Double Bay to Waverley: The Eastern Suburbs Harbour & Hills Trail
Ride 19 - Rose Bay to Waverley Park
Today, we're heading out on a scenic ride starting at the Double Bay Wharf and traveling all the way up into Bronte. We're going to stick to the available shared paths as much as possible, tracing a really nice section along the water at Rose Bay before making our way up towards Bondi Junction. From there, we’ll take a turn to cruise through Waverley Park before finally rolling down to Bronte Heights for the finish
Map link >> RideWithGPS Link Full Ride Video on YouTube
Double Bay to Rose Bay
We kick this ride off at the Double Bay Wharf ⛴️, cruising along the tiny beach before heading over to William Street. While we start on the road, it’s not long before we hit New South Head Road and jump straight onto the shared path near the Red Leaf Pool. Be prepared to share this stretch with a lot of walkers and runners who are also out enjoying the scenery.
Make sure to keep an eye out for Red Leaf Beach. It’s a council area with a fantastic, shark-netted beach and a terrific little cafe hidden right under the cliffs—the perfect spot to snap some photos of Double Bay out towards Clark Island 📸. After popping back onto the slightly bumpy New South Head Road shared path, you have the option to take a on-road detour around Point Piper via Wolseley Road. It’s usually a quiet stretch where you can catch glimpses of the water, the Harbour Bridge, and what the really rich and famous like to call home.
Heading back to the main route, we hit the Rose Bay area. The path along Rose Bay is good but busy with walkers for good reason. The boat scenery is magnificent. This terrific cycleway shared path starts at the police station and goes down to the Rose Bay Wharf, which is a great destination if you want to jump on a ferry with your bike or end your lime bike journey.
We cross New South Head road at Kent Road near the massive Royal Sydney Golf club house, and a bouncy track follows New South Head road for a bit. Check the photos
The Rose Bay cycleway was a contender in 2022 for the Sydney Infrastructure Awards. That was a great year for the Eastern Suburbs with the Bondi Cycleway and Queens Park in the top 3 that year.
Rose Bay to Bondi Junction
We tackle the shared path on the south side, ducking through the apartment blocks on Norwich Road and Lane to find the shared path that wraps around the eastern side of the golf course. It’s a nice stretch offering glimpses of the famous greens ⛳.
When you pop out at O’Sullivan Road, you’ll need to head up the road for just a bit to find a safer crossing. Now, brace yourself for Birriga Road. If you’re heading up, you’re going to hate me because it’s a steep, on-road climb all the way. There is a cycling section that is ok. Take note of an unusual little off road notch on a tight corner where you can hop onto a small path to catch your breath. If you’re heading down Birriga, you will be tempted to go really fast going down it. Be less tempted.
At the very top, you’ll find Bellevue Park (a small detour) which offers some fantastic, long-distance views to the east and north towards the harbor. From here, we join the Old South Head Road shared path, which is a bit bumpy and heavily populated with walkers heading toward Bondi Junction.
Bondi Junction to Waverley Park
Instead of fighting the foot traffic and the bumpy shared path all the way up to the Bondi Junction cycleway, we take a turn down Paul Street and head towards the Waverley Council building. Traffic really thins out here as we roll into Waverley Park. The shared paths through Waverley Park do the trick.
Exiting the park drops us onto Henrietta Street, which features one of the more unique cycleways in Sydney. It’s an unusual two-way bicycle and one-way car street, boasting a green contra-flow path that lets riders go directly against the traffic. Keep your wits about you at Victoria Street, where there is a little crossing and the road magically changes direction for the cars in the middle.
The dedicated path stops at the end of Henrietta Street, as it is all on-road from then on. You’ll end up on Bronte Road, and if you want to cap off the ride with a swim, simply turn off at Gibb Street and cruise straight down to Bronte Beach 🌊.
For our paying subscribers, here are a few extra local tricks and alternative routes to conquer those Eastern Suburbs hills!
