The trail can be enjoyed in various bite-sized pieces. Car parking can be limited and generally requires using side streets or railway stations. There are water fountains, toilets and bike repair stations at regular intervals.

This description covers the trail travelling southwards, away from Melbourne.

Fairfield to East Camberwell (8km)

• The corridor starts east of Fairfield Railway Station, which is on the Hurstbridge line. There is a short section of concrete path along Railway Place, but that soon peters out as this section is yet to be re-developed as part of the trail. From Heidelberg Rd the rail trail proper starts beside the Chandler Hwy. Between here and the Yarra River is the former Australian Paper Mills site, which used a section of the Outer Circle track as a siding. Here a lot of urban renewal is underway, so the view will change regularly.
• The Yarra River Railway Bridge is a real feature. Built by Sir John Monash as a young engineer, it was converted into a two-lane road bridge after the railway closed and went on to become one of Melbourne’s most congested arterials. A six-lane road bridge opened to the south of it in 2020 and the former railway bridge finally became the rail trail bridge. It has many interesting architectural features, including portholes to the river below. On the south side of this bridge are connections with the Main Yarra Trail heading east and west.
• There follows a narrow and noisy shared path over the Eastern Fwy and the start of the “Anniversary Trail” section. It’s a long ascent next to the former formation (minus trestle bridge) up to High St, Kew East. Cross at the lights to get through busy Harp Junction, where the train underpass has been filled in. The trail is now a “proper” rail trail again, on the alignment of the railway. Until it passes under Canterbury Rd, the trail is in a deep cutting for 1km – a somewhat hidden zone of tranquillity in the eastern suburbs. This section is particularly busy before and after school, so don’t expect tranquillity at those times.

East Camberwell to East Malvern (7km)

• The trail passes through a substandard section in Boorondara Park and then goes under the Belgrave/Lilydale Line near East Camberwell Station. From here the trail is well away from the rail alignment for a while and, at Prospect Hill Rd, it even winds around a hockey venue. It then heads past the working Riversdale, Willison and Hartwell stations. It runs beside the Alamein line but undulates. The next crossing, at Toorak Rd, can be very busy, and has an extremely steep (but fortunately short) descent. Cafes here, or at High St, are a good place to stop for refreshment.
• The end of the working line is reached at Alamein Station and a very picturesque stretch starts with old railway catenary poles carrying high-voltage wires overhead for the suburban network, although there were never electric trains running on this section! The Anniversary Trail section ends at the Gardiners Creek Trail intersection. Once a long timber trestle bridge crossed the creek’s floodplain at this point. After crossing Gardiners Creek, the trail runs through Malvern Valley Public Golf Course.
• Stick carefully to the trail and, at the golf tees, head south to get back on the original alignment (the Gardiners Creek Trail keeps heading towards the CBD). Use the shared-use bridge to cross the Monash Fwy and Glen Waverley line. The Outer Circle meets the Scotchmans Creek Trail here, which you could follow east all the way to Jells Park.

East Malvern to Hughesdale (2km)

• Make your way carefully through the East Malvern station carpark and cross Waverley Rd. After Waverley Rd the trail passes through the Urban Forest (enter from the carpark on the left or stay on the bitumen trail to the right), once the site of Waverley Rd Station. This is a beautiful, native-bush park with several paths  running in parallel and features the only unsealed section of the Outer Circle. Keep an eye out for Pobblebonk frogs.
• Head south to busy Dandenong Rd/Princes Hwy. Head west 200m to cross at pedestrian lights then follow the service lane to the east for 200m to rejoin the rail trail. Wonder why the pedestrian crossing is so far away. The trail passes through Boyd Park before ending at impressive Hughesdale Station, on the Dandenong line’s Sky Rail section with Djerring Trail underneath. You can start from this end of the Outer Circle (look for the Boyd Park sign) and head towards town, a very popular option.

Bonus track

You can cycle all the way from Kew to Elsternwick by combining the Outer Circle and Rosstown rail trails for a total distance of 25km.