This is a well developed trail with detailed history boards, which winds through a variety of suburbs and urban parkland. From Fairfield to East Malvern it is known as the Anniversary Trail. Between East Camberwell and Alamein it runs beside the Alamein railway line. There are many busy road crossings, but most have lights.

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You can cycle from Kew to Elsternwick by combining the Outer Circle and Rosstown rail trails. Total distance: 25k

This description describes the trail heading south to north.

From East Malvern to Kew it is also known as the Anniversary Trail.

Hughesdale to East Malvern (2km)

The trail begins at the impressive Hughesdale Station on the Dandenong railway line and the Djerring Track beneath the “Sky Rail”. You can also join in nearby Boyd Park, very popular.

At six-lane Dandenong Road, it is safest to follow the service lane to the west for 200m to cross at the lights. Then turn north again, and enter the Urban Forest, once the site of the Waverley Road Station. This is a beautiful native bushland park with several trails running in parallel. Follow any of these to arrive at Waverley Road. This is the only unsealed section of the trail. Cross the road, and pass through East Malvern Station carpark. The trail meets the Scotchman’s Creek Trail here, which you could follow to your right all the way to Jells Park.

East Malvern to East Camberwell / Canterbury (7km)

Use the pedestrian and cyclist overpass bridge to cross the Glen Waverly Railway line and the Monash freeway. The trail runs through Malvern Valley Public Golf Course.

Stick carefully to the trail and at the golfing tee-offs, head north to cross Gardiners Creek and get back on the original alignment (the Gardiners Creek Trail keeps heading west). Once a long timber rail bridge crossed Gardiners Creek at this point.

The trail is now known as the Anniversary Trail and very picturesque until Alamein railway station. There are the old railway catenary poles still carrying electrical wires overhead although there were never any electric trains in this section!

From Alamein station the trail is beside the Alamein railway line. At several intersections, cars must give way to pedestrians and cyclists – but keep a look out anyway.

The shops at High Street are a good place to stop for a coffee. Soon after is a steady climb, with the trail running up the side of the train line’s cutting. The next crossing, Toorak Road, can be very busy, and has an extremely steep (but fortunately short) hill on the far side. Things then get easier as the trail winds its way past the Hartwell, Willison and Riversdale stations. After Hartwell station the trail moves off the rail alignment and at Prospect Hill Road it winds around a hockey club, before passing under the Belgrave/Lilydale Line at East Camberwell station and turning northwest into Boorondara Park.

Canterbury to Kew (8km)

The trail is now a “proper” rail trail again, on the formation of the former railway. Shortly after passing under Canterbury Rd the trail is in a deep cutting for several kilometres – a somewhat hidden gem of tranquility buried in the eastern suburbs. This section is particularly busy before and after school so don’t expect tranquility at these times.

At High St. Kew, cross at the lights to your right, to get through busy Harp Village junction. From here, it’s a long descent down to Chandler Highway with the former formation to the left.

The formation and Anniversary Trail ends at the Eastern Freeway but there is a bike path to continue over the freeway on to the Yarra River, albeit narrow and noisy.

It is worth it though as this is the connection with the Main Yarra Trail and the Yarra River bridge which is a real feature. The railway bridge was converted to a two land road bridge when the railway closed and was one of Melbourne’s most congested roads until 2020 when a new six lane road bridge opened to the south and the former railway bridge became the rail trail bridge with many interesting features including portholes to the river below.

Between the Yarra River and Heidleberg Road is the former Australian Paper Mills site where a lot of urban renewal development is underway so the view here will change regularly.

North of Heidelberg Road, the rail corridor curve to the west. It has not been developed, and remains as vacant land. There is a short section of path to Fairfield Station on the Hurstbridge Line.