Loughglynn is in the heart of the west Roscommon Lake District and is and area rich in history and folklore.
Loughglynn is part of the ancestral home of the Costelloe clan and the village is one of the stages of the 'Beara-Breifne Greenway' which is based on the historic march of O'Sullivan Beara in 1603.
Loughglynn House was built by Richard, 9th Viscount Dillon, between 1713 and 1737. It was typical of the type of mansion built following the Williamite Wars - Palladian in style and originally it had a Mansard roof (four double-sloped sides). The house was extended in the 1820s and altered again in the early 20th century. Loughglynn House was recorded in 1814, 1837, and in Griffith's Valuation as the seat of Viscount Dillon. A demesne of 80 acres of woodland was planted around Loughglynn House in 1801. The top storey of the house had to be replaced after a fire in 1896.
The Dillons became absentee landlords in the mid eighteenth century, when the Eleventh Viscount Dillon married an English heiress. For much of the nineteenth century a number of land agents administered the estate, the most notable were Jerrard Strickland and his son Charles. In 1872, Charles Strickland lived at Loughglynn House and he was responsible for building the town of Charlestown and he also built a large part of Ballaghaderreen.
In 1903 the house was sold to the Bishop of Elphin, Dr Clancy, and acquired shortly afterwards by the Franciscan Missionaries of Mary, who established a convent there and started a school where teenage girls would learn Home Economics. The sisters also founded a dairy which provided employment and training for a large number of local people, and Loughglynn butter and cheese became famous all over the world. The dairy closed in the 1960s and the sisters then opened a nursing home for their own retired sisters and some elderly residents from the locality. The convent was sold in 2003 and fell into private ownership.
Located on the southern side of Loughglynn, among the woods, is the remains of a Norman castle of that name, said to have been founded by the Fitzgeralds of Mayo. The castle was defended at each angle by a tower, one of which in later times, was used as a temporary prison. One last remaining tower of the castle still stands.
Close to the village of Loughglynn is the site of the 1921 Loughglynn Ambush. On April 19th, 1921 four IRA men were hiding in a house near Loughglynn wood and they attempted to escape when they learned that the Black and Tans were combing the wood. Two of the men, Joe Satchwell and Thomas (Toby) Scally, were wounded. Following a 'drumhead court martial' (court martial held in the field) the other two, Sean Bergin and Stephen McDermott, were shot on the spot. It is about this ambush that the well-known song 'The Woodlands of Loughglynn' was written.
Edward (Ned) Duffy, chief organiser of the Fenian Movement in Connaught (1862 - 1867), was a native of the Loughglynn / Ballaghaderreen area. His activities in the Fenian movement included recruiting new members, organisation and training, distribution of the 'Irish People', and classes in Fenian dogma. Duffy was arrested at O'Leary's hotel in Boyle, County Roscommon on March 9th 1867. He was tried in May 1867 and convicted to 15 years penal servitude at Millbank prison, London, where he died on January 17th 1868. On hearing of his death, O'Donovan Rossa wrote a poem which includes the lines:-
"In the dead house you are lying Ned and I'd wake you if I could. But they'll 'wake' you in Loughglynn Ned, In the cottage by the wood."
Two of Duffy's sisters taught in a cottage near where the monument now stands.