Holywood enjoys an enviable reputation as a vibrant, speciality shopping town, located on the southern shores of Belfast Lough. The commercial core of Holywood is High Street with the town’s maypole (the only surviving one in Ireland) intersecting it with Church and Shore Road. Holywood enjoy's impressive views across the Lough to the Antrim Hills.
The earliest documented reference to Holywood was made in the 7th century regarding the monastery of St Laiseran, founded on the site of the present ruins of the Old Priory. The Norman knight John de Corcy invaded the east coast of Ireland in the late 1100s and after defeating the local clans built many fortifications called Mottes and Bailies along the Antrim and Down coasts. It’s rumoured that De Corcy spent a night at “Sanctus Boscus” Latin for "holy wood” the name the Normans gave the woodland surrounding the monastery. The earliest anglicised form appears as Haliwode in a 14th century document. Today, the name is pronounced the same as Hollywood. The Irish name for Holywood is Ard Mhic Nasca meaning "high ground of Mac Nasca."
In nearby Brook Street is Holywood’s Motte – (French for “mound”). Originally the Motte would have had a wooden defensive fortification at its top and a bank and ditch around its base. In the 12th century, the waters of Belfast Lough would have been much closer to the Motte. De Corcy’s 25 year “reign” in Ireland ended in 1205. De Courcy's lands were awarded to his victor in battle Hugh de Lacy and the title Earl of Ulster by King John.
During the 17th Century Plantation of Ulster, two wealthy Scotsmen Sir James Hamilton and Sir Hugh Montgomery rebuilt Holywood as a market town. Holywood’s Maypole is documented in a Ravens Map of the area dated 1625.
When the railway arrived in 1845 Holywood grew rapidly as a seaside resort. During this period parts of the huge Hamilton estate were sold to settle family debts. As a result, much of the land around Holywood, including the Holywood Hills, Cultra and Craigavad were bought by Belfast industrialists and merchants who built large Victorian mansions as expressions of their new found wealth. In recognition of its unique Victorian architectural heritage the area known as 'High Holywood' has been designated a Conservation Area.