King John is supposed to have stayed in this castle for three days in 1210. It was probably built a few years earlier by Hugh de Lacy.
The earliest part is the D-shaped curtain wall in the W. This had a rectangular gatehouse and a square SW flanking tower. Portions of the N tower of the gatehouse still remain. The curtain wall is well provided with deep embrasures with narrow defensive slits. During the second half of the 13th century a large rectangular hall was added on the E side. This is three storeys high including the basement.
The castle stands on a rocky outcrop overlooking the harbour. During the 19th century the Dundalk, Newry & Greenore Railway constructed a deep cutting on the landward side thereby enhancing the prominent position of the castle.
Close to the former railway station is Taaffe's Castle (J189117) which was built in the early 16th century. It is a rectangular tower-house, four storeys high plus the roof walk. It has a projecting turret at the SW corner. The original entrance was in the W wall beside the turret. It was protected by a small machicolation.
To the left of the entrance a short passage led to a spiral stairway in the NW corner. This led to the second floor and was protected by a murder-hole. Another spiral stairway in the SW corner led from the second floor to the roof. There are garderobes at three levels in the NE corner. The tower is vaulted above the first floor. Later in the 16th century a two-storey rectangular addition was built against the N wall.
Just round the corner from Taaffe's Castle is a small three-storey tower-house which is said to be the site of a mint established in 1467 (J189116).
The doorway is in the NE wall near the E corner. It has been partly reconstructed with some finely decorated stones. It is protected by a large machicolation at roof level. There are also fine crenellations. The absence of any fireplace suggests that the castle may not have been used as a dwelling and the strength of the defences reinforces the idea that it may have been a mint. There are some fine windows in the NE wall with hood moulds and mullions. They are richly decorated with pre-Norman motifs such as interlacing and animal and human heads.
A short distance SE of the Mint is the Tholsel (J189118). This is one of the medieval gatehouses of the town. At present it is a two-storey building with a flattened barrel-vaulted archway occupying most of the lower storey. Also at this level is a small windowless chamber which may be entered through a doorway beneath the external stairway near the N corner. This chamber was used in later years as the town jail. The stairway is modern and there is evidence that the original structure was spiral. The upper level of the building has a single rectangular room which was used in later years as a meeting place for the town elders, thereby giving the building its present name. It is lit by five windows and there is a garderobe near the E corner. There is considerable evidence of re-building at this level, including the insertion of the lintel from a small round-headed window.
Near the southern edge of the town stands the ruin of the Dominican Priory of St Malachy (J190114). It is thought to have been founded by Richard de Burgh, Earl of Ulster, in 1305. However it may have been founded by Walter or Roland Joyce, two Dominicans, who succeeded each other as Archbishop of Armagh between 1307 and 1322. In 1423 the church was repaired after damage by enemies and robbers. This may have been when the walls were fortified. After the suppression the priory was leased in July 1541 by Martin Scryne of Carlingford, and it was granted in April 1552 to Nicholas Bagnall.
The remains consist of a nave and chancel church divided by a tower with some fragments of the domestic range to the south. There is evidence of a large E window but all remains of tracery are removed and there is no evidence of the original number of lights. The nave was altered in later times when crenellations were added to the W wall and small turrets were placed at the NW and SW corners. There is a machicolation guarding the W doorway. The tower is a tall rectangular structure which seems to have been added about the middle of the 14th century. There are traces of a stairwell at the SE corner.
The ruined corn mill, a short distance SE of the priory, may be the successor to the priory mill which is listed in 1540.
We visited the church of St James, Cooley which is situated just north of the main road from Greenore to Dundalk. It was formerly the possession of the Cistercian abbey of Newry. It was part of the "Irish Quarter" of the English lordship in the 15th century. It was confiscated after the Suppression of the Monasteries and granted it to the Meryman family until the Cromwellian confiscations of the 17th century. It was probably a church site from the earlier period and the present Roman Catholic church built in 1762 continues this tradition. It is now the oldest of its kind in County Louth and is a beautiful church of simple "penal days" design recently refurbished. The church was originally a "long wall" building with the altar in the middle of the S wall. A northern extension, with a gallery, was added in 1815. The S tower and the galleries in the E and W may also have been added at this time. During the recent renovations two stained glass windows, which had been inserted to flank the altar in the 1920s, were removed and the original window openings restored. These windows are probably from the Harry Clarke Studios but they are not signed. They were designed as background to two statues and have now been re-erected inside the church and are backlit by artificial light.
All the windows now have typical Georgian glazing bars with some Y-tracery and attractive fanlights over the doorways.
At Rockmarshall (J124080) there is the low ruin of a court-tomb. It may be reached by a lane running E from the R174 close to the junction with the R173. A four-chambered gallery leads SW from a semi-circular court. A field wall encroaches on the tomb and the SE arm of the court is missing. The NE arm is represented by six stones and the court would have been about 3.5m deep. The entrance to the gallery has a double jamb but only one of the inner jamb stones survives. The first chamber is 2.9m long by 2.4m wide with one stone forming the NW wall and two stones in the SE wall. A pair of jambs leads to the second chamber which is slightly smaller than the first, with two stones in the NW wall but only one remaining stone in the SE. A pair of jambs leads to the next chamber, but here there is a gap, less than 1m long, before the chamber is reached, beyond a single surviving jamb stone. This chamber is about 4m long and narrower than the first two chambers. The NW wall has four stones but only one stone survives in the SE wall. A single jamb stone leads to the fourth chamber which is about 2m long and very fragmentary. It is only about 1.4m wide. The gap between the second and third chambers cannot be easily explained.
The megalithic tombs at Proleek are situated beside the golf course adjacent to the Ballymacscanlan Hotel and may be reached via the cark park or from a minor road a short distance to the east.
The portal tomb (J082110) consists of a chamber facing NW and composed of a massive capstone resting on two portal stones and a side stone. The capstone measures 3.8m by 3.2m and is estimated to weigh about 40 tonnes. The portal stones are about 2.3m high. The side stone is buttressed by a modern stone and concrete support. There is now no trace of any cairn material. The small stones on top of the capstone are due to a legend that a wish will be granted to anyone who throws a pebble on top of the capstone so that it stays there. Another legend says that anyone who walks three times round the dolmen will be married within a year.
About 80m ESE of the portal tomb is a very fine wedge tomb (J083110) It has a 6m long wedge-shaped gallery about 1.5m wide at the front and 1.1m wide at the back. It is closed by a single stone at the W and there is one facade stone beside this. The walls of the gallery are each represented by eight stones and a back stone is set outside the ends of the walls. There is a single roof lintel in place near the E end. There is no trace of an outer wall or cairn.