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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

Middle Cove Mangroves, Middle Cove

Middle Cove Mangroves, Middle Cove

Sat, Jun 13, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

Today's HIKEFit program explores parts of Castle Cove… Although it feels like a flat walk, there are some good ups and downs. You can complete 8 km or the full 11 km and get around 400m in elevation. We will start at the steps heading into Scotts Creek. After passing the creek, we find a management for about 500 metres. Then we are back into the bush heading to FigTree Cove via the North Arm walking track. Find our more at [HIKEFit.au](https://sterlingfitness.com.au/hike-training-in-sydney/) #HIKEFit #HIKINGINSYDNEY #HIKESYDNEY #SYDNEYHIKING

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1 attendee
Whale Hike! Cronulla, Captain Cook's Landing, Kamay Nat'l Park to a GREAT PUB!!!

Whale Hike! Cronulla, Captain Cook's Landing, Kamay Nat'l Park to a GREAT PUB!!!

Sat, Jun 20, 11:38 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**Cronulla, Kurnell, and "[Cook at Kurnell"](https://www.cookatkurnell.com.au/) (pub)** is part of Sydney not many have been to. Trust me, this hike is one you'll want to do. With the whales coming north, the cliff faces are the perfect viewing point(s) in June. If you've come on our Macmasters Beach to Killcare Beach & **Hardy’s Hideaway Pub** it’s in a similar spirit. If you missed it? Here’s your second chance at a memorable session... **Cronulla Beach to Kurnell / Kamay Botany National Park to the site of Captain Cook’s Landing to… “Cook at Kurnell”** for food and drinks. It's a 14.86kms hike. Imagine this: *“Hey Davo. Grandpa died. He left us the beach property. Let’s put some booze and beer kegs into his VW van and make a service window. And let’s empty out his trailer and put a kitchen in it. We’ll add picnic tables, umbrellas, live music and open a beach bar called Cook at Kurnell.”* Who knows if that's true. But **Cook at Kurnell** is exactly that kind of joint… **I’ve been to the bar – love it. I’ve done an hour hike to Kurnell – love it. And I love the Tozzi family who owns it.** **So? Grab my arm, and join me.** **[JOIN OUR WHATSAPP GROUP HERE](https://chat.whatsapp.com/FZiGipXk9kY5mqLh49wGa2)**[.](https://chat.whatsapp.com/C2OLdpsxYQo3Y88VDZlUvI) Team, please stop here. After you hit attend, come back to the event page - click on the link, and join the whatsapp group. It's a must for this event. **THE DETAILS:** **Driving?** 950am Find free parking at Greenhills Outdoor Basketball Court. [MAP](https://www.google.com/maps/place/Greenhills+Outdoor+Basketball+Court/@-34.0410587,151.1619584,18.4z/data=!4m6!3m5!1s0x6b12b7efeb0b90db:0xa5dae16610e8dcb7!8m2!3d-34.0409667!4d151.1622065!16s%2Fg%2F11k0sl0ngh?entry=ttu&g_ep=EgoyMDI1MDUyMS4wIKXMDSoASAFQAw%3D%3D) 951am to 10am You'll see those that took the train arrive from the bus. **1010am Hike starts!!!** **Public Transport?** 987 bus leaves from Cronulla Station at 945am, dropping at our hike start at 951am. **Do NOT miss that bus.** I'll meet you all at Cronulla Station at 940am. Find me. Trains arrive every 10minutes. Coffee and bathrooms are right there. Bus to the starting point. **1010am Hike Starts!** **After the pub finish, 987 bus is right by Cook @ Kurnell that drops:** a) Close to the basketball courts (for drivers); b) Drops us train riders back at Cronulla Station. Easy! Winding through **Cronulla dunes** **and onto the beach** we’ll elevate into **Kamay Botany National Park**… I’m not going to write a lot about it. It’s absolutely beautiful. Cliffs. Ocean. Views. It’s 10/10 (look at the pics from the last hike). It’s medium-hard with some uphill bits but nothing crazy difficult. 14.5kms so be fit, healthy, and bring some good energy and thirst for a beer or two. See you for an epic hike and pub! 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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6 attendees
Killarney Hills, Killarney

Killarney Hills, Killarney

Fri, Jun 5, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

We are doing the Iconic Killarney Hills. I hope you can make it. We will meet on Cook Street in Forestville. This is a long hike covering mountain bike tracks, and incorporating lots of steps and undulations. We get a great break on the water at the halfway mark; this hike is all within the Garigal National Park. Poles are recommended. The first part of this hike is just under 10KM, but there is always an extension if you are tempted. Find our more at [HIKEFit.au](https://sterlingfitness.com.au/hike-training-in-sydney/) #HIKEFit #HIKINGINSYDNEY #HIKESYDNEY #SYDNEYHIKING

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1 attendee
Australia WCup Opener! $7 Pints. Hike first!!!

Australia WCup Opener! $7 Pints. Hike first!!!

Sat, Jun 13, 11:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

Australia v Turkey. World Cup 2026, 2pm kick off. Let's drink. Laugh. Get filthy at Sydney's best sports bar (my local, Sporting Globe by 4 Pines) on the water ($7 Pints / 20% off all food, drinks with my VIP card). But first? We hike... **THE DETAILS.** Coming soon. Get in quick. This one will fill out - the whole bar will be booked like New Year's Eve. $10. Newbie hikers - gotta come on some hikes before joining special days like this one. We did this for Women's World Cup a few years back and Sporting Globe was fucking wild - this will be even better! **[IF YOU CLICK ATTEND, NEXT STEP IS JOIN THE WHATSAPP GROUP HERE.](https://chat.whatsapp.com/Dd3vOoCoOmxIpVxiLIhbCE)** ***AN AD FROM THE MARKETING DEPARTMENT.*** ***JUNE!!! Here's what's on in We Hike... to the Bar:*** *Monday, 1 June - [VIVID WALK, DRONE SHOW, 50% OFF WINGS, DRINKS!](https://www.meetup.com/hikewalktothebar/events/314952719/)* *Saturday, 6 June – [Macmasters Beach to Killcare, Hardy’s Hideaway. My favourite hike!!!](https://www.meetup.com/hikewalktothebar/events/314873258/)* *Sunday, 7 June – [Woy Woy to Patonga Beach / The Boathouse](https://www.meetup.com/hikewalktothebar/events/314873444/) – such a pretty session.* *Saturday, 13 June – [Royal National Park Figure 8 Pool!](https://www.meetup.com/hikewalktothebar/events/314972877/) This is a 10/10 hike.* *Sunday, 14 June – [We Hike… to the Australia v Turkey World Cup Opener!!!](https://www.meetup.com/hikewalktothebar/events/314175185/)* *Saturday, 20 June – [MJ’s Bday & Winter Pub Crawl!](https://www.meetup.com/hikewalktothebar/events/314958235/)* **THE HIKE.** I'll pick a Sydney Harbour hike / something close. Perhaps a coastal hike as the whales are coming north... 930am start, and let's have our asses in bar seats by 130pm. *Apologies in advance - if you haven't come on too many hikes and somebody else has, they might take your seat for an event like this.* Funnnnnnnn, fun. See you soon in June! MJ

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50 attendees
Secret trail Hunt, Lindfield

Secret trail Hunt, Lindfield

Sun, Jun 7, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

We will warm up on a lovely meandering trail from Lindfield Oval down to a wider management trail where we set a fast pace. Today we will cross Barrie Creek and take a wandering trail before climbing to Barrie St. If the weather is fair, we will return to the creek by a foot pad so that we really get the flavour of the casuarina forest through which we are walking. The views from near the water are very pretty, so keep your camera ready. I recommend you wear long pants for this one. Find our more at [HIKEFit.au](https://sterlingfitness.com.au/hike-training-in-sydney/) #HIKEFit #HIKINGINSYDNEY #HIKESYDNEY #SYDNEYHIKING

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1 attendee
Friday Nite Hike! Stunning 7kms Taronga Zoo to Balmoral Beach Hike! Beer too!

Friday Nite Hike! Stunning 7kms Taronga Zoo to Balmoral Beach Hike! Beer too!

Fri, Jun 26, 7:30 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

Nite hikes are super fun, and we've done a couple so let's do it again! We'll 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/EjKueK9RY6DJzKL6roTpGm) 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, just for safety reasons. Get to KMart... they are $10. Your mobile phone's flashlight will be fine too.)*** 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 530pm. 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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1 attendee
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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.