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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

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
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
St Ives Hills, St Ives

St Ives Hills, St Ives

Fri, Jun 12, 9:00 PM
From Sterling Fitness Hiking Adventures
4.9

HIKEFit will meet at the car park of Acron Oval. We will walk down a steep management trail meandering our way through the National park. After a while we will see the cascades, then we will traverse up and down through different trails, to keep our heart rate and legs working. Today's hike is testing you on hills, and steep declines. Poles are highly recommended. 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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51 attendees
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
Secret trail Hunt, Lindfield

Secret trail Hunt, Lindfield

Sun, May 31, 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
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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.