The first site visited was Castle Caulfield (H755626). Here there are substantial remains of a large house, built by Sir Toby Caulfield between 1611 and 1619, on the site of an earlier O'Donnelly castle. A joist from one of the walls was dendro-dated to about 1282 and may belong to this earlier fort. The oldest part of the existing building is the gatehouse which has Tudor-style doorways, murder-holes and gun-loops. The Caulfield arms appear over the entrance. This is the only defensible part of the castle. The main house was originally half H in plan but the NW wing is now missing leaving an L-shaped ruin. The building is three storeys high with attics, with many large mullioned windows and tall chimney stacks.
The castle was burned in the rebellion of 1651 but was repaired and re-occupied by the Caulfields until the 1660s. St Oliver Plunkett is known to have held a service at the castle in 1670 and John Wesley preached there in 1767.
About 3km NNE of Castlecaulfield is Donaghmore (H789654). The monastery here was supposedly founded by St Patrick who left Colum in charge. The Bell of Clogher, which is associated with the monastery, is now in the National Museum, Dublin. The churches and refectory were burned in 1195 and it was a parish church in 1306. The ruins of the old church were still standing in the 19th century, but there are now no visible remains.
Just outside the graveyard wall is a very fine High Cross. It is made up of parts from two crosses, or possibly it is one cross with the central part of the shaft missing. It is richly decorated with biblical scenes. On the east side the New Testament subjects include the Annunciation to the Shepherds, the Adoration of the Magi, the Baptism of Christ, the Miracle at Cana, the Multiplication of the Loaves and Fishes, and the Crucifixion. On the west side are the Fall of Man, Cain and Abel, and the Sacrifice of Isaac. The Cain and Abel is unusual in that it shows three figures. The third figure may represent Christ. It probably dates from the 10th century. It is said to have been thrown down in the 17th century and re-erected in the 18th century.
In the graveyard beside the cross is a modern copy recently erected by the local history society. It is a very fine cross which makes interpretation of the original very easy. Close to the centre of the graveyard is a mature hawthorn tree. At the base is a large boulder with a deep bullaun.
About 5km ENE of Donaghmore is Newmills (H815676). The modern Church of Ireland church is on the site of a medievel parish church and possibly a pre-Norman site. Close to the church is a large boulder with two bullauns.
Excavation uncovered post and stakeholes from a round house of Early Christian date with an enclosing ditch. Twigs from the lowest layer of the ditch gave a radiocarbon date of 615-885 AD. A second ditch seemed to form part of an angular enclosure and several sherds of everted rim ware came from it. Another item of interest in the graveyard is a rectangular gravestone with a skull-and-crossbones. There is a raised letter inscription around the edge. However the stone is partly covered with moss and leaf mould and would require cleaning before all the inscription could be read.
2km to the south of Cookstown is Loughry College. A wedge-tomb (H812749) sits on the summit of a glacial knoll in the grounds of the college. There is a rectangular gallery 7.6m long by 1.5m wide, formed by 11 limestone sidestones. It is orientated E-W and there is a single backstone at the east end.
Two large capstones remain in situ, resting on the first two matching pairs of sidestones. The outer walling is represented by three stones at the north side and one stone at the south. The remains of the facade at the west end may be interpreted from three remaining stones. There is no trace of the original cairn. The protective fence has allowed the growth of weeds and long grass which masks some of the detail.
Just to the east of Cookstown is Killymoon Golf Club. One of several thickets in the middle of the golf course hides the remains of a court tomb (H823768). It lies on relatively flat ground, on a limestone outcrop. The cairn area is represented by a roughly oblong spread of stones about 45m by 35m.
Within this area are 12 large stones which form a horseshoe-shaped chamber 10m long by 4m wide, with 2 outlying stones at iis east end, all aligned on an E-W axis. There is a great deal of smaller cairn material but much of this is probably land clearance associated with the construction of the golf course.
About 9km to the east of Cookstown and a short distance NW of Coagh is a dolmen (H886790). This portal tomb, in Tamlaght townland, is known locally as the Cloghtogle. It is set in a hedge on the south side of a minor road with a modern water tank close to the south edge.
The proximity of the water tank and the fact that the monument is overgrown with thorn and ivy makes interpretation and photographing of the dolmen very difficult. The tomb consists of a massive rounded capstone set on four supporting stones with other loose stones scattered below and around. The capstone slopes W-E and is 1.6m high by 2.8m long and 2.2m thick. The supporting stones are respectively 1.05m high, 1.15m high, 0.95m high and 0.8m high.
A further 8km ESE of Coagh is Arboe (or Ardboe)Monastic Site (H966756). Arboe High Cross, in Farsnagh townland, is a tall slender object with only one portion of the ring missing. The Cross is a typical Scripture Cross with many carved panels with figure sculpture.
Some panels feature geometrical and other decoration. Many of the panels are greatly weathererd and unclear. A decorated band encircles the shaft about three-quarters of the way up. On the west side below the decoration are four figure panels. These show the Adoration of the Magi, the Wedding at Cana, the Miracle of the Loaves and Fishes, and the entry into Jerusalem. Above the decoration a panel with three figures possibly represents the Arrest of Christ and there is a Crucifixion at the cross. On the east side the bottom panel shows Adam & Eve. Above this is Abraham & Isaac, Daniel in the Lions' Den and the Three Hebrew Children in the Fiery Furnace. At the cross is the Last Judgement or possibly Christ in Glory. The bottom panel on the south face shows Cain & Abel.
The church nearby is a simple rectangular structure measuring 19m by 6m, with a north doorway and a pointed east and west window. There are two windows in the north and south walls. The walls are 1m thick. It probably dates from the early 17th century. The memorials in the churchyard range from 18th century to modern. One stone of 1759 is topped by a cross flanked by carved faces.
Some stones feature two winged heads and one stone has three. The graveyard is still in use. Arboe Cross marks the site of a monastery associated with St Colman and founded perhaps in the 6th century. The monastery was burned in 1166 but later emerged as a medieval church site. In a field about 200m NE of the cross is an overgrown rectangular ruin measuring about 12m by 7m. A short distance to the north are three sides of a substantial structure. These buildings may be part of the early monastic settlement.
About 15km SW of Arboe is Mountjoy Castle (H901697). It stands in Magheralamfield townland on a hill overlooking Lough Neagh. It was built by Lord Mountjoy in 1602 and partly burned in 1643.
It is a two-storey brick building and the lower storey is stone-faced on the outside. It consists of a central rectangular block with four spear-shaped angle towers with gun loops.The north-west tower is partly demolished and the west curtain wall destroyed. The entrance was on the south side of the east curtain wall. On the first floor there are some wide windows.