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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

Manly Dam Circuit, Seaforth

Manly Dam Circuit, Seaforth

Fri, May 29, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

We traverse down to the Dam, cross a bridge and await hiking surprises including the Mermaid Pools. Depending upon the day, your Hike Coach will find an interesting and challenging path for you back to the cars. Find our more at [HIKEFit.au](https://sterlingfitness.com.au/hike-training-in-sydney/) #HIKEFit #HIKINGINSYDNEY #HIKESYDNEY #SYDNEYHIKING

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1 attendee
2026 WHALE TRAIL: Long Reef to Newport, a Coastal Stunner!

2026 WHALE TRAIL: Long Reef to Newport, a Coastal Stunner!

Fri, May 29, 11:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

This session is easily in my Top 5 Hikes in Sydney... the bush, the beaches, the neighbourhoods, and a lush pub to finish. And? It's a star in our **2026 WHALE TRAIL** series as we smash the coast spotting whales along the way. There's something very fahkin' special about those Northern Beaches, and **Long Reef Headland to Newport is a 10/10 journey showcasting the best of the best**! **THE HIKE. LONG REEF HEADLAND TO THE NEWPORT - 15kms.** We start at **Long Reef Headland**… one of *the most stunning sections of our Sydney Coastline*, from Palm Beach all the way down to The Royal National Park. We meet there in the grass by **Long Reef Surf Life Saving Club.** **Long Reef** is 240million years old, and the views are unforgettable. We bend around **Long Reef Golf Course** and exit to a cute little beach walk at **Fisherman’s Beach** (we saw sting rays galore there last time) which finishes at **Collaroy Rockpools**… leading to **Collaroy Beach**. Admittedly, the stretch of Narrabeen Beach is either torture on the legs in the sand or a boring-as-hell street walk, so we'll jump on a 5min bus (trust me, this works) to skip it. Hiking continues at **Narrabeen Headland** and gives the most stunning views south so you'll see it all. Onward we go to **Turimetta Beach** (10/10 stunning) 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)**… **[(QUICKLY... YOU MUST JOIN OUR WHATSAPP GROUP HERE AFTER YOU HIT ATTEND HERE ON MEETUP)](https://chat.whatsapp.com/HcJO5KPN8aZ8eX0CurXW7L)** North of that? **Basin Beach. Bungan Beach**.... these two are absolutely stunning. Let's explore, then we'll make a left into Newport to easily one of the best bars in all of Sydney - **The Newport**. If you haven't been, you're going to be floored. If you have, it's probably why you're signing up to this hike! **15kms 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) it's super easy to bus back south. Post-pub the 199 bus is literally out the front door running every 10minutes. **THE STARTING POINT.** Coming from North or South? B1 bus gets you close, but it’s an easy transfer to the 199 bus that drops you at the **Collaroy at Pittwater Rd before Hay St stop**. Cross the road there (be careful, look at pic for the stairwell), take the trail down, and the grassy bit is our meeting point (please see pics below). It’s a little tricky, but you’ll find it. Drivers, there’s freebie parking around that area – DIY research please. See you for one of my favourite Sydney hikes! MJ \| **THE 2026 WHALE TRAIL** \| **KMs** \| \| La Perouse Headland \| 11\.0 \| \| Figure 8 Pool \| 14\.0 \| \| Wattamolla\, Eagle Rock \| 14\.0 \| \| Bundeena to Wedding Cake Rock \| 17\.0 \| \| North Head Manly \| 12\.6 \| \| Malabar to Coogee \| 11\.2 \| \| Coogee Watson's Bay \| 16\.6 \| \| Long Reef to Newport \| 15\.2 \| \| Cronulla to Kurnell \| 14\.9 \| \| Dee Why to Manly \| 10\.9 \| \| Macmaster's to Killcare \| 13\.5 \| \| Patonga to Pearl Beach\, Palm Beach \| 14\.0 \| \| **12 HIKES THAT TOTAL** \| **165KMs** \| **______________________________________________________** **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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24 attendees
Morgan Eight, Belrose

Morgan Eight, Belrose

Sat, May 30, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

You may not find the street number easily, it's about 950M from the Forest Way turnoff. Please look for fellow hikers' cars. We've been out on this trail several times now and it has everything, a management trail to warm up, some hills to raise the heart rate, a decent length to test your endurance, bike trails paths to entertain you and views to die for, and it all takes place in the Garigal National Park. In total around 10 KM hike. Allow around 3hours for the Hike and stretching. Find our more at [HIKEFit.au](https://sterlingfitness.com.au/hike-training-in-sydney/) #HIKEFit #HIKINGINSYDNEY #HIKESYDNEY #SYDNEYHIKING

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1 attendee
Middle Cove Mangroves, Middle Cove

Middle Cove Mangroves, Middle Cove

Sun, Jun 7, 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
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)** **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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51 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
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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.