In the fifteenth Century the O'Dowds (O'Dubhda) ruled tireragh. And various branches of the O'Dowds took over different parts of Tireragh as landlords. Around this period several castles were built in Tireragh, including Enniscrone.

Albanach Mor built the origional castle in Enniscrone.

In 1512, During a war between The Macwilliam Burkes of Mayo and the O'Donnells of Donegal, Enniscrone castle was captured by burke. O'Donnells besieged the castle with his army for four days until it was surrendered. He took the garrison as prisoner and demolished the castle. The O'Dowds suported the O'Connors of sligo against O'Donnel and soon rebuilt the Enniscrone castle in order to Protect the local area.

In 1597, Enniscrone Castle had been sold to John Croft by Fearadach and Cormac O'Dowd, and it is then thought to have been sold to Thomas Nolan of Ballinrobe and it stayed in this family until The rebellion of 1641/1642. At ten o'clock on a winters night in january 1642 a party of armen men attacked he castle

There is a plaque dated around 1783 and is now set in the north wall of the church, erected in Valentines memory by the then Bishop Perry of Killala. It is still there today and bears th following inscription:

"Here lyeth the body of the Reverend Thomas Valentine formerly the vicar of this union who died on the 8th day of November 1765 in the 90th year of his age. He resided 53 years in this parish and having spent that time in exemplary piety and continued acts of good nature and charity he bequeathed at his death six hundred pounds for the support of the distressed widows of the clergy of the diocese, and four hundred pounds for supporting a charity school and for apprenticing poor children. William Cecil lord bishop of Killala and Achorny has caused this stone to be laid to perpetuate the memory of this worthy man and to propose to every future incumbent a perfect model of a Parish Minister"

Valentines church was ransacked around the time of the 1798 rebellions. It is unlikely that the building was repaired since. It is also likely that the plaque now set into the north wall was origionally the tombstone of Rev. Valentine and was set up in its present position after the church had been ransacked

In 1883, the Rathlee;en route from Ballina to Liverpool with general cargo, was wrecked on Enniscrone beach. She left ballina with only half her crew of ten, the remainder being in Ballina, buying provisions, and not having reached the Quay when the turn of the tide forced captain Edgar to take out his ship, and the fiveremaining crew were to join the ship in Enniscrone.

The ship crossed the Bar safely, Phelim O'Neill landed the pilot at the Boat port as the present pier had not been built at this stage. While the ship lay on anchor, a ground sea came in and she dragged her anchor.The remainder of the crew arrived from ballina on a side car driven by a man named Callaghan. By the time they reached te boat port the ship had grounded and was being battered on the shore by the wind and waves. Many attempts were made to refloat the Rathlee but she became a total wreck.

She lay as is seen in the photograph until she was partly broken up and sold to buisnessman Arthur Muffeny for scrap. the remains of the Rathlee have recently been uncovered by winter storms for the first time in over a decade.