Bailieborough, like its neighbouring town Virginia and the other American Virginia has its origins in the plantation of Ulster. William Bailie, a Scottish "undertaker" or Planter, was granted the lands of Tonergie (Tandragee) in East Breffnie, by James I of England. He built a castle and enclosed the demesne by 1629. On his death the estate passed to his son, William, Bishop of Clonfert. The Bishop's daughter married James Hamilton and on the Bishop's death they inherited Bailieborough Castle. Henry Hamilton, their son, was a member of the IRA, but died at the Siege of Limerick in 1689.

• Market House
  We can now begin our tour of the town with a look at the attractively restored Romanesque style Market House. Built in 1818 by Colonel Young, it replaced an older building, which stood in the middle of the Main Street between O'Reilly's and the National Irish Bank, built approx. in 1789. The upper room, which runs the whole length of the building was used for concerts, travelling cinema, theatrical performances and meetings. Today it is still used for small community groupings and art activities. The ground floor was used for trading on market days and the town weighbridge was controlled from the building, weighing local produce e.g. oats, potatoes and turnips. Since the days of the market the building has served as a fruit canning factory and then lay dormant due to fire damage. In 1980, Bailieborough Co-Operative restored the building using it as a hardware shop. In 1988, it was bought by Cavan County Council which now houses an extensive library.
  
  
• Masonic Hall
  The Masonic Hall building was completed in 1878. Originally this was the site of the Presbyterian Institute for the education of boys in the faith. This fell into disuse in the 1880's and came into the possession of the Masonic Order. During the World War II Emergency, it was taken over by the Irish Army, but reverted back to use by the Masonic Lodge. The formation of the Bailieborough Masons Lodge number 796 dates from 1794. It is still a meeting place for the Masons of the area.
  
  
• Bexcourt House
  Originally built as an army barracks in 1798. The grounds of the then barracks were used to intern 1798 rebels and United Irishmen from the local battle of Rebel Hill. In 1807 the building became the Rectory, spelled as Beek’s Court, for the parish of Mullagh alias Killinkere. It’s reverend residents included Rev. Arnold Cosby (1812) and Rev. Mahaffy, (1817). The land in front of Beek’s Court House “Cahill’s meadow” was used for a period by the Bailieborough Shamrock’s GAA Club as a Gaelic football pitch. Returning back to Main Street, you walk up the hill through Thomas Street. Here in 1875, a school for poor children was opened and known locally as the ragged school
  
  
• James Family Home Place
  As we walk down the Main Street the National Irish Bank is on our right and across the street O'Reilly's shop, between these two buildings was the site of the original Market House and Square and this explains the open space in front of the shops and bank. After Moynagh's shop, the adjoining private residence is a house of note. This building was the business and home location of the James Family. In 1856, Henry James great grandson of James of Curkish had a shop here, and followed later by Jane James who had a drapery shop. The home of the James' was Curkish (out the Kingscourt Rd) the first to live there was William James, 1736-1822, a farmer who came from Wales. This man William James of Curkish was the great-grandfather of two famous American Citizens.
  
  (i) William James, 1842-1910, Philosopher (ii) Henry James, 1843-1916, Novelist ("The Portrait of a Lady" and "Bostonian's") There is a memorial window to the James Family in the Church of Ireland.
  
  
• Birthplace of Francis Sheehy Skeffington
  
  Across the street is Jameson's Pharmacy, here Francis Sheehy Skeffington was born in 1878. His father was J.B. Skeffington, from Co. Down, a school's inspector and working at that time in the Model School. During his time in Bailieborough, Francis was born. He was a leading socialist, pacifist and supporter of the feminist movement. He married Hanna Sheehy in 1903 and in support of her and his own feminist principles he adopted her name as part of his own. An eminent journalist, he was co-founder of the "Irish Citizen", in support of the Irish women's sufferage movement. He had many famous friends who included James Joyce, James Connolly, WB Yates, The Parkhursts, Constance Markievicz and Sean O'Casey. A pacifist, he did not support the 1916 Easter Rising but endeavoured to prevent looting and assisted a wounded British Officer to safety. He was however arrested by the British forces and murdered by a mentally deranged officer.
  
  
• Bridewell
  
  Walking on down the hill we come to the Courthouse, the oldest building in the town, built in 1817. A "Bridewell", or short term prison, was added in 1833 and used for detention until 1900 with the jailer and his family living upstairs over the detention cells. Cross over the road and look back at the massive wall at the side and rear of the building and you will be in no doubt about its effectiveness as a prison. The initial meeting of the Bailieborough Board of Guardians (Lord Lisgar Chairman 1839-1876), Ireland's first attempt at local democracy, the forerunner of the modern County Council, was held in the courtroom and during difficult famine times meetings were held there for safety reasons. Two notorious murder cases are associated with the Courtroom. (i) "The Ribbon men murder" 1858, the guilty were exiled to Van Demons Land now Tasmania. (ii) "The Nolagh murders" 1898, the accused was hung in Belfast 1899.
  
  
• Wesleyan Chapel
  
  Turn to your right down Adelaide Road, called after Lady Adelaide Lisgar, you come to the Wesleyan Chapel built 1833 and the two story house alongside it, it's Manse, which served the Methodist community.
  
  
  
  
• Ruins of the old Church of Ireland
  
  Adjoining the church ruins is it's accompanying grave yard containing the now marked Famine Graves. Amongst the plots you will find those of the James Family of Curkish, Edward Tuite Dalton, who was Lady Lisgar's first husband she is buried in Co. Meath. His brother, Gustavus Tuite Dalton lived in the Castle and was the first editor of the Anglo Celt, our county's newspaper and Rev. Charles Claudius Beresford who ministered in the Parish during the famine and died of fever contacted from a borrowed coat of one of the famine victims. He was buried on 28th August 1848.
  
  
• Church of Ireland
  
  The Church of Ireland occupies a commanding position at the lower end of the main street. At a vestry meeting held on the 14th May 1833 it was decided to build a Church at the lower end of Main St. The minutes of this meeting were signed by Rev. John Gumley who became the Church's first rector. The church was erected between 1833 and 1835, but it was not consecrated until 1842. In 1864 a transept was added to the north side of the church. While Rev. Thomas Jackson was rector in 1871, a Parochial Hall was built on the grounds. In the Church, can be seen the restored memorial window to Lord and Lady Lisgar, while in the graveyard, their remains are contained in the burial vault of the Young family. Sir John Young was MP for Cavan 1831-1855, Joint Secretary of the Treasury 1841-1844, Chief Secretary for Ireland 1852-1855, Lord High Commissioner of the Ionic Isles 1855-59, Captain General and Governor New South Wales 1860-67. He was appointed first Governor General of Canada in 1868 and was raised to the Peerage as Baron Lisgar of Bailieborough where he died in 1876
  
  
  
  
  
  
• Model School
  
  Turning left into Church Street we see in front of us the Model School, a cut stone building in Tudor Style, built in 1848. Sir John and Lady Young were visiting Lord and Lady Farnham at Cavan. Lady Young and Lady Farnham were discussing the building of a new Model School. Lady Farnham argued that the Model School should be built in Cavan. However, Lady Young, felt that because Cavan already had the Royal School the Model School should be built in Bailieborough. At the time the two ladies were playing cards. They agreed that they would use their game of cards to decide on the location of the Model School. Lady Young won the game so therefore the Model School was built in Bailieborough! Sir John Young donated the site and funded the building of the school. Model Schools were part of a far reaching educational experiment to provide primary education for all denominations, and basis for teacher training. Initially it was a fee paying school, but today it is one of approximately 6 nation-wide Model Schools, which are directly managed and funded by the Minister of the Department of Education. The school continues to educate the Church of Ireland and Presbyterian communities.
  
  
• Site of Bailieborough Workhouse
  
  A short distance further on the shores of the town lake is Fairlawns, a nursing home for the elderly. Earlier this site was occupied by Bailieborough workhouse built in 1841. During the Great Famine as many as twelve hundred poor men, women and children crowded into its shelter and within its walls many of them died buried in the famine mass graves (site 8). The Workhouse closed in the 1920's having previously served as a fever hospital. In 1922 the Free State Army occupied the Workhouse. Following the Free State Army's Occupation it became one of the first Technical Schools in the country. It's use changed again in 1936 when the building became a manufacturing base for shoes and boots produced by the George Earl Company. The "Boot Factory" was the main source of non-agricultural work in the area for nearly 40 years.
  
  
• St. Annes Church
  
  Enjoy the lake-shore walk along the "Town Lake" and through the Town's Nature Preserve, which takes us to the next location of historical interest St. Anne's Catholic Church. It was built in 1834, to replace the old church, a few years after Catholic emancipation. The original church was described as a long thatched building, and was often referred to as the "thatched chapel". The tower and belfry were added in 1861, in 1870 the chancel baptistery and sacristy were added. The stations of the cross were erected in the 1940's, they were painted by the famous Irish artist George Collie and are one of a kind. Until a number of years ago the bodies of the parish priests were buried in the church and memorial plaques are to be seen on the walls of the church. It is also to be noted that the front rows of the left wing was where the wealthier Catholics of Bailieborough were seated during prayer, although no such rule applies now.
  
  
• Tandagree House
  
  Built in the 1840's by Sir John Young, for his agent Thomas Chambers, who administered his estate and collected his rents, while his boss occupied his world-wide Governor General positions. Private families who lived in this house included Isaac Broom, Justice of the Peace and his wife Mary Williamson. They donated the land for the building of Trinity Presbyterian Church, across the road. The house changed possession to Charles Hourican, remembered as a keen greyhound sporting enthusiast. In 1945, the Presentation Sisters, purchased the house with 9 acres of land for the sum of £1,750. They converted the house to a convent from where sisters travelled all over the world including India, Pakistan and California. Sr. Josephine O'Shea established the Secondary Convent School in 1965, which is now the Community School.
  
  
• Presbyterian Church
  
  Across from Tandragee House is the Presbyterian Church dedicated to the Most Holy Trinity and opened for worship in 1887. It replaced the older Second Bailieborough church built 1770 which was a mile further out of town at Urcher, adjacent to the Virginia Road. The hall was added in 1911.
  
  
  
• Model House
  
  Walking onto the Kells Road you arrive at the Town's Health Centre - Teagasc Agricultural offices, which was the second location of the townàs Vocational Technical School and previously the site of the Model House. Built in 1847 the Model House was originally built as an Agricultural Training School by Lord Lisgar. Students were given instruction in the theory and practice of Agriculture. Attached to the Model House was a farm of 48 acres. In addition to the students of agriculture, groups of trainee teachers and masters from the Model School were boarded in the Model House. The Agricultural School closed in 1875 and later when training colleges were established in Dublin, the Model House was no longer used to accommodate training teachers. The farm was taken over by Lord Lisgar while the house was changed to the residence of the Principle Teacher of the Model School. After the Vocation Education Act became law in 1930 a Vocational School was established in a portion of the old workhouse. Three years later this was transferred to the Model House. In 1965 a new Vocational School was built on the same site. We the people of Bailieborough hope you enjoyed your walk around our town. If you are staying for some time you can visit the Castle Demesne, once the home of Lord and Lady Lisgar and enjoy the scenic Castle lake, or visit Corglass Church the home of the first Bailieborough Presbyterian Congregation. Built in 1714, was once the centre of a densely populated area, with houses and taverns. the graveyard contains a number of interesting tombstones. Exploring the Castle Woods you will discover the Dungannon Fort and pause a while at the memorial to those who died during the local 1798 upraising on Rebel Hill. If you still have lots of energy try cycling along peaceful country roads to Skeagh Lake and finish by climbing to the top of our fabled Lough-an-Lae Mountain.