On alighting the bus from Dublin, cross the road and turn right to reach the walk start point in front of an old castellated arch containing some old gates. These gates lead to the Rathfarnham Old Church and Cemetery (contact Dublin City Council for information on gate opening times). Near the entrance to the graveyard, to your left, is the tomb of yet another noted rebel, Captain James Kelly. Nicknamed ‘the Knight of Glendoo’, Kelly was a local leader of the Fenian Rising of 1867. The Fenians, like so many Irish rebel movements, hoped to trigger a general insurrection all over Ireland (and overseas – they even tried to invade Canada from the US) but were quickly quelled. Captain Kelly, however, escaped serious British retribution and lived until his 70th year, dying in 1915.

Facing the gates, walk left and continue south on Rathfarnham Road to Main Street. Walk south on Main Street passing on your way a distinctive small building on the left that is now the home of Rathfarnham Athletic Club. This is Rathfarnham’s Old Courthouse, in fact the ‘Court of Petty Sessions’, erected in 1912.

Turn left again, cross Rathfarnham Road and enter Rathfarnham Castle, which stands just north of the corner of Rathfarnham Road and Grange Road. In front of you is a sturdy, white-painted building that looks part mansion, part fortress. Rathfarnham Castle was built around 1583 for Adam Loftus, the Yorkshireman who became Anglican Archbishop of Dublin and Lord Chancellor of Ireland. With Spain supporting Irish lords in rebellion against English rule, Loftus clearly felt the need for a home that could be easily defended. He took out an extra insurance policy too: secret tunnels led from the castle cellars to exits in what is now Rathfarnham Golf Club’s Castle Course, and to the village churchyard, so that if the defences failed the castle’s inmates still had a chance to escape. Sadly, both tunnels are now bricked up. At the outbreak of the English Civil War, Rathfarnham was besieged by Irish rebels in 1641 and garrisoned by English Parliamentary troops in the following year, when the Parliamentarian leader Oliver Cromwell is said to have stayed here before sending his troops to carry out the notorious massacres of Irish soldiers and civilians at Wexford and Drogheda. The castle remained in Loftus hands until 1724, when a dissolute descendant, Philip, Earl of Wharton, sold it to pay his debts. The buyer was the Right Honourable William Connolly, MP, Speaker of the House of Commons – and a founder member of the notorious Hell Fire Club. Legend has it that this group of rakes, drunks and ‘bucks’ would meet at the hunting lodge that Connolly had built in the Dublin Mountains above Rathfarnham to drink, debauch, and hold black Masses to summon up the Devil. There doesn’t seem to be much truth in this – the Hell Fire Club did exist, and Connolly was associated with it, but its members seem to have done most of their misbehaving in the Eagle Tavern on Cork Hill, beside Dublin Castle. But one gruesome find hints at skulduggery at Rathfarnham too. In 1880 builders discovered the skeleton of a young woman in a hidden chamber in the hollow walls of the building’s first floor. An inquest determined that the cadaver had been there for more than 130 years. Legend has it that she was locked into the secret room while two rivals fought a duel for her hand in marriage. The survivor was to release her; unfortunately, they killed each other and she was left to die of hunger and thirst. In 1912, property developers Bailey and Gibson bought the castle and built houses over most of the grounds and turned the remaining open space into a golf course. Delaware Properties, which bought the property in 1985, planned to demolish it but after a public campaign it was acquired by Heritage Ireland, which is gradually restoring different sections. Inside, the most striking parts are the finely proportioned rooms and halls designed by two great Scottish architects, Sir William Chambers and James ‘Athenian’ Stuart. 

Leave the castle where you entered on Grange Road, turn left and walk for 400m (437 yards). At the junction with Nutgrove Avenue, Grange Road turns sharply to the right. Follow it to the gates of the former Loreto Abbey on the left. Originally called Rathfarnham House, this massive Georgian pile was built in 1725 for William Palliser, a wealthy Yorkshireman who made his fortune in the arms industry before moving to Ireland to built a palatial home, where he entertained guests including Handel, Jonathan Swift and the poet Thomas Moore. There’s a story that at one soirée the guests locked Moore in one of the rooms and refused to let him out until he had composed a lyrical piece for them. The result was his most famous air, Oft in the Stilly Night. In 1821 the Catholic archbishop of Dublin, Dr Daniel Murray, bought the house in order to set up a religious school for girls. It eventually spawned 22 daughter-convents as far afield as Australia, Africa and Mauritius. Its most famous pupil is Mother Teresa of Calcutta (1910–97), who enrolled here in 1928 at the age of 18, taking the name of Loreto’s first Mother Superior. Loreto finally closed in 1999. However, this historic building is once again to be filled with children studying – the building has been acquired by the Department of Education and there are plans to establish an Irish language school here. Peer through the imposing gates for a glimpse of the beautiful building.

Continue past the Abbey Gates on Grange Road. After passing Barton Drive and Barton Road West on your left, cross to the west side of Grange Road and enter St Enda’s Park. Walk south to the Pearse Museum. Padraig Pearse (1879–1916) set up St Enda’s School for Boys here in 1908 to educate boys in the Irish language. A fervent nationalist, Pearse believed the national language – which was rapidly dying out by the early 20th century – was essential to building a national identity. In 1913 he became a member of the secret, radical Irish Republican Brotherhood and was soon one of its leaders. He seems to have had a bloodthirsty, mystical streak; writing about the battles of World War I in 1915, he spoke of ‘the old heart of the earth’ needing to ‘be warmed with the red wine of the battlefields’. Blood sacrifice in the nationalist cause is a common theme of his speeches and writings, and it was this that led him to march the 5 miles (8km) from Rathfarnham to the General Post Office in Dublin to proclaim the Irish Republic on 24 April 1916, beginning the Easter Rising. Six days later, Pearse and his comrades surrendered to the British. On 3 May, after a summary court martial, he and 14 others, including his younger brother Willie, were executed in Kilmainham Gaol. When you are ready to return to central Dublin, walk back to Grange Road and take bus No. 16 back to the city centre.