The Course

Highland Fling

The 2016 Highland Fling will once again offer riders four race distances:

  • Full Fling – Approximately 110km
  • Half Fling – Approximately 60km
  • Some Fling – Approximately 23km
  • 100Mile Fling – Approximately 160km
Ride through lush farmlands
Ride through lush farmlands

The Highland Fling follows a unique route that takes riders on a journey from the event centre down country lanes and onto farmland tracks, before directing them back into forests, including Penrose and Wingello State Forests. The course also gives riders access to some of the beautiful private properties surrounding the town, and the not otherwise accessible singletracks they feature, and challenges legs and lungs with some 2300 metres of climbing (Full Fling) – which of course means 2300 metres of descent as a reward!

Discover private trails

The Half Fling and Some Fling enjoy shorter versions of the Full Fling course, including the Jumping Rock private property section of singletrack (available to ride only during the Highland Fling), while the 100Mile course lets riders enjoy the Wingello Forest for a second time.

All distances see riders return to where they started, riding through the finishing arch to the cheers of spectators on the sideline, and a well earned 4 Pines Beer as a reward.

Routes and Maps

Event Centre Map

Event Map_HF logo

MTB Trails of The Southern Highlands Map


The NEW 5th Edition of our MTB Trails of The Southern Highlands Map is now out and can be purchased for $19. This map includes the route of the Highland Fling.

The Southern Highlands of NSW offers a wealth of riding opportunities for road and mountain bikers alike all within 2 hours of Sydney, 1.5 hours from Canberra and 1.5 hours from Wollongong. Quiet country roads, expansive State Forests and National Parks all make for a cycling paradise. This double sided map and guide suggests some of the rides available to mountain bikers as well as covering a large area allowing you to plan your own rides. The 5thEdition of this 1:25000 scale map includes the route of The Highland Fling, the Wingello State Forest MTB Trails, the classic tour from the Highlands to Kangaroo Valley and much more. Price: $19 per copy (includes mailing).

Outline Route Map – Full Fling

Click on the above image to use our interactive course map. Please note this route is not final, we are still finalising some fun new inclusions and tweaks to the 2016 Highland Fling.

Outline Route Map – Half Fling

Click on the above image to use our interactive course map. Please note this route is not final, we are still finalising some fun new inclusions and tweaks to the 2016 Highland Fling.

Outline Route Map – Some Fling

Click on the above image to use our interactive course map.

Route Description

The Full Fling follows a unique course taking riders out from Bundanoon along undulating farm tracks into Penrose State Forest through the famed Early Bike Wash. After winding through the pines of Penrose, you’ll descend to cross Paddy’s River and follow a mix of farm tracks and trails to Wingello to complete the Ground Effect Stage 1. From here, you head out on a loop through the beautiful forest and gully country of Wingello State Forest including the much loved Wingello singletrack. Returning to Wingello village, you’ll have completed the Shimano Stage 2. Leaving Wingello on a different route back into Penrose State Forest before tackling the loop of singletrack on Jumping Rock on your way back to Bundanoon to complete the GU Stage 3. All but 2km of the route is on dirt – singletrack, open paddock, rough tracks or dirt roads. The profile includes a total of some 2350m of enjoyable climbing … and given you finish back where you started, that means 2350m of sweet downhill! The Full Fling has a test for you all!

If you choose to ride the Half Fling, you’ll complete the Ground Effect and GU stages. Or if the Some Fling is your choice, you’ll enjoy the first section of the Ground Effect stage and the last half of the GU stage. And if you’re up for the 100Mile Fling, you get to complete all three stages, including the Shimano Stage through Wingello Forest twice!

Track Breakdown

One rider’s (or event organiser’s!) singletrack is another rider’s (or event organiser’s) 4WD track. There is no Australian Standard! The breakdown of the 2016 Highland Fling is something like:

  • Full Fling – 30% Singletrack, 54% Rough/4WD track, 14% Dirt Road, 2% Sealed Road
  • Half Fling – 20% Singletrack, 62% Rough/4WD track, 15% Dirt Road, 3% Sealed Road
  • Some Fling – 37% Singletrack, 32% Rough/4WD track, 18% Dirt Road, 13% Sealed Road

Please do not attempt to ride the private property sections of the course at any time, as to do so will jeopardize the event.

groundeffect Ground Effect Stage (24km): Full Flingers, Flinging Threesomes, Half a Fling, Some Flingers (part), 100mile Flingers


We’re still finalising the course of the Ground Effect Stage for 2016, but it will be similar to previous years.

On leaving Ferndale Oval you will charge down a brief section of blacktop before hitting the dirt.  After 2km or so you’ll enter private property and follow an undulating farm track out into Penrose SF, and your first opportunity to clean your bike (!) at the Free Bike Wash. Some Flingers will miss out on this opportunity, turning left and heading straight for the singletrack section of the GU stage (see below).  The rest of the field ride along forest tracks through the pines of Penrose before descending into more private property to cross Paddy’s River. A great section through farm paddocks and private forest follows before you pop out into the Transition Zone at Bill O’Reilly Oval in Wingello village.

Wingello Oval Transition Area: Full Flingers, Flinging Threesomes, Half a Fling, 100mile Flingers [Transition Area Map]

After passing through the timing station, Half Fling riders will proceed directly to the GU Stage (see below). They can choose to stop here but their time will continue throughout the transition stop.

The race times of Full Flingers, Flinging Threesomes and 100mile Flingers will be paused for a period of up to 5 minutes. The reason for this is the level crossing in Wingello. In order for riders to get to the start of the Shimano Stage safely and without being disadvantaged by having to wait at the level crossing in the unlikelihood of a train passing, we will allow a maximum of 5 minutes before your time automatically begins again. If you choose to proceed through the next timing station within 5 minutes, then your time starts again as soon as you pass through the timing station. If you have not passed through the timing station when the five minutes is up, then your time will start again automatically. The distance between the two timing stations is 1km, which should take approximately 3 minutes to complete at non race pace.

You are not Racing between the Oval Timing Station and the Camden Street Timing Station.

So, whether you linger for just a couple of minutes or take your time to get a bite to eat or drink, is up to you. At the Oval you’ll find a water station, feed station plus a coffee van and food/drinks stall (all proceeds to Wingello School). There is also a shop on the south side of the railway crossing.

Camden Street Timing Station: Full Flingers, Flinging Threesomes, 100mile Flingers

This is the start and finish point for the Shimano Stage.

shimanoShimano Stage (50km. Start cut off time:11.30am): Full Flingers, Flinging Threesomes, 100mile Flingers (Two laps. Second lap start cut off time:1.30pm)

After just a couple of kilometres of dirt road, the Shimano Stage 2 takes you in a big loop around the perimeter of Wingello State Forest. Keeping primarily to native forest sections, you’ll enjoy both scenic and challenging riding. This includes the superb network of singletrack – The Great Wall, Love Love Love, Send in the Clowns and Dailemma, Flinging Scotsman, Tangles and Princess’ Revenge! Rough forest trails interspersed with faster tracks provide you with plenty of variety. You will descend into numerous gullies and will surely be feeling the climbs back out by the time you reach Halfway Hill (which is actually at about 62km – well over halfway – it’s a historical thing!). Some say Halfway Hill is the big down to the lowest point on the course.  Others claim it to be the climb out.  Let it be where you want it to be … Down and up you go and do the same again on The Kick. Once out of the basin the forest tracks allow for some fast progress, with occasional views across to the depths of the Shoalhaven Gorge in the Wild West, and on to the Outer Limits. The tracks roughen up a touch for the climb out to Bumballas Road. Then you’ll get a chance to spin the legs along the well-graded dirt back to Wingello. There’s a Feed Station, the Frequent Riders Lounge, about 29km into the Shimano Stage. But don’t hang around too long at the Lounge – there is a cutoff time here of 1.30pm for Full Flingers.

You will again pass through Camden Street timing station, at which point your time will pause for a period of up to 5 minutes. You should make your way safely back to Bill O’Reilly Oval and to the next timing station. Again, the distance between the two is 1km, approximately 3 minutes’ ride at non race pace. Many will appreciate the break and take longer to refuel for the final push on the GU Stage to the finish line.

Note that the two timing pauses are completely independent of each other, i.e. you can take a maximum of one 5 minute timing pause at each occasion rather than one 10 minute total pause over the two occasions. Therefore, taking 7 minutes at the second stop will still mean that your time starts automatically after 5 minutes, even if you only took 3 minutes at the first stop.

GUGU Stage (31km. Start cut off time:3.30pm): Full Flingers, Flinging Threesomes, Half a Fling, Some Flingers (part) 100mile Flingers (start cutoff time 4.00pm)

Spin the legs for several kilometres of flat dirt road before a sharp turn into private property. Rapidly alternating sections of single track and farm roads before a fast paddock run down to Paddy’s River. Ride uphill along Jack’s Jaunt, a lovely section of singletrack through the gums, before a quick return through Penrose SF. All too soon you’ll be cleaning your bike again before following the wheel tracks of the Some Flingers who enjoyed the singletrack of Boundary Rider earlier. Book your ride on the Rollercoaster, before winding along the river to Flatrock Crossing and up the hill to enter Sherwood Forest. A winding route of singletrack, farm track and paddock trail leads through Jim’s Joke, up Brokeback Mountain and down through Lawyer’s Lament. Don’t cook yourself in Baker’s Delight or Double Rubble before you end up out on the Great Sandy Desert with 8km to go. Decision time at Your Call awaits – go left for shorter and steeper, right for longer and leveller … decisions, decisions. Out onto a dirt road where The End is Nigh with 3km to go.  But before you finish, there’s one last winding section of farm tracks to sap whatever energy you have left!

Then it’s over, and you can say you’ve had your Fling!

Event Map_Wingello

Wingello Oval Transition Area Map

The 100mile Fling

The 100Mile Flingers will do the Ground Effect Stage followed by 2 loops of the Shimano Stage before completing the final GU Stage (to huge applause and respect!). The race is aimed at Endurance riders with the ability to complete such a challenge within approximately 9.5 hours. There will be cut off times at 80km (end of first Shimano loop 1.30pm) and 133km (end of second Shimano loop – 4.00pm). Any rider arriving after these times will not be allowed to continue to the finish. 100Milers who transfer to the Full Fling part way through the race will receive a time but will not receive a category place.