4.8km Calton Hill and Hidden Gems Walk

View of Calton Hill and its Monuments

4.8km Calton Hill and Hidden Gems Walk

This route takes you to some of the hidden gems of the Edinburgh City Centre, some with a dark history. See the city from Calton Hill, learn about a beloved army bear, and learn how to avoid another Great Recession. The route can start at either point, as they are near the easily accessible Princes Street.

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Route overview of the 4.8km Calton Hill and Hidden Gems Walk

Route overview

Our route starts at the Wojtek Soldier Bear Memorial in Princes Street Gardens. As you enter the gardens, follow the path closest to the main road.

The Wojtek the Soldier Bear Memorial commemorates the bear that served in the Polish military during WWII. Wojtek was adopted by Polish soldiers around 1943 in Iran. The bear cub quickly became a favourite amongst the soldiers and served as a booster for their morale. By the next battle, the fully grown bear was already very hands-on, helping to carry supplies and saluting. He particularly enjoyed swimming, eating cigarettes, drinking beer, and wrestling with the soldiers (of course).

In order to get around the dilemma of bringing the bear along with them in battle, the soldiers gave him the title of “Private Wojtek,” which translates to “joyful warrior” in Polish, in the 22nd Artillery Transport Company. Wojtek continued to help the soldiers using his own paws like a person moving ammunition crates, so much so that a picture of him carrying an artillery shell was adopted as the official emblem of the 22nd Company. Wojtek was relocated to the Edinburgh Zoo in 1947 following the demobilisation of the 22nd Company. Over the rest of his life, he received several visits from his new fans in addition to his old Polish brothers-in-arms. At the age of 22, he passed away in 1963.

Wotjek the Bear Soldier in Princes Street Gardens

Wojtek the Bear Soldier. Credit: Expats Poland

Exit the park using the entrance closest to the statue and walk towards the Scott Monument. Continue for about 500 metres until you see the sign for Calton Hill steps on your left.

Part 1 of the 4.8km Calton Hill and Hidden Gems Walk from Princes Street Wojtek Bear statue to Calton Hill

Part 1 of the 4.8km Calton Hill and Hidden Gems Walk

There is probably nowhere in the city that offers a more picturesque perspective of the surrounding area than Calton Hill. Scattered around the hill are structures and monuments such as the City Observatory, the Nelson Monument, and the National Monument. The National Monument honours the Scottish sailors and soldiers who fought in the Napoleonic Wars and was designed to mimic the Parthenon in Athens. But because of a lack of funding, it was never completed, and in true Scottish style, it earned the nicknames “Edinburgh’s Disgrace” and “Scotland’s Folly” as a result. Between the pillars, you will probably discover many individuals posing for pictures.

View of Calton Hill and its Monuments

View of Calton Hill and its Monuments. Credit: Parliament House Hotel

Exit Calton Hill at the same steps. Turn right, then right again to go down Caalton Hill Road, then left on Calton Road to go under a bridge.

Part 2 of the 4.8km Calton Hill and Hidden Gems Walk from Princes Street Wojtek Bear statue to Calton Hill

Part 2 of the 4.8km Calton Hill and Hidden Gems Walk

Just after a second bridge, turn right onto Old Tolbooth Wynd, where you will see the Tolbooth Tavern after going through the tunnel.

Part 3 of the 4.8km Calton Hill and Hidden Gems Walk from Calton Hill to Tolbooth Tavern

Part 3 of the 4.8km Calton Hill and Hidden Gems Walk

The Tolbooth Tavern was constructed in 1591 and served as a tollbooth for those wishing to enter the city. It also served as a council chamber, a police court, and a prison. Nearly 230 years later, in 1820, this building became the drinking spot of choice in Canongate. Canongate got its name from the fact that metal artillery was forged here for Edinburgh Castle.

The clock tower was a later addition in 1884, with symbols of King David I and Holyrood. Naturally, a building so old is assumed to have some ghostly visitors. Reports of items falling and being moved around have been reported. But no one quite knows who these ghostly visitors are. You can see their website here for their menu and opening times.

Tolbooth Tavern

Tolbooth Tavern. Credit: Open Table

Walk through Bakehouse Close, passing the small car park, then go down the stairs on the right, and continue down Hammermen’s Entry to turn right into Holyrood Road.

Part 4 of the 4.8km Calton Hill and Hidden Gems Walk from Calton Hill to Tolbooth Tavern

Part 4 of the 4.8km Calton Hill and Hidden Gems Walk

Holyrood Road becomes Cowgate. Just after walking under South Bridge, turn left through Hastie’s Close, right to continue, then left down Guthrie Street. Turn right on Chambers Street. At the end of the road, at the National Museum of Scotland, turn left to find Greyfriars Kirkyard on your right. Exiting the Kirkyard where you entered, turn left, passing Greyfriars Bobby Bar. At the roundabout, turn right to find Magdalen Chapel on your right.

Part 5 of the 4.8km Calton Hill and Hidden Gems Walk from Tolbooth Tavern to Greyfriar's Kirkyard and Magdalen Chapel

Part 5 of the 4.8km Calton Hill and Hidden Gems Walk

Edinburgh has a history of body-snatching. The act of robbing a grave for a dead body to sell or dissect by an anatomist or for research at medical schools. Two grave robbers, in particular, are well-known: William Burke and William Hare. Due to the scarcity of cadavers for medical research, Burke and Hare used to lure their victims (lodgers) and murder them.

They were then sold to Dr. Robert Knox. This became so common and so much of a concern that cage-like tombs, called mortsafes, were built to prevent it. These mortsafes varied in design, from iron cages to stone table tombstones or concrete boxes. It was not until 1832 that obtaining cadavers legally and ethically was made possible by the Anatomy Act. You can see two examples of these mortsafes to the left of the church, near the statue of “Bobby.”

Mortsafe at Greyfriar's Kirkyard

Mortsafe at Greyfriars Kirkyard. Credit: Colin Gould

At the back left-hand wall of Greyfriars Kirkyard, by the main gates, you’ll find the George Mackenzie Mausoleum. Entrance to the interior is possible through a booking with the City of the Dead Haunted Graveyard Tour.¬†Religious conflict escalated in 17th-century Scotland following King Charles’ introduction of the Common Book of Prayer, and he declared opposition to it treasonous.

George Mackenzie was the persecutor of the Covenanters, who opposed the Book of Prayer and supported the Presbyterian church. A barrister and Lord Advocate who earned himself the nickname “Bluidy Mackenzie” due to his harsh and brutal punishments. Covenanters were held captive by him in a part of this graveyard, where they endured cruel treatment before having their heads displayed on the spiked gates.

Somewhat ironically, Mackenzie is now buried in the very same cemetery where he tortured offenders. Over the years, much vandalism has taken place at this mausoleum, including a homeless man falling through the floor in 1999 (you can still see the hole through which he fell), and in 2004, unidentified remains were removed by a couple of teens who even used a skull as a puppet… It is rumoured that there is some ghostly activity, with incidents including bruises and scratches.

Mackenzie Mausoleum in Greyfriar's Kirkyard

Mackenzie Mausoleum. Credit: Forever Edinburgh

Magdalen Chapel is easy to pass by without giving it a second thought. However, there’s a particularly unique feature within. During the Scottish Reformation, much religious art was destroyed, removed, and replaced with simpler adornments. But this chapel has the only surviving stained glass from the Scottish Reformation in its original location. The central window has four stained glass shields, including a representation of the Royal Arms of Scotland and those of Mary of Guise, mother to Mary Queen of Scots. The chapel was built in 1541 for a trade guild, and academic lectures were held here in the years leading up to the Reformation. See their website to confirm visiting hours.

Magdalen Chapel Stained Glass Window

Magdalen Chapel Stained Glass Window. Credit: AlasdairW, Wikimedia Commons

Leaving the chapel, return to the roundabout and continue straight onto Cowgatehead towards Grassmarket. At the end of Grassmarket, turn right onto King’s Stables Road and follow the road alongside Edinburgh Castle. The road is a bit of an uphill so get ready.

Part 6 of the 4.8km Calton Hill and Hidden Gems Walk past the Edinburgh Castle

Part 6 of the 4.8km Calton Hill and Hidden Gems Walk

When you reach the main road, turn right on Lothian Road. At the intersection, cross over where it’s safe to turn into Queensferry Street, passing the Johnnie Walker store. Continue along Queensferry Street. After 320 metres, turn left into Drumsheugh Gardens, then left onto Melville Street Lane, following the curve to reach the Library of Mistakes.

Part 7 of the 4.8km Calton Hill and Hidden Gems Walk to the Library of Mistakes

Part 7 of the 4.8km Calton Hill and Hidden Gems Walk

The Library of Mistakes is exactly that. Specifically, books on economics and finances so as to (hopefully) avoid another financial catastrophe like that of the 1929 and 2008 Great Recessions. Books by Karl Marx, Milton Friedman, Paul Krugman, and Michael Lewis are included in the collection of over 2000, which covers every country in the world. The principal purpose of the library is to provide literature that enables future economists to look back and gain insight into the flawed algorithms and assumptions that economics and economists have used and applied in theory, thus avoiding history repeating itself. See their website to register and visit for free.

Interior of the Library of Mistakes

Interior of the Library of Mistakes. Credit: Library of Mistakes Website

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If you enjoyed this route, see our UNESCO City of Literature Walk.

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