The Serpentine (Upwey)

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The Serpentine
Distance: 700 m
Average Gradient: 13%
Elevation gain: 91 meters
Traffic: Light traffic
Surface: Sealed
Category: 4

Here is a link to the Strava segment here:

The switchback design of this road was the only way to reduce the hills naturally steep gradient.  This road was appropriately named “the Serpentine”.  This came about due to the fact that the road looks like a coiled snake on the map.  This is a must do climb which you have to try at least once.  You’ll feel the sharp sting as you each switchback is incredibly challenging and brutal.  And whilst only short in distance, your heart rate will be going through the roof.   Virtually every rider who attempts this climb is forced to rest at the top.  Dry reaching and gasping for breath.   Its an iconic climb which was made popular by being featured in several editions of the Dirty Dozen series.

The Serpentine


The Serpentine climb

The climb begins at the corner of Sandells Road & the Serpentine.


The Serpentine is a tough climb as the surface can be rough.  And the road is just over a car length wide & it is a two way street so keep an eye out for traffic.  There aren’t that many houses on this road.  Thankfully you will most likely encounter local traffic only and rarely will see a car on this climb.  The gradient does not drop under 10% and is steep throughout. The climb consists of 5 switchbacks.  The hardest parts are the corners where the gradient ramps up well in excess of 20% each corner.  Each corner wearing away more and more at your legs.


The climb finishes when you reach the intersection at Terry’s Avenue .  This is considered one of the Dandenong’s toughest climb.  If you have anything left in the legs after climbing the Serpentine its well worth hitting Terry’s as well.

What to expect

  • Very narrow street (two way traffic)
  • Incredibly steep and brutal climb
  • Local traffic only
  • The steepest part of the climb are in the corners which peak at around 20%
  • Well shaded climb

Plan your ride

Upwey is located approximately 40 km east of Melbourne.  If you’re taking public transport.  Train services are available to “Upwey” train station.  Click here for Public Transport Victoria for train timetable.

During fire season

The Dandenong Ranges are in a fire district. Anyone entering parks and forests during the bushfire season needs to stay aware of forecast weather conditions. Check the Fire Danger Rating and for days of Total Fire Ban at or call the VicEmergency Hotline on 1800 226 226.

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One thought on “The Serpentine (Upwey)

    Radio Snivins said:
    January 7, 2018 at 2:39 am

    I”m still trying to conquer Terry’s Ave to get to The Serpentine.

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