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Shadows of the Past: The Midlands Silhouette Trail

  • Shadows of the past, Heritage Highway. Image Credit: Darren Wright

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Shadows of the Past: The Midlands Silhouette Trail

When travelling through the Southern Midlands, play a game of Eye Spy: The Silhouette Trail edition!

As you cruise south through the Southern Midlands between Tunbridge and Kempton, keep your eyes peeled — there are shadowy characters lurking along the roadside. Play a game of Eye Spy: Silhouette Trail edition!

The sixteen sculptures dotted along the roadside and up on hilltops between Tunbridge and Kempton serve as poignant reminders of early colonial life on the Heritage Highway. The project was initiated by local artists Folko Kooper and Maureen Craig, and informed by the meticulous records kept by colonial authorities. The silhouettes bring the stories of this intriguing region to life.

It’s worth pausing to note that those records were kept by colonial authorities — and they tell only one side of the story. The palawa people of Tasmania were here long before the first ship arrived, and their connection to this land continues today. The silhouettes capture a moment in history, but history here runs far deeper.

The troop of soldiers at St Peters Pass reminds us that Van Diemen’s Land was first and foremost a British military outpost, while the professional hangman silhouette south of the Stonor turn-off might give you the willies!

Could it be Hangman Solomon Blay, who dispatched his ‘clients’ with speed and efficiency?

Execution was intended to be a deterrent, with hangings carried out in public until the middle of the 19th century. While hangings in Britain were often more like carnivals, they were a more solemn affair in the colonies, the crowd would often sing in solidarity with the condemned as they met their fate.

Keep an eye out for the poor chain gang hard at work on the hill north of the York Plains turn-off. The chain gang was a cruel and painful 1826 colonial innovation designed to break the spirit of those who were insolent or questioned authority.

Shadows of the Past. Image Credit: Darren Wright
Shadows of the Past. Image Credit: Darren Wright

Some convicts chose to be bushrangers because they thought it better than the chain gang — and south of Oatlands, a lone bushranger silhouette crouches against the skyline to prove the point. Figures like Michael Howe (‘Governor of the Woods’) and Matthew Brady became legends in their own time, but their freedom was rarely long-lived. Other convicts took advantage of the rewards and pardons offered for hunting down bushrangers, so it was a dog-eat-dog world!

Did you know there was actually a Tasmanian emu?! The emu silhouette south of Tunbridge hints that this is more than just a myth.

The creatures ran wild across the state until early settlers hunted them to near-extinction by the 1830s. 

The last known examples were in captivity; when the final birds from a breeding program drowned crossing a flooded river in 1873, the Tasmanian emu was gone for good. 

Keep an eye out for the 20th century’s victim, the poor Tasmanian Tiger, with silhouettes north of the Stonor turn-off. (Or are they still out there, deep in the bush?)

Shadows of the Past.

By the time you reach Kempton, the pace picks up, literally. Three stagecoach silhouettes mark the end of the trail, a nod to the fierce coaching competition that shaped the Midlands in the 1840s and 50s. Rival operators raced each other, prices plummeted, and horses were pushed to their limits, it was the road-rage era of the 19th century.

If these highlights have you hooked, there’s plenty more folklore to discover! Check out Shadows of the Past for the stories behind all 16 silhouettes and a map of the Silhouette Trail.

Picture of Hobart and Beyond Editorial Team

Hobart and Beyond Editorial Team

The Hobart and Beyond Editorial Team is dedicated to bringing you the best insider tips, local stories, and up-to-date guides to exploring southern Tasmania.

Article Details:

Article Created: 23 October 2023
Last Update: 16 April 2026
Author: Darren Wright
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