Swap city streets for sandstone culverts, convict carvings and bush solitude on this legendary mountain bike ride from Wisemans Ferry.

If you’re after a bike trail that feels bigger than the pedals beneath you, the Old Great North Road bike ride delivers. Set in Dharug National Park in the Central Coast region, this is no ordinary spin through the bush. The 86-kilometre return route traces part of a convict-built road from the 1820s, now protected as one of the UNESCO World Heritage-listed Australian Convict Sites.

As you pedal upwards, the story of the past reveals itself. Enormous buttresses rise along the roadside, culverts tunnel beneath the track and sandstone walls stand as silent witnesses to an era when labourers toiled with chains and picks. It’s a ride through history as much as through wilderness.

How hard is it?

Make no mistake, this is not a gentle spin through the bush. The Old Great North Road bike ride is rated hard, and with good reason. Steep climbs demand stamina, rocky sections test balance and the sheer scale of the ride requires preparation. The full return can take up to two days, and water along the way must be boiled or treated before drinking.

For those not ready to take on the whole stretch, shorter options make the experience more accessible. Many riders turn around at Ten Mile Hollow campground, about halfway along, or take on the 28-kilometre Devines Hill loop, a circuit that still packs in impressive stonework and wide views without the full commitment.

What you’ll see

What sets this ride apart is the combination of challenge and atmosphere. There are moments of true solitude, where the bush closes in and the only sounds are your tyres crunching over gravel and the calls of birds. Then, just as suddenly, the landscape opens up to reveal sweeping views across the Hawkesbury. The mix of natural beauty and built heritage makes it one of the most rewarding rides in NSW.

Tips for your ride

Start at Wisemans Ferry and follow signs to the trailhead.

Carry water and food – there are tanks along the way, but you’ll need to treat or boil any water.

Allow time – a full return ride can take up to two days.

Look after the heritage – some fragile sections request that you walk your bike to protect the stonework.

If cycling isn’t your thing

If tackling the trail on two wheels feels daunting, there’s another way to experience its history. The Old Great North Road World Heritage walk is a nine-kilometre loop that takes around four hours on foot. It leads through many of the same engineering feats and scenic outlooks, offering a more contemplative way to step back in time without the same intense burn in your legs.