[11] The earliest reference to the actual settlement of Tobermore is in the mid-18th century of a house built in 1727 that belonged to a James Moore.

At some point in the 18th century, the fair that was held at the Gort of the parish church was relocated to Tobermore, which is described as consisting of only Moore's house and a few mud huts.

[14] The rath was historically known under variations of Donnagrenan, which is most likely derived from the Irish Dún na Grianán, meaning "fort of the eminent place".

[15] Fortwilliam rath is presently described as a well-preserved semi-defensive high status monument, built to withstand passing raids, being relatively large at 30 meters in diameter.

[19] In November 1780, a meeting was convened of the Tobermore Volunteer company, commanded by John Stevenson, at which the Reverend James Whiteside preached.

It is stated that the inhabitants resisted the "pounding of their cattle, executed by him, with pitchforks and sundry other primitive implements of warfare".

When they found that resistance was useless they employed Mr. Costello, one of the orators of the Corn Exchange to litigate their cause at the Magherafelt sessions, but here they were also unsuccessful.

[24] A chancery lawsuit going on between Ball and Co. of Dublin and Sir George Hill operated as an obstruction to the improvement of the village as it stood upon the estate disputed with non-payment of rents.

During the same period, it is noted that there was no illicit distillation of alcohol and no outrages for many years in the village except for a few assaults in the street on those who came to collect the rent.

[33] The names of those who volunteered are preserved on a Roll of Honour painted by local man, Samuel Nelson, and was unveiled by Denis Henry, MP for South Londonderry.

[32] In Tobermore's Presbyterian graveyard lies the headstone of Bobbie Wisner, who died of natural causes at home in 1915.

As he had trained and drilled with his adult comrades in the 36th Ulster Division, and was held in such high esteem, he was buried with full military honours.

[36] In response, the Orange Hall on Main Street effectively became a barracks used by members of the Ulster Special Constabulary (USC).

[37] No casualties were reported after police returned fire and the IRA men withdrew, though it was later felt necessary to fit steel shutters to the windows.

The Constitution newspaper states: "It was the first venture of its kind held in South Derry, and it was also among the first organised 'Victory Day' celebrations to take place in the Province.

Not only that, but Tobermore's 'Victory Salute' to that great achievement which crowned the Allied arms so magnificently little over a year ago, was availed of to give practical expression to the pride which the people of South Derry generally take..."[32] The Constitution also states: "In the preparatory arrangements nothing was left undone to ensure that it would prove a resounding success and certainly Tobermore's Victory Fete will long be regarded as one of the most memorable ventures in the district.

"[32] The Victory Fete was attended by Sir Ronald Ross, MP for the City and County of Londonderry, the band of the 1st Battalion Royal Ulster Rifles and the local units of the Maghera and Tobermore Army Cadet Force.

[40] In October 1972, an Ulster Vanguard political rally was held in Tobermore, where Ulster Unionist Party deputy leader, John Taylor, made a speech on the use of violence stating: "We should make it clear that force means death and fighting, and whoever gets in our way, whether republicans or those sent by the British government, there would be killings".

[41] There were four bomb hoaxes in Tobermore during 2010 the most recent on 29 July 2010 and 19 August 2010, both found in the centre of the village causing a lot of traffic disruption and resulting in people being evacuated from their homes.

[42][43] On 29 July 2006, Ronald Mackie, who was visiting from Scotland to attend a loyalist band parade in nearby Maghera, was kicked and beaten before being run over and killed after a row flared during a disco held at Tobermore United Football Club.

Four men were charged and two; John Richard Stewart, from Maghera, and Paul Johnston, from Castledawson, were later convicted of manslaughter.

[44][45] On 16 August 2008, over twelve hours of torrential rain caused the Moyola River to burst its banks and saw the flooding of the main Tobermore-Maghera road, the neighbouring football club buildings and pitch of Tobermore United F.C.

The traditional activities of the Eleventh Night include the playing of Lambeg drums, the parading of the town by the local blood and thunder band and the lighting of a bonfire.

[citation needed] Before the establishment of national primary schools, education lay mainly in the hands of the church.

In Tobermore the Church of Ireland parish of Kilcronaghan has records of its school masters going as far back as Mr. Alex Trotter in 1686.

It received an income from the London Hibernian Society as well as books published by them such as Thompson and Gough's Arithmetic and Murray's English Grammar.

[62][63] For secondary education, students from the Tobermore electoral ward mainly attend schools in Magherafelt and to a lesser degree Draperstown.