Unlike most towns in Ireland, which emerged and grew about a focal point such as a Church, Enfield's phased growth is paralleled with the various phases of transport history. Enfield has a long association with the hospitality trade as a stopover for the weary traveller.

Going back to Ancient Times, prior to and during the early part of the first millenium A.D., the Enfield area was situated on the route of the Slige Mór, the great East-West Highway between Dublin and Galway and one of the main roads to Tara, the coronation site and ceremonial seat of the High Kings of Ireland from the time of the early Celts until 1022 AD (shortly after the death of the last unopposed High King of Ireland Brian Boru who ended 200 years of Viking terrorisation at the Battle of Clontarf in 1014). Mael Sechnaill II of the Kingdom of Meath was restored to the High Kingship but he died in 1022. From then until the Norman Invasions, the Kingdoms of Ireland were politically divided.

The Annals of the Four Masters and other Sacred Texts claims that from Tara, the great heart and centre of the Irish Kingdom, five great roads radiated to the various parts of the country:- The Slige Cualann (which ran south-east through Dublin and on to Bray), the Slige Mór (the great Western road ran south west from Tara and went via Trim towards the Clonard/Enfield area to join the great Connaught Road connecting Dublin with Galway which followed the path of the Esker Riada), the Slige Asail (which ran due West towards Lough Owel near Mullingar and then probably in a north-westerly direction), the Slige Dala (beginning in Kells, passing through Tara and heading south east towards Carrick-on-Suir, and the Slige Midluachra (the Northern road running in the direction of Slane and on to Antrim). 

In 1166, Diarmaid Mac Murchadha (Dermot Mac Murrough), considered to be the most notorious traitor in Irish history, was ousted as King of Leinster by the High King of Ireland Ruaidrí Ua Conchobair for the abduction of Dearbhforghaill (Dervorgilla), the wife of one of his allied Kings, the King of Breifne, Tigernán Ua Ruairc. Mac Murchadha asked King Henry II of England to help him recover his throne, and found help from the Welsh Baron Richard de Clare (Strongbow). Mac Murchadha promised Strongbow his daughter Aoife in marriage and succession rights to his Kingdom if he helped to recover the throne. The subsequent invasion by Strongbow and by Henry himself in 1172 marked the beginning of 800 years of English rule. Diarmaid Mac Murchadha may be buried in Clonard, 8 miles west of Enfield, though a cross said to mark his burial place stands in the grounds of the Cathedral in Ferns where he held his seat.

After the Norman Invasions(1169-1172), and the repulsion of Ruaidrí Ua Conchobair from the Kingdom of Leinster, and following the Death of Diarmaid Mac Murchadha himself in 1171, Strongbow claimed Mac Murchadha's Kingdom of Leinster on behalf of his wife.
King Henry II however only permitted him to retain County Kildare. The construction of nearby Trim Castle, the largest Anglo-Norman castle in Ireland, was begun by Hugh de Lacy around 1173, and is a major construction of the Norman period and was part of King Henry II's plan to curb the expansionist policies of Strongbow. Strongbow granted the manor of Maynooth to Maurice Fitzgerald (around 1176) who built Maynooth Castle. Over the centuries, the Fitzgeralds consolidated their power and riches and in 1316, King Edward II made John Fitzgerald the first Earl of Kildare. The 19th Earl, Robert Fitzgerald, began a new seat at Carton House in 1739, the Georgian Mansion was remodelled and in 1744 he was succeeded by his son James who became Duke of Leinster in 1766. The ancient name of Maynooth "Magh Nuadhat" means the plain of Nuadhat. Nuadhat is referred to as the maternal grandfather of the legendary Fionn Mac Cumhaill in the "Annals of the Four Masters".

As the Fitzgeralds stengthened their stronghold of the area, a road was built during these times from Maynooth Castle to Courtown House in Kilcock (once the residence of Film Director John Houston), to the Windmill on Cappagh Hill, to Cloncurry over to Johnstown House (now the Johnstown House Hotel and Spa), and from there on to Newcastle and Balyna House (now part of the Moyvalley Hotel and Golf Resort).

When the Stage Coach was used as a form of transport in Ireland, this road took a slightly different route to include the area that is now known as Enfield. The road from Dublin running through Enfield to Mullingar was built around 1735. During these times the area was known as New Inn or Innfield, referring to the original Royal Oak Inn in the area. In those times, due to the conditions of the road, coaches could only travel 30 or 40 miles in a day and travellers needed somewhere to eat and rest. Later, the Inn had associations with Bianconi's horse-drawn carriage network which operated from around 1815 into the 1850s providing public transportation in Ireland at a time preceding railways.

A livery stable and courtyard existed opposite the old postoffice building (now a Chinese Restaurant) at the East end of the town, to service people travelling on this road. Fresh teams of horses were available for hire at the livery stable when the coaches stopped at the postoffice. The building also provided some stopover accomodation. Some of the remains of the original livery courtyard can be seen today adjacent to the Centra supermarket and car park. These sites were protected once by the Office of Public Works but unfortunately have made way for redevelopment. The first postal deliveries by stage coach, in the area, occurred around 1740, during the time of Robert Fitzgerald, 19th Earl of Kildare.

The original Inn is believed to have been on the site of The Bridge House bar and restaurant. This building had a thatched roof until the 1940s. The stage coaches were responsible for the Irish name of the area, known as 'An Bothar Buí' which means the yellow road. This name was derived from the yellow mud that formed on the road through a combination of rain and the churning effect of the wheels on the soil. Another theory is that the name arose from the yellow colour of the ragworth vegetation at the sides of the road.

The name Innfield became Enfield towards the end of the 19th Century when a new postmaster came from the Enfield district in London and decided to use the same name for the area. Innfield still appears on many maps as the official name of the area.

The Royal Canal construction began in Dublin in 1790 and this signaled the end of the stage coach era, as the canals were a cheaper and more efficient means of transport. The stretch from Dublin to Mullingar opened as a trade route around 1807 and the canal eventually reached the Shannon in 1817, though the company was heavily in debt. The decision by the Duke of Leinster to build a spur from the canal to his country residence, at Carton House, was one of the contributing factors which finally broke the company.

The canal was sold for £300,000 to the Midland Great Railway Company. The Railway bought it as a strategic move to subsume the transportation business of the canal and planned to drain it and lay tracks over its route. Thankfully, this didn't occur, partly because the line of the canal had too many unsuitable bends.

Unlike the Grand Canal, the Royal Canal was never profitable and was replaced by Rail Travel in 1847, only 57 years after the project to build it began.

The Mullingar line was opened for public traffic as far as Enfield on July 2nd 1847. The first and second class carriages were divided into passenger compartments, some with beds, and designed to a high degree of quality and style. Some carriages were for the exclusive use of women.

Even though rail travel was much quicker, the canal continued to carry traffic until the 1950s. Both the canal and the railway had stop over points in Enfield, and this contributed to the development of the area.

It is only now, at the turn of the millenium, that the potential of the Canal for tourism and as a natural amenity is being realised. The Office of Public Works took charge of it in 1986 and subsequent investment and significant restoration means it has great prospects of becoming  popular again as a means of leisurely transport.

The harbour area at Enfield has been completely restored and transformed into a beautiful leisure park.

Barringtons Hotel, on the site which is now Flatterys Pub and Restaurant since 1959, grew up as a result of the railway. A number of other public houses and hostelries emerged in the area because of the influx of population.

The Midland bar has been on its present site since the late 1800s. The site where the Slíghe Mór pub stands used to have a hardware shop, bicycle shop and grocery at the turn of the 20th Century. In the 1940s, the Maugherbawn restaurant (Macaire Bán means White Plain, possibly referring to the white hawthorn of the surrounding flat area) opened there and the building progressively changed and developed into a hotel. Part of the building has now been converted to a betting office.

The first Motor Cars were used in the area around the turn of the 20th century. During the 1940s, the Harris family had the dealership for Morris cars and Claas combine harvesters and operated a garage to the rear of Ryans's Newsagents, where Riki's garage continues to operate today.

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