydney Harbour Sunset Walk: Bridge, Bays & Botanic Gardens (~15km)

Sun, Oct 4, 5:00 AM
From OZ Outdoors
4.8

Join us for around \~15-kilometre **sunset exploration of stunning Sydney harbour - with our evening walks group!** This moderately paced walk offers incredible scenery, historical sites, and beautiful evening vibes. Good fitness is recommended as we will maintain a steady pace through a variety of urban terrains. **Before you RSVP, be sure to read the following:** * [If you have TrekMeet, please RSVP by clicking on this link.](https://trekmeet.com/event/56c53938-b40c-46e0-b032-07cd54f343f4?from=9xOdy7cJLyewPf1Nkak5XAkdmtI2) * **Difficulty and Terrain:** Easy to Moderate (for regular hikers). Expect a diverse mix of stairs (many!), paved streets, some rougher bush sections, and parklands. * **Start:** 4:00 PM sharp at Milsons Point Station (Ennis Road / Kirribilli side). Please arrive 10 minutes early. Finish: Central Station. (Plenty of public transport exit options along the way if needed). * **Route:** We will start by walking south across the iconic Sydney Harbour Bridge, continuing down through the historic Rocks district and past the Opera House. We'll then weave through the Royal Botanic Gardens to catch the sunset views, head down to the Woolloomooloo Finger Wharf, and sweep around the foreshore to Rushcutters Bay. From there, we will navigate back through the surrounding inner-city streets to finish up at Central Station, where we can grab an optional group dinner at Don Giovanni Pizza. https://www.dongiovannipizzabar.com.au/menu * **What to bring:** Comfortable sneakers (uneven terrain possible in some areas), charged phone or torch/headlamp for dark sections (after 5.30 PM), water (refills available), and weather-appropriate clothing. * **Gratuity:** Free, just give us a [follow on our](https://www.instagram.com/ozoutdoors.syd) or [trekmeet](https://www.instagram.com/trekmeet) social. **Important - Please Read:** * **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 on Instagram:** [https://instagram.com/ozoutdoors.syd](https://instagram.com/ozoutdoors.syd) * **LinkedIn (Manish):** [https://linkedin.com/in/manishpm/](https://linkedin.com/in/manishpm/)

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16 attendees
430kMonthly events
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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.