Lower North Shore to Eastern Suburbs

Wollstonecraft to Watson’s Bay. The best ride!

Lachlan Soper Lns Eastern Suburbs Map

Score: 9.5/10.

Gee what would make it 10/10? It’s only small stuff… perhaps:

  • Children being allowed to slowly ride their bikes through the Botanical Gardens footpath, which is currently not permitted. 
  • Flattening “Heartbreak Hill” and the hill in Darling Point 😉. Seriously, I need to check out next time whether the kids can ride along Tivoli Ave and the Hermitage Foreshore Walk, rather than up Heartbreak hill and down Vaucluse Rd. 
  • But, I can’t say this often enough, this is a world class day out for a family that loves exercise and, views and the outdoors.

Star Rating For Difficulty (out of 5): Star IconStar IconStar Icon

3 star because there’s a bit of elevation. The hills are around: Wollstonecraft to Waverton, HMAS Kuttabul Potts Point, Darling Point, and Heartbreak Hill Rose Bay. But none of them are super steep or substantially long, compared with some of the others encountered on the Lower North Shore rides.

Notable Sites, Cafés, and Playgrounds Along the Way:


This is not just a ride to go on with your kids, this is one to do as a cruisy ride with your cycling mates (if you’re a cyclist) or to take your out-of-town guests along. It’s a brilliant way to see one of the most iconic harbours in the world, with its Bridge, Opera House and everything else!

There are so many good places to eat, playgrounds, picnic spots, and amazing sights to see on this ride. Get up early and allow all day to take it at as slow a pace as everyone wants!

We start this ride with a short loop around Wollstonecraft, if you want to eliminate the short and sharp hill up Shirley Rd, then skip this part, but it’s a great view of the harbour. We then meander through some relatively quiet streets in Wollstonecraft and Waverton to The Coal Loader. This is actually much better than you’ll expect, kids like weaving around there on their bikes, then looking at the old ships and the nearly fallen down wharf. Take the elevator down to see the chickens of various colours and then another level down to ride under and through the coal loader and then back the other direction to see the naval ships at HMAS Waverton. You’ll be surprised how much time kids will happily spend here. 

From there we take some back streets through North Sydney and take the zig-zag path from the end of Munro St to Sawmillers Reserve. Regardless of how competent your children are at bike handling, we’ve decided that it’s best to walk down this zig-zag path, it’s steep with tight corners for little people to negotiate. It’s not a long walk. 

When we get to Blues Point Road we walk our bikes up the short and very quiet Parker St (noting we are walking against the one-way traffic direction). Then it’s some quiet back streets, a short section of footpath riding on Lavender St and then down to Watt Park where we usually stop for our first playground and drink. Parents, take your time to enjoy the world-class view from Lavender Bay boat ramp past Luna Park to the Harbour Bridge and the Opera House. 

We then slowly ride towards and past Luna Park, being careful of pedestrians and also soaking in those amazing views. From North Sydney Pool it’s a sharp little pinch up to the Harbour Bridge Cycleway stairs, where parents may need to do a few laps up and down to help get the bikes up. The ride across the Harbour Bridge is always an amazing blessing with views Westward to Luna Park, Parramatta River, the Blue Mountains (on a good day), and Barangaroo. 

When we get off the Harbour Bridge we like to wiggle around Barangaroo, which again has another great aspect through the Harbour Bridge (particularly as you descend from the top of Barangaroo), and then slowly around the piers in Walsh Bay. Keep an eye out (it’s hard to miss) for “Still Life With Stone and Car” on the roundabout on Hickson Rd. The kids love going onto that roundabout and checking it out up close.

After Walsh Bay we ride slowly on the footpath on the Harbour side of Sydney Overseas Passenger Terminal (watch out for the rail tracks), which has a stunning up-close view of the Sydney Opera House, then even slower around Circular Quay and stop to suck in all the sights of Sydney Harbour from the Northern aspect of the Sydney Opera House. After pausing here, we make our way through the foreshore of the Royal Botanic Gardens to Busby’s Bar for a bite to eat. The food is nice, you can relax on the grass of the Botanical Gardens or sit at a table, and in a peaceful manner enjoy views to die for. Beware – neither you nor your kids can ride (or even sit on the bikes without pedalling) through the short section of the Botanical Gardens, it is strictly patrolled.

Upon resuming riding, it’s up and around Mrs. Macquarie’s Chair, with views towards the Harbour Bridge, Admiralty House, and Fort Dennison as you ride Northward, and then towards the naval ships at HMAS Kuttabul when riding southwards. In Woolloomooloo there are usually some cool sculptures along the boardwalk on the Western side of the waterway, our favourite is the dragon (which may or may not still be there).  There is a steep and short little hill coming out of HMAS Kuttabul into Potts Point. The footpath is narrow, but my preference is for my kids to ride up this footpath, rather than the road without a bike lane. The children find the change in architecture in Potts Point interesting and it’s a good conversation to engage in. We continue along the footpath until dropping into Rushcutter’s Bay Park and then have a coffee / brownie / croissant at Flybridge café in d’Albora Marinas. 

Continuing along to the end of Yaranabbe Park gives the kids a chance to see some people fishing and check out the catches of the day. There is then a short, but tough climb into Darling Point. If your kids cannot ride it, it’s not a long walk before the left-hand turn. We ride on the footpath along Darling Point Road and the kids love looking at the “mansions”. We drop down the hill from St Mark’s Anglican church to Steyne Park, next to Double Bay Beach, which has a nice playground which is well shaded and is another great opportunity to have a drink and a snack and a play. 

From here, with kids, it’s footpath riding along New South Head Rd to Vaucluse Rd (partway up Heartbreak Hill). That being said, the path along Rose Bay is wide and the views are great. At Rose Bay the kids often like to stop, rest and play at Lyne Park Playground, which is well shaded, has a nice flying fox and you can see (and hear) the sea planes taking off (which is always exciting for the kids). They also find the (not infrequent) sightings of Aston Martins, Ferraris, Lamborghinis, and other rare and expensive cars in the carpark near Catalina restaurant an unusual treat.

Rose Bay has some good shops for food, including chicken shops and a bakery. If you can put whatever food or drink you may choose to purchase into your backpack for the 2.5km to Strickland House, you are unlikely to regret it (more to follow). 

Heartbreak Hill (New South Head Road), albeit long-ish, isn’t super steep, so if your kids have gears, tapping it out in the lowest gear is possible. Just be careful of the two road crossings. It’s then downhill to Strickland House Estate. This is worth planning a long stop at. The house is lovely, but the views (and these are the last direct views towards Sydney Opera House and The Harbour Bridge on this ride) are to die for. Lie down on the luscious grass, find a shady spot in Summer or a sunny spot in Winter, pull out your fruit drinks and your food, and have some slow time in the gardens. My kids love to play “Hide ‘n seek tip”, just remember the grounds of the two heritage houses on this estate are very large, so it may be safest to take a “peek” in the direction the kids are going 😉

We then venture around to Greycliffe House, which is perhaps more beautiful than Strickland House, and then down to Vaucluse Bay. It’s then some slow riding along Coolong Rd and Wentworth Rd / Fitzwilliam Rd Vaucluse. The kids enjoy more “mansion” spotting, and by now their future dream house has got to 3 stories with a fireman pole, ballroom, games room, indoor pool, and a zip line just for starters! The conversations and tangents that occur with children on these rides are priceless, conversations that would never happen in the busyness of home and normal extra-curricular life. 

Keep an eye out not to miss the turn off to Parsley Bay Suspension Bridge and take time to stop along it and suck in the view of the bay, beach, and harbour. We have usually got here towards the end of the day, but Parsley Bay Reserve, Beach and Playground look spectacular, and it may be worth taking swimmers in the backpack for a well-deserved swim here prior to ending up in Watson’s Bay. 

The ride makes its way to Watson’s Bay from Parsley Bay, another beautiful part of Sydney which deserves plenty of slow time too. If possible, start the ride early (like 7 or 8am) and plan to have takeaway Fish and Chips at Doyle’s on the Wharf Watson’s Bay.

If you can time your ferry ride back to Circular Quay a little before sunset, you will get some of the most amazing deep orange and red sunsets through and under the Harbour Bridge. It’s then another ferry to Luna Park, up to Milson’s Point Station, and a train back to the car at Wollstonecraft. 

From here, with kids, it’s footpath riding along New South Head Rd to Vaucluse Rd (partway up Heartbreak Hill). That being said, the path along Rose Bay is wide and the views are great. At Rose Bay the kids often like to stop, rest and play at Lyne Park Playground, which is well shaded, has a nice flying fox and you can see (and hear) the sea planes taking off (which is always exciting for the kids). They also find the (not infrequent) sightings of Aston Martins, Ferraris, Lamborghinis and other rare and expensive cars in the carpark near Catalina restaurant an unusual treat.

Parking & Toilets


We usually park in Russell St Wollstonecraft, where you can usually find a park and ride through the bike / walking path towards Wollstonecraft station. Note, there are parking limits. It may be best to find a street with all day parking for the day you are riding.


The Coal Loader

Near Lavender Bay jetty (between Watt Park and Peter Kensington Walkway towards Luna Park).

Just above Busby’s Bar on the Eastern side of the Royal Botanic Gardens. 

Strickland House (port-a-loos, but usually quite clean).

Robertson Park, Watson’s Bay

As well as at many of the eatery options along the way.

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The information provided on this website is for information purposes only and it may not be complete. No responsibility is accepted for any liability, loss or risk which is incurred as a consequence of the use of any of the material or links on this website. We are not responsible for any road / path blockages or changes. It is the parent’s responsibility to ensure their bikes are in good working condition and to assess their child/children’s abilities according to their age, strength and fitness and to select a route that is at their level and where they can be safely supervised. It is wise for parents to start off with shorter, easier rides and check in regularly with the child/children for safety and be alert for any signs of dehydration, sunburn, fatigue or weather impacts. Links to external websites do not constitute endorsement, sponsorship or recommendation. Nothing on this website is commercialised or paid advertising. Opinions are entirely my own.

-Lachlan Soper