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Challenging Hikes Sydney

Find thrilling hiking adventures in Sydney

11kms Coogee to Malabar Headland Hike!!! Microbrew & Food Truck Finish!

11kms Coogee to Malabar Headland Hike!!! Microbrew & Food Truck Finish!

Sat, Aug 8, 11:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

**Beach to Beach to National Park Headland to Microwbrew & Food Truck?!?! Absolutely. Add whales!!!** **[Wow this hike is popular](https://www.meetup.com/hikewalktothebar/events/315610037/)**, and on weekends Malabar Headland is only open 2 Sundays a month so I'm adding a second one - this is it. Of course the Marrickville & Freshwater microwbrews are well known, but there are also a few down in Botany that we've not explored together. Let’s check it out for a cracker of a Sunday session. **THE HIKE. 11kms.** **Coogee Beach…** we all know it. It’s a beauty. We'll meet just by Coogee Pavilion at that huge chair in the grass - it's actually a sculpture called "The Impressionists' Seat"... hiking along beautiful Coogee Beach. South Coogee turns a bit more tranquil with gorgeous cliff views and crazy-beautiful homes. We’ll twist and turn to **Maroubra Rocks and Beach**… looooovely spots. The rockpool at Maroubra is one of the prettiest on the coast. To **Malabar Headland** we goooooooooo! I still haven't done it, and it looks a treat (it's only open the 2nd and 4th Sundays of each month). Around to **Malabar Beach** then a 1km neighbourhood walk to the bus, and Beer Fontaine is close (if you have to leave after the hike, that’s understandable – it’s Sunday after all). **Beer Fontaine** is a lovely little spot, and they always have a food truck out front. Who doesn’t love a beer and food truck meal post-hike! A perfect Sunday Session. The 309 bus is close by and drops at Redfern. **[If you join, please come back here and jump into our whatsapp group by clicking on this link. It's a must to come to our events. Thanks!](https://chat.whatsapp.com/CFG41svS1MDKucIORnBLv0)** See you soon! MJ **THE OTHER STUFF** a) **Be on time.** If you’re late? Catch up. Please don't call, message. Just catch up. b) **$10** Cash or PayID. c) **Fitness matters here.** Sure, the pubs sound great, but we are hiking in National Park. Be prepared. d) **Honour your RSVP.** No shows get banned from the group. **I put my credit card down for a reservation – your reservation.** e) Bring mates, dates, etc... f) **Go back. Read the event. And join the whatsapp group!** ***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? Awesome! Send me a note first please - let's chat about your hiking experience and fitness.

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17 attendees
CLUB ROSE BAY LUNCH to Watson's Bay! Delightful 10kms Hike!

CLUB ROSE BAY LUNCH to Watson's Bay! Delightful 10kms Hike!

Sat, Aug 8, 1:45 AM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

This weekend, I'll be in Bondi dog-housesitting the 3 Labradors, so here's a hike I can host to escape the chaos then return home to see ***who ate what, and how much does it cost!*** **Rose Bay to Watson's Bay is a 10kms classic...** the beaches, the neighbourhoods, and the trails. It's a relaxed journey with stunning views to Sydney Opera House... finishing with an unforgettable outlook to the opening of Sydney Harbour and whales migrating north! And if you like a Saturday lie in, this start time should soothe your sleepy soul. (NOTE: TEAM - I CANNOT STRESS THIS ENOUGH AS I'M BAFFLED AT HOW MANY HIKERS CANNOT FOLLOW DIRECTIONS - after you join this event on MeetUp, come back here and you[ ](https://chat.whatsapp.com/GFp2gE2Ol44E0WmoZrAFiZ)**[MUST join our WHATSAPP GROUP by clicking on this link!!!](https://chat.whatsapp.com/JpEIDnIb1G4At86eDPy1lL)**) **CLUB ROSE BAY!** This place is so, so cool ‘cause it used to be a rundown RSL you wouldn’t dare go into. Wait ‘til you see **[Club Rose Bay](https://merivale.com/venues/club-rose-bay/)** now… the Merivale design, the food is so good (normal pub prices too), the military history, the pickleball & basketball courts. It’s this homely-decadent pub… with top-notch perving. We need to get there at pre-noon ‘cause by 2pm, this place is PUMPING every weekend. Our timing for lunch and a beer is Noon ‘til 115pm… let’s enjoy a proper pub lunch then burn off the calories with a glorious journey. *NOTE: 1145am arrival is key. Let's get in at noon, grab some tables... and enjoy! PLEASE BRING ID TO SIGN IN.* **THE HIKE.** **Rose Bay to Watson’s Bay is 10kms** of Sydney Harbour in its glory… **Rose Bay, Milk Beach, Shark Beach, Parsley Bay Bridge,** and onto **Watson’s Bay** and perfect views of Sydney Harbour’s entrance at **South Head & Hornby Lighthouse**. It's an easy hike with very few up / downhills - a magical session through parks, neighbourhoods, beaches, and Sydney Harbour National Park. When we finish you can take the picturesque ferry ride back to Circular Quay… If you know our hikes, you know we always find these "WOW" type places for a drink and a bite. Club Rose Bay is that place, and this hike a real gem to hike off the calories. Oh, and if you're only keen on the hike - just be outside at 110pm, and we'll see you 5minutes after that! Jump in. Jump in Whatsapp, and we'll see you soon! 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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34 attendees
Berowra Creek - Source to Hawkbury - Redux

Berowra Creek - Source to Hawkbury - Redux

Sat, Aug 1, 10:20 PM
From Off Peaks Club
4.9

Redux - Your host took a bad step and had to drop out. So we are starting again This idea is a series of hikes to explore Berowra Creek - its history and and its current vistas. This would also include side visits to stay in touch with the creek as we walk it's length. This is mostly bush trails, but initially some (short) urban walking. Wear: Trail runners, hiking shoes as this can be muddy/slippery, even if rain was several days ago. Bring: 2-3 liters of water - stay hydrated Public transport options: Note: The metro may be out again. Train from Central to Pennant Hills Station 7:03am Platform 18 to Pennant Hills at 7:45am is best. 626 Bus from Stand A 8:05am (Pennant Hills Road side of Station) to Victoria Rd before Cardinal Ave stop We finish at Asquith station, so you can get public transport back to Pennant Hills - or wherever you need to get to. Starting point is [here](https://what3words.com/jets.below.plays) If getting the bus from Pennant Hills Station to the start meeting point is [here](https://what3words.com/fonts.tribal.chins), next to the Pennant Hills Pub and and you want 626 Bus. Pete will be there. I (Chris) will be at the start

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4 attendees
Great North Walk Thornleigh to Chatswood 18km medium

Great North Walk Thornleigh to Chatswood 18km medium

Sat, Aug 1, 11:45 PM
From Aussie Explorers
4.8

Fabulous walk along the Great North Walk trail from Thornleigh Station to Chatswood Sation about 18km and a few small ups/downs but lovely bush trails ## Lane Cove National Park & The Great North Walk Sydney is incredibly fortunate to harbor a significant number of national parks right within its metropolitan boundaries. Among the most central is **Lane Cove National Park**, which begins less than 10 kilometers from the CBD as the crow flies. While surrounding suburban development has introduced some weed encroachment along the creeklines, the park beautifully preserves a wealth of original, pristine bushland across its ridges and valleys. For walkers looking to explore this pocket of wilderness, a prime section of the iconic **Great North Walk**—the massive track linking Sydney to Newcastle—cuts directly through the heart of the valley. This specific route follows the peaceful, non-tidal waters of the Lane Cove River, tracing the valley from the weir at Fullers Bridge all the way up to the northern watershed near Thornleigh. For transport info please visit [http://www.transportnsw.info/](http://www.transportnsw.info/) Around 16km medium grade a couple of ascents and descents but and track is rough in places. Should be into Chatswood station about 3:30-4:00pm ish, time for a cold beer across the road from the station! $10 fee applies to this event which can be paid in cash on the day or PayID is 0402 251036 David Matthews Make sure you have plenty of snacks think carbs/sugar as protein takes too long to process. Do not skip salt... Your body requires energy to complete longer walks... Bring a jacket in case of a change of weather and 2l of water, sturdy walking shoes/boots, hat suncream, snacks and lunch! Nowhere to top up along the way either water or food! SAFETY WARNING: Please stay away from cliff edges and be very careful when walking on wet and slippery rocks and surfaces. Please stay within sight of the group at all times and do not walk in front of the leader. If you get lost you are on your own and must find your own way out. DISCLAIMER: Your health and safety is our priority and 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 RSVPing 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](https://www.meetup.com/Aussie-Explorers)]([https://www.meetup.com/Aussie-Explorers](https://www.meetup.com/Aussie-Explorers))

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25 attendees
"SPIT to MANLY" to BEACHFRONT MUDGEE WINE FESTIVAL HIKE!!!

"SPIT to MANLY" to BEACHFRONT MUDGEE WINE FESTIVAL HIKE!!!

Sat, Aug 22, 11:30 PM
From WE HIKE. WE WALK... to the BAR. Social Sessions in Sydney
4.9

The “**Manly Beach to Spit Bridge Hike**” is… ***So. Damn. Beautiful.*** It's widely considered the prettiest of the Sydney Harbour hikes. And? We’re adding **Chinaman’s Beach** \- one of the sleeper Sydney beaches\, and perhaps it’s the best\. Let’s do it all\, and finish at stunning **Balmoral Beach**. And guess what's on just next to the beautiful beach? **[The Mudgee Wine & Food Festival!!](https://mudgeewine.com.au/mudgee-wine-food-festival-balmoral/) 12kms total hiking!** **THE HIKE.** There's so much to write - but I won't. You have to see it with your own eyes. **Manly Wharf to Spit Bridge.** **East Manly Cove Beach.** **West Manly Cove Beach, Manly Pavilion, Forty Baskets Beach, Reef Beach** which spills into a diverse bush walk in **Sydney Harbour** **National Park**. Harbour views. Secluded Beaches. Wildlife. Mansions on the water to **Clontarf and Spit Bridge**. Crossing Spit Bridge we’ll enjoy a solid rest at **Chinaman’s Beach** – you’re in for a real treat. After Chinaman’s, we’ll neighbourhood / bush walk down to **Balmoral Beach** – another delightful Sydney spot. **[If you join, please come back here and jump into our whatsapp group by clicking on this link. It's a must to come to our events. Thanks!](https://chat.whatsapp.com/KNM1VuJllX0JwAWpiCpADd)** **THE WINE FESTIVAL & BEYOND.** a) Let's have a quick perve at **Mudgee Wine Fest** \- 20 wineries and 15 food vendors \(feel free to buy tickets and stay long\)\.\.\. then take a 7min bus up to: b) **The Buena** is one of the nicest pubs in the lower north shore, and the rooftop section is really cool. I'll also say this - it's not on any 'Best Sunday Roasts" list, but it's absolutely delicious and it should be. **THE TRANSPORT.** a) **Manly ferries leave Circular Quay to Manly every 10-15minutes.** Please check your tavel apps - we’ll head off from **Felon's Seafood (not Felon's the bar) at 930am**. It's just next to Hugo's Manly. Arrive early! **Manly Corso is** lovely to check out early. b) From **Balmoral Beach** there are buses o'plenty up to The Buena on Military Road then into the city. See you for a beautiful hike, beers, and laughs. MJ **THE OTHER STUFF** a) **Be on time.** If you’re late? Catch up. Please don't call, message. Just catch up. b) Gratuity for this hike is **$10** Cash or PayID. c) **Fitness matters here.** Sure, the pubs sound great, but we are hiking in National Park. Be prepared. d) **Honour your RSVP.** No shows get banned from the group. **I put my credit card down for a reservation – your reservation.** e) Bring mates, dates, etc... f) **Go back. Read the event. And join the whatsapp group!** ***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? Awesome! Send me a note first please - let's chat about your hiking experience and fitness.

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40 attendees
🌸CQ🌸MARITIME MUSEUM🌸SYDNEY FISH MARKETS🌸IRON COVE🌸BALMAIN🌸🌸

🌸CQ🌸MARITIME MUSEUM🌸SYDNEY FISH MARKETS🌸IRON COVE🌸BALMAIN🌸🌸

Thu, Aug 13, 12:15 AM
From Aussie Explorers
4.8

MEETING: Circular Quay Wharf No2 🌸✈️🌸 TIME: 10:15am 🌸⏰🌸 DETAILS: We walk from CQ via Dawes Point, Barangaroo, Cockle Bay to The National Maritime Museum to spend 30 minutes perusing the FREE exhibitions…. There are several, then Pyrmont to the newly opened Fish Markets, via Glebe through Lilyfield to Callan Park, then along the Iron Cove River to Rozelle and finally Balmain East for the ferry ride back to the city 🌸⛱🌸 LUNCH: Sydney Fish Markets. If you wish to byo there are many places to sit and take in the view. 🌸🍽🌸 COST:💲5️⃣ cash gratuity or (donation)for this walk.💵 🌸💲🌸 DISTANCE: 1️⃣4️⃣kms 🌸🦋🌸 THIS WALK IS GRADED AS: Deliciously easy, with a few stairs thrown in. 🌸☀️🌸 GET OUT POINTS: the entire way 🌸🚦🌸 TRANSPORT: Return ferry from Balmain East 🌸✈️🌸 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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15 attendees
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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.