Ride9
City Ride 9 - Waterloo to Wilson St
Modern Zetland to Bustling Newtown
If you look at a map of Sydney’s cycling network, there’s a distinct personality split. On one side, you have the shiny, master-planned boulevards of Green Square and Waterloo. On the other, the organic, gritty, heritage-lined arteries of Newtown and Erskineville.
Ride 9 is about bridging that gap and demonstrating some of the paths developed by the City Of Sydney.
This isn’t a simple A-to-B cruise on a single separated path. This route is a mix of brand-new infrastructure, quiet backstreet connections, and a few “missing links” that require a bit of local knowledge. It’s the essential connector for anyone trying to get from Zetland into the heart of the Inner West without battling the traffic on streets like McEvoy Street. Then the ride demonstrates two north south paths at each end. It is highly unlikely you will use all the path in one go, just bits and pieces of it to get around.
Let’s ride.
The Launch: Gadigal Avenue
We start in the “New World” of Zetland. Rolling down Crystal Street and Gadigal Avenue, you feel the scale of the urban renewal here. It’s wide, modern, and feels almost European in its layout. This is the easy part—the separated cycleways here are generous and clearly marked. But enjoy it while it lasts, because the real navigation test is coming up.
The Green Square Shuffle
This is the section we discussed—the “Choice A” tricky bit. The transition from Green Square (the wonderful library) over to Alexandria isn’t fully intuitive yet.
Navigating from Gadigal onto Bowden Street feels like finding a secret passage. You have to thread the needle through the Geddes Avenue intersection and make the jump across to Harley St and Ashmore st . This “missing link” in the network has recently had a few upgrades. It’s not perfect yet, but once you know the line, it unlocks the entire route. It turns a frustrating barrier that is the busy intersection of Botany St and o’Riordan St into a manageable crossing.
The Alexandria Transition
Once you clear Bowden and hit Harley and Ashmore Street, the vibe shifts immediately. You’ve left the high-rises behind and are back in the land of terraces and single storey warehouses. This section through Alexandria is all about flow. It’s quieter, lower stakes, and leads you toward the rail line.
The Erskineville Area
Ashmore Street ends at the railway line at Bridge Street, where you pick up a short separated cyclepath running alongside the tracks heading North. But keep your wits about you for the next move.
You’ll need to cross the railway and then prepare to turn into Burren Street. This turn has to be made from the centre of the road, and it can be a little tricky with traffic. Don’t rush it—take your time, signal early, and wait for a clear gap before committing to the turn.
The Arrival: Wilson Street
The payoff for navigating those gaps is arriving at Wilson Street from the east. We’ve talked about Wilson Street before, but hitting it from this direction feels like a victory lap. You have arrived near the Carriageworks vibe, onto the separated cycleway, and suddenly you are plugged right into the main artery of the Inner West. You can head to Sydney Uni or ride through Newtown to Petersham on Ride 7.
Check out Ride 9 here in
RideWithGPS City Ride Collection (ride 9) On CycleSydney Map
These photos are shown in location in the video that follows
And here is a highlights video of the ride from Waterloo to Newtown (Wilson St)
In our first month or so, this newsletter has now grown to 100 readers. Thanks for being pioneers and I hope there is safe, interesting riding for you in 2026. Garry from CycleSydney