Evidence of settlement in the Cookstown area dates back to around 3200 BC but the real history of the town only began in the Seventeenth Century.

When James the first acceded the English throne in 1603, he faced financial ruin.  Securing his succession had been an expensive business and his profligate lifestyle had led to the accruement of huge debts to his Scots and English subjects.  In an attempt to salve his financial sores whilst at the same time removing the threat of Rebellion among his Irish subjects (especially in Ulster where the old Irish landlords  led by the Earl of Tyrone had rebelled unsuccessfully against Elizabeth I), James decided to demise upon his debtors large tracts of land in the northern parts of Ireland.  These lands had formally been in the possession of Rebellious Irish landlords who had fled the country after the failure of Tyrone's rebellion in 1607.  The demise of land was usually made on condition that the lands be developed and made profitable.  The wholesale plantation of Ulster began in earnest in 1609 when hundreds of English and (much more significantly) Scots "undertakers" were granted leases of land in Ulster .

The lands around the present site of Cookstown had formally been in the hands of the O'Mellan Clan and was broadly known as "Mellanagh".  This land was confiscated by James and held to be the property of the Established (Anglican) Church and was thus presented to the Anglican Archbishop of Armagh who was charged with overseeing the settlement of the area.  In 1620, a small portion was leased by James Stewart (whose successors had a huge impact on the town a century later) and lands around the townland of Cor Criche were leased to an ecclesiastical lawyer, Dr Allen Cooke. Cooke fulfilled his part of the lease by building 10 houses on the land (today covering the area known as Oldtown) which he stipulated were all to have front gardens (a tradition which until recently remained in place).  In 1628, Charles II granted a Patent to Cooke permitting the holding of a weekly market (which still exists to this day).  It was thus that "Cooke's Town" was originally founded.

In 1641, the native Irish revolted against the Planters in a bloody rebellion.  Cookstown, being in the heartland of Ulster insurgency, was abandoned to the rebels who immediately seized the important Iron works at Lis Aine (later Lissan) and the area became a hotbed of activity as pikes and weapons were forged for the rebel cause.  Lissan was one of the first estates in this area to be settled when it was demised to Thomas Staples of Yate Court near Bristol in 1610. His son Robert Staples constructed a great house on the estate around twenty years later and this structure (though disastrously extended ever since) still survives today.  Lissan House lies on the outskirts of Cookstown.  It is a huge structure of little architectural beauty but enormous historical significance and was, until the death of its last inhabitant, Hazel Radclyffe Dolling (daughter of the 13th Baronet of Lissan, Sir Robert George Alexander Staples), in 2006, the oldest domestic dwelling in Ireland continually inhabited by one family.  From outside it rather resembles a large industrial building and was not helped by the insertion of steel framed plate glass windows in the early twentieth century.  The entrance front is dominated by a gargantuan porte cochere built in about 1830 complete with coachman’s rooms.  Inside, one is immediately stuck with the appearance of the bizarre and gargantuan oak staircase which rises from the stone flagged entrance hall the full height of the building.  This was constructed by a local carpenter from the remnants of a rare seventeenth century staircase which collapsed (along with the floors between it) as a result of dry rot in the 1880’s and is quite unique, having flights springing at every conceivable angle (some of which go nowhere) and going to every conceivable nook of the house.  The other most notable feature of the house is its grandly dignified octagonal ball room added by Sir Thomas Staples (Queen’s Advocate in Ireland ) in about 1830 with its fine if rather restrained neo-classical plasterwork, Dublin chimneypiece and carved door frames.  The house currently lies empty, its contents in storage, but a Trust was established on the death of Mrs Radclyffe Dolling to oversee the restoration of the house and its development into accommodation and conference facilities.

The first settlers of the Lissan Estate did not escape unharmed during the 1641 rebeillion.  Sir Thomas' wife  and their five children were captured and imprisoned at Moneymore Castle about 5 miles away and held there until Moneymore and the estate were liberated by Sir Thomas (who had been in Dublin when the Rebellion broke out) and the Royalist army in 1643.  When the armies of Charles the first reached Cookstown in 1643, they ruthlessly routed the rebels and razed the remains of the town to the ground.

It seemed as though the development of a town in the area had been put to a very sudden and final halt.  Over the proceeding years, the lands around Cookstown were progressively bought up by William Stewart, grandson of James, until in 1671 all of Dr Cooke's lands were in the hands of the Stewarts and they had created the Castle and Demesne of Killymoon.  Settlement however remained sparse to say the least and by 1734, only 2 inhabited houses remained at Oldtown.  William Stewart and later his son James set out daring plans for the town soon after this.  Inspired by the Wide Street Commission's work in Dublin, they planned a new town to be built along a tree lined boulevard 135 feet wide which would connect the Killymoon Demesne with Oldtown, a distance of over a mile and a quarter.  This elegant street was laid out by the mid 1740's and has remained at the centre of Cookstown's development ever since covering Killymoon Street, Church Street, Chapel Street, Loy Street, William Street, James Street and finally Oldtown Street and being the longest main street in Ireland.  All traces of Cooke's town were obliterated at this point.

Throughout the remainder of the eighteenth century, Cookstown prospered quietly as a market town where linens, seeds and other agricultural produce were marketed at its famous market.  In 1802, Col William Stewart  (James Stewart's unmarried son) approached the famous London architect ,John Nash and requested that he visit the area to rebuild the Castle of Killymoon which had been burnt in 1801.  This imposing structure is Cookstown's finest piece of architectural heritage.  It was built in just over a year at a cost of £80,000 and was Nash's first Irish Commission.  It is two stories high and has two large towers to the East and West, one circular the other (slightly lower) octagonal.  Parts of the original castle were retained and its former Chapel became Nash's library.  Inside the dramatic entrance porte cocherecan be found a stunning return staircase leading to the octagonal drawing room and oval dining room.  The Stewarts sold the castle in 1852 and, after passing though the hands of some 6 owners, it was sold for the final time in 1922 to a local farmer for the princely sum of £100.  The same family retains it to this day.

In addition to Killymoon, there is evidence to suggest that Nash also designed the original St Luran's Parish Church on Church Street in 1822 and certainly plans for the church exist in his hand.  However, even if Nash's church was completed, at most only the tower and first bay of this structure have survived Victorian extension by the rather dull architect Welland in 1859.  Nash's plans show a castellated and battlemented church from which only the tower and spire bear any resemblance to the structure standing today.  The interior is an entirely uninspiring and typical Victorian church structure with a chancel arch, hammer beam roof and large sanctuary with sparse but dignified decoration.

It is also suggested that Nash designed the Dower house of Killymoon on Chapel Street (now divided into two houses) and it is certain that he designed the Rectory at Lissan (a wonderfully frilly exercise in toy Gothick) for the Rev John Molesworth Staples in 1807.

However, as with most provincial towns in Ireland , Cookstown's greatest development came with the industrial revolution.  With the establishment of Gunning's Linen Weaving Mill, the expansion of the Wellbrook linen finishing estate, the establishment of Adair's weaving mill at Greenvale and the final arrival of the railways, Cookstown's population quadrupled between 1820 and 1840.  The railways allowed the fast transport to and from the town of agricultural produce and the town's expansion seemed unstoppable.  Two railways established termini at Cookstown - the London, Midland and Scottish Railway in their dignified dressed stone station designed by Charles Lanyon (now much altered as a Chinese restaurant on Molesworth Street) and the Great Northern in their pretty picture book brick station next door (now Cookstown High School's Hockey Club).  Both transported goods and livestock for sale to Cookstown's market which flourished as never before.

With the exception of Killymoon Castle, all of Cookstown's best architecture dates from this period and the town still resembles almost exactly the town developed at this time.  Probably foremost among the buildings of this period is JJ McCarthy's Church of the Holy Trinity on Chapel Street.  This magisterial structure was constructed between 1855 and 1860 with a soaring tower and spire at the West End .  It is one of McCarthy's earliest works in which the influence of Pugin is still paramount and the later florid French Gothic of his latter years is nowhere to be seen.  The church is constructed in the Early English style with a nave of 5 bays leading to a chancel arch and reduced chancel area beyond.  Until the early 1980's this area was a riot of stenciled decoration, stained glass, mosaic, carved marble and Caen stone, but at in 1980 the side altars, marble altar rails, spectacularly carved pulpit, original high altar and Telford Pipe Organ were all ruthlessly torn out and dumped outside the baptistery which was itself cleared of its font and shuttered off.  The remaining neo-Gothic stenciling work was painted over and the ceiling stenciled work painted over in a ghastly shade of pale blue whilst the marble and mosaic floors to the Chancel were carpeted over. Only the gargantuan Caen Stone reredos survives (minus its central spire and High Altar) in a somewhat tatty condition behind one of the reclaimed Caen stone and Carrera Marble altars, the front of which bears a carved representation of the Assumption of the Virgin (presumably formerly in the Lady Chapel which would have been to the right of this space).  The crowning feature of the church today is the magnificent and utterly titanic Eastern Window.  This was designed and manufactured by Hardman of Birmingham (a firm employed and partly run by AWN Pugin) and has representations of the Canonized Bishops and Abbots of the Archdiocese  around a representation of the Virgin crowned in glory and below a tripartite window representing the constituents of the Holy Trinity.  The remaining stained glass is mainly by Mayer of Munich and dates to the end of the nineteenth century (representations can be found of the Holy Family, the revelation of the Sacred Heart, Sts Brigid and Patrick) though there is a very fine Art Deco window showing the Annunciation in the style of Harry Clarke in the former Lady Chapel (now a seating area).  Much of this glass has very recently been damaged and it is particularly distressing to see one of the lower panels of the spectacular Hardman window (unique in Ireland ) with a large hole present.

Other fine buildings of this period include the muscular Scots-Baronial former Courthouse (currently derelict) on Chapel Street ; the dignified Classical First Presbyterian Church (Loy Hill) and Romanesque Molesworth Presbyterian Church ( Molesworth Street ); the pretty provincial Romanesque Methodist Church ( Church Street ); the Provencial Bank of Ireland on James Street (destroyed ny terrorist activity) and the pair of railway termini aforementioned on Molesworth Street .

It was around this time also that Viscount Stuart (later the Fifth Earl of Castlestuart) married Augusta Richardson-Brady, heiress to the Oaklands estate on the outskirts of town.  Immediately upon the marriage, Lord Stuart set about reconstructing Oaklands into the splendidly camp Tudor revival Drum Manor.  This fine battlemented sandstone structure once had a tall tower to the East near the entrance front which was dominated by a gargantuan entrance portal surmounted by a large tracery window which contained some splendid Victorian armorial stained glass.  Lord Stuart was also responsible for setting out the formal gardens and Demesne which survive to this day (in varying states on disarray).  Drum was, until 1980, the finest example of its type in the Cookstown District.  In that year, Lord Stuart’s grandson sold the estate to the Forestry Commission who set out the fine woodland habitat that exists there today.  However, in an attempt to avoid incurring Rates liability, the Commission tragically decided to demolish the Manor.  Today, Drum Manor Forest Park is one of Cookstown District’s largest tourist attractions (complete with the highest-rated caravan site in the District) but the Manor lies forlorn, only its ground floor and tower surviving.  Inside, where once there was a vivid collection of gothic carved wood, mosaic and stained glass, today exists a ghastly overgrown and totally incongruous faux-Japanese garden.  Only the Manor’s two pretty gate lodges remain intact to hint at the former grandeur of the estate.

With the linen and later the hat-making and brick manufacturing industries, Cookstown continued to prosper in the early twentieth century and its population continued to expand.  Little architecture of any note dates from this period as the grandiose Victorian structures of the previous generation continued to fulfill their purpose admirably.  The Great War had a devastating effect on the local community at a cost of life commemorated in the prominent Cenotaph (loosely based on Lutyen’s Whitehall Cenotaph) at the centre of the town.  This is Cookstown’s sole piece of public sculpture.  As industry developed, a Technical College was established on Loy Hill in an imposing Queen Anne style red brick structure.  This was opened by Mrs Adair, whose husband owned the Greenvale Mill, in 1936 and the building currently lies derelict awaiting development.  All of Cookstown’s main educational institutions date from this period, Cookstown High School seizing the Victorian mansion and former residence of the Gunning family at Coolnafranky and the Catholic Church constructing its Convent Schools and St Mary’s Boy’s School (now demolished) all on Loy Hill.

With the outbreak of the Second World War, Cookstown became the centre of much regimental activity.  Killymoon was requisitioned by the American Army and a large internment camp was established on the recently reclaimed land at Burn Road .  The town suffered no enemy damage during the war and the industries of the town prospered as never before.

This however proved to be the last belle époque of the industrial town of Cookstown .  Whilst to some degree the linen industry survived in Ulster until well into the 1960’s, increased fabric imports from the Far East rang the death knell for the industry across Northern Ireland .  Cookstown attempted to put on a brave face, constructing its distinctively moderne town hall in 1953 (now demolished) and opening the Daintyfit clothes factory on Burn Road as well as establishing an internationally renowned Agricultural College at Loughry, but the prosperity of the town was now severely in doubt.  Gunning's mill closed in 1956 and was swiftly followed by Adair’s Mill and the Wellbrook estate.  The railways ceased to operate from the town in 1963 and whilst the market continued to be held on Saturday, its agricultural significance to the wider Ulster community never recovered and the sale of livestock finally completely ceased in 2004.  One ray of light for employment came in 1970 with the opening of the Blue Circle Cement factory at Derryloran. This provided much in the way of employment for the local population, but the factory has polluted the town ever since.  The sole building of architectural note from this period was Liam McCormack’s somewhat incongruous Chapel, the cube-shaped body of which is tacked on to the high Victorian Gothic Convent of Mercy at Chapel Street at one of its corners.  This most unusual patterned concrete and bronze façade was constructed in 1965 and contains (now greatly damaged) important stained glass by the Dublin artist Patrick Pye. Like the convent to which it is attached, the Chapel has suffered greatly by falling vocations and it currently lies derelict.

The darkest period for the town was undoubtedly the period now known as the “troubles” – 1969-1996.  Cookstown always had a vibrant community composed of almost equal numbers from both sides of the sectarian divide but this once creditable state of affairs proved to be a thorn in the side of the town during this period when one faction rallied against the other.  Cookstown became one of the most bombed provincial towns in Northern Ireland , robbing the town centre of most of its finest buildings including the wonderful carved sandstone façade of the Hibernian Bank as well as the Adair’s former high Italianate residence at Glenavon (which had been converted to a hotel).  As atrocity followed atrocity, the town foundered – at one point it was decided not to rebuild the town’s main post office as it had been destroyed so often. The scale of terrorist activity escalated to such a point in the town that in 1989 it was decided that two permanent armed checkpoints should be erected at either side of the town centre and a huge army base was established at Church Street.  Barriers were also erected around the town so that the Main Street could be cordoned off in the evening.  The town was devastated by this activity.  Virtually all industry abandoned the town, its nightlife died overnight and tourism was non-existent.

All of this came to an end with the terrorist ceasefire of 1996.  Following this event, the town slowly began to regain its civic confidence.  In 1999 the town began a plan to regenerate the devastated town centre which had been blighted by the destruction of its Victorian buildings and the construction of their substandard and utterly charmless replacements.  The tree-lined boulevard dreamt up by James and William Stewart was restored and a scheme of regeneration saw the creation of green space, flowerbeds and restored shop frontage.  With Ulster's industry now substantially defunct, the town began to attract instead financial investment from shopping and tourism.  In 2000, the architecturally uninspiring Burnavon Arts and Cultural Centre opened on the site of the former Town Hall on the Burn Road and began to attract large scale cultural and artistic events to the town whilst a year later, a development scheme began which saw the former LMS Railway Terminus turned into a shopping centre.  Today, Cookstown has been almost completely regenerated with plans for further regeneration work to be carried out throughout the town centre. Another large shopping centre on Molesworth Street was built in 2007, and is now being extensively extended.  The old Gunning and Moore Weaving Mill at Broadfields has been transformed into a large retail park with outlets of Tesco, Marks and Spencer, Homebase and Next being the first of a planned many to set up here.  The formally untapped tourist potential of Cookstown  is now in full flight with local sites of historic interest (including the last surviving Linen Beetling Mill at Wellbrook, Drum Manor Forest Park and soon Lissan House) attracting many hundreds of visitors per year.  The town’s central location and many hotels (for a population of just over 11,000 it has no less than 4) has meant that it is a natural location for conferences and meetings involving delegates from across Northern Ireland.  It was the natural choice of location for the Mid-Ulster Sports Academy (established in 2003) and the planned Police Service of Northern Ireland training academy (which is to be built at Loughry commencing in early 2009).  The District Council has, in recent years been determined to establish Cookstown as the so-called "Retail Capital" of Mid-Ulster and has begun a concerted re-branding and marketing of the town nationally.  The Council, which recently appointed a Town Manager as an experiment in town planning, has secured many millions of pounds in funding and has ensured that inward investment has been at its highest level since the establishment of the town in the seventeenth century, developing beyond recognition the tourism, retail and hospitality sectors in the area.  With these developments, the future of the town seems secured once again and it is to be hoped that the true value of the town may once again be appreciated by its inhabitants and visitors alike.