Tasmania 3 Day Itinerary – The Convict Trail


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Visitors who are keen on history and looking for things to do in Tasmania with a focus on the island’s rich past, a Tasmania 3 Day Itinerary from Hobart to Port Arthur is a great way to explore.

The convict trail passes through the town of Richmond, which is one of the prettiest places in Tasmania.

It drops south, through the former grain town of Sorell – which has its own collection of prized 19th-century buildings – and Dunalley, a small fishing village.

The A9 road then stretches out over Eaglehawk Neck, a 100-metre wide isthmus that connects mainland Tasmania with the Tasman Peninsula.

There are some stunning natural sights in this vicinity, with a series of blowholes, cave formations and sweeping cliff-edge views.

Tasmania 3 Day Itinerary
Eaglehawk Neck Beach on the way to Port Arthur while following a Tasmania 3 Day Itinerary. Photo: Andrew McIntosh, Ocean Photography

Tasmania 3 Day Itinerary

Day 1 – Hobart

Wandering around Hobart’s waterfront, Salamanca and Battery Point will put you in the mood for a history tour.

Check out the Female Factory, which is at the base of Mt Wellington too. Here are 30 things to do in Hobart.

Day 2 – Richmond

Richmond’s history

Tasmania 3 Day Itinerary
Tasmania 3 Day Itinerary for history lovers – Historic Richmond Village. Photo: Brian Dullaghan

Founded in the early 19th century, 27km north of the Tasmanian capital, it’s part of the so-called ‘convict trail’, which snakes up from Hobart and down to the rugged Tasman Peninsula, where nestles the penal site of Port Arthur – one of Tasmania’s most visited tourist attractions.

Initially, a small farming community, Richmond transformed into a key military post and prison station after the construction of a bridge that linked Hobart with the east coast of Van Diemen’s Land (as Tassie used to be known) in 1823.

Neer-do-wells comprised much of the early population, although the area – under the authority of the strict Lieutenant-Governor, George Arthur – soon attracted free settlers, with publicans, blacksmiths, wheelwrights, saddlers and tanners setting up businesses here, sparking Richmond’s growth from village to town.

The boom ended after the 1872 opening of the Sorrell Causeway, which went from east to west and bypassed Richmond.

Shorn of its strategic importance, and with Port Arthur becoming the region’s dominant prison site, Richmond remoulded itself back into a small rural community, albeit one that is keen to showcase its significant heritage to tourists.

Richmond vibe

Tasmania 3 Day Itinerary
Ducks at historic Richmond Bridge on a Tasmania 3 Day Itinerary.

Trying to enjoy a nice picnic by the river isn’t easy when you’ve got pesky little yobs raging around threatening to steal your ham sandwiches.

It’s a type of anti-social behaviour you don’t really expect to endure when you roll into Richmond, Tasmania’s most quintessentially genteel English-style village.

But ducks will be ducks.

Around 50 of the blighters, of varying colours, shapes and sizes, are frenetically patrolling the grassy banks of the Coal River, making a cacophony of noise and generally annoying everyone in sight.

Two ducks, in particular, are acting like schoolyard bullies, terrorising a small, taciturn web-footed neighbour to breaking point.

One of the brutes has pinned down his victim and is now treading on his back, while his partner in crime stands upright, surveying the area like a burly doorman and making sure no-one intervenes.

Perhaps I shouldn’t be surprised by this thuggery because, for all its undoubted beauty and tranquil nature, Richmond has a history of rebellious residents.

What to see in Richmond

Tasmania 3 Day Itinerary
Tasmania 3 Day Itinerary- Richmond Bridge. Photo: Scott Spoleder

Walking around Richmond today, it’s no surprise that many consider this the most charming place in Tassie.

The town’s iconic sight is the convict-built bridge, which is the oldest of its type in Australia and still looks picture perfect as it reflects into the river below – despite those irascible ducks doing their best to misbehave.

In the background are:

  • St John’s Church (built in 1836), the country’s first Catholic place of worship
  • St Luke’s Anglican Church, Richmond courthouse (1825)
  • the old post office (1826)
  • the Richmond Arms Hotel (1888)
  • the Richmond Gaol (1825), which was built five years before Port Arthur opened its gates, and has been remarkably well preserved. Visitors can peruse the gaol’s solitary confinement and punishment cells.

A raft of delightful old Georgian cottages and manors line Richmond’s main thoroughfare, Bridge Street, and there are a handful of B&Bs, neat cafes, arts and craft galleries and boutique shops.

Tasmania 3 Day Itinerary
Tasmania 3 Day Itinerary

Further along is Old Hobart Town, a model village depicting Hobart in the 1820s.

Recreated from the city’s original plans, it’s both authentic and informative and also makes you feel ten feet tall.

Next door is the wooden-walled Richmond Maze, where children love getting lost while the oldies relax in the adjoining tea rooms.

Anyone wanting to dig deeper into Richmond’s history can enjoy guided walks through town, or even a horse-drawn carriage ride.

Day 3- Port Arthur

If ever a place encapsulated the beautifully-haunting nature of Tasmania, it’s Port Arthur; a site brimming with both sumptuous scenery and dark tales of the past.

Port Arthur Historic Site

Tasmania 3 Day Itinerary
Tasmania 3 Day Itinerary – Port Arthur Historic Site. Photo: Stuart Crossett

Old prisons are supposed to be grotty, dirty and inhospitable. Yet, with its delightfully green surroundings and elegant Georgian architecture, Port Arthur is anything but.

However, lurking beneath the verdant setting are tales of grim-faced horror that stretch back to when Tasmania – or Van Diemen’s Land – was a dumping ground for some of the most hardened British criminals.

The penitentiary was, according to English prison reformer Jeremy Bentham, ‘a machine to grind rogues honest’, and its tools were discipline and punishment, religious and moral instruction and training and education.

Prisoners were also forced to work in local mines (the Coal Mines Historic Site is a 25 minutes’ drive from Port Arthur, near Saltwater River on the northwestern tip of the Tasman Peninsula).

Port Arthur was dubbed an ‘escape proof’ gaol upon its opening in 1830. Naturally, several inmates tested the validity of this theory over its 47 years of existence.

Those who did survive and were recaptured maybe wished they hadn’t, such was the horrific nature of sentences meted out; for instance, would you prefer to be flogged to within an inch of your life, or kept in solitary, dark and silent confinement for 23 hours a day?

When you hear all this – and you hear plenty of stories on the excellent guided tours – it’s hardly a shock to discover the authorities had to ultimately build an asylum on site.

Port Arthur history

As you explore Port Arthur, you’ll struggle not to admire the buildings that the convicts built, although some are little more than ruins these days.

More than once you’ll probably wonder if all those grim tales are really true, such is the bucolic, kindly calmness of this place.

Port Arthur was reintroduced to tragedy in 1996 when a lone Hobart gunman went on a killing spree at the site’s Broad Arrow Cafe, murdering 35 people and wounding several more.

A memorial garden was established round the shell of the cafe that was gutted following the massacre.

Fittingly, it’s eerily silent.

Port Arthur ghost tour

When nightfall arrives, Port Arthur takes on a different character and the best way to exploit this is by joining the popular lantern-lit ghost tours, where you’re told creepy tales about the site’s past – and present.

It’s a touch contrived at times – there are plenty of cliched moments involving slamming doors and dark shadows – but it’s good fun nonetheless.

Actually, I say, it’s fun, but it makes the drive back to Hobart a little unnerving.

Add a dark, winding road with rogue wildlife hopping in front of you – kangaroos and wallabies – and the feeling that someone – or something – is breathing on the back of your neck, and you’re rather on edge.

And I can’t help but think: it must have been hell trying to escape from Port Arthur at night.

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Tasmania 3 Day Itinerary – The Convict Trail

Tasmania 3 Day Itinerary – The Convict Trail

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I'm a freelance travel writer, journalist and photographer who suffers from a severe - and probably incurable - case of wanderlust. After getting a 2:1 BA (Hons) multi-media journalism degree on the (occasionally) sunny south coast of England, I spent six years honing my trade in regional newspapers - in news and sport, writing and subbing - before embarking on an incredibly life-changing round-the-world trip in 2005. Since this adventure - which included stints living and working in Perth and Sydney and doing the classic backpacking trail up the Australian east coast - I haven't had a 'real job' as such. But I have visited, photographed and written about over 80 countries across Europe, the Caribbean, the Americas, Asia, Africa and Oceania, contributing to dozens of publications, both print and online, in the UK, Australia, New Zealand and the USA. Outlets include the Sydney Morning Herald, Sydney Sun-Herald, Virgin Voyeur, Travel & Living, the West Australian, International Traveller, Vacations & Travel, New Zealand Herald, ninemsn travel, Sunday Times (UK) and the Daily and Sunday Express (UK).


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