Glengarriff
O'Sullivan the Chieftain of Dunboy castle began his forced march from the woodland of Glengarriff. After his defeat and retreat from his fortress he sheltered for a time in the area known as Doire Na Fulla (The Oak Tree of the Blood). Legends will say that many of the primitive stone shelters encountered in the mountains, date from this settlement. There is no doubt however that the oak woodland, more extensive at that time, would have been an ideal base from which to regroup his forces. He left on December 31st to begin his retreat to Leitrim and it is said that his wife and young child stayed behind and sought shelter in a place known as Eagle's Nest.

O'Sullivan past Carriganass Castle, the last of the O'Sullivan castles. He travelled over the hills onto Gougane Barra. From here he had the last view of the Beara Peninsula and Bantry Bay, which is family ruled for over 400 years.

Ballingeary
When O'Sullivan Bere made his epic retreat in 1602, his first camp was An Teampaillin, Augheris, 5km north toward St. Gobnait's shrine in Ballyvourney, O'Sullivan had his misfortune to lose his horse, known as An Cearc, drowned in a place known to this day as Poll an Circe (The Hole of the Hen). Only one of the great many losses that winter.

Ballyvourney
O'Sullivan Bere rested awhile in St. Gobnait's shrine, a pilgrimage site which had been granted a papal indulgence by Pope Clement the 8th in 1601. Here they prayed for a safe journey northwards but in spite of their best endeavours they were attacked in Ullanes by a garrison from the Mac Carthaigh castle from nearby Carrig a Phuca and although the enemy were defeated. The clan lost a lot of their baggage in the skirmish. Dunhallow From Muskerry, O'Sullivan Bere travelled north east to ford the river Blackwater at Boinng Ford near Millstreet and was afforded food and hospitality by O'Keefe at Boinng Castle. Some O'Keefes attacked them nearby at Flintfield and the McCarthys of Drishane and Kilmeedy tried but failed too ambush them. They travelled north to Clonfert (Newmarket) via Maher and Derrinaturbid and were welcomed by Mc Auliffe. On hearing of a threatened attack by Barrys of Buttevant they swung east to Freemount and to Ardfinnan and the Glen of Aherlow rather than a direct approach to the River Shannon.

Ballyhoura
O'Sullivan Bere made his crossing through Ballyhoura country leading west past Kanturk and Newmarket. Here they fought their first major engagement by an English garrison assisted by the Barrys when crossing a ford near Liscarroll. The Queen's army was forced to retire through hunger and fatigue. The column had now to cross the Golden Vale to get to the safety of the Slieve Felims. At Kilmallock, the White Knight and his mercenaries attacked. They were then attacked at the rear by the previous day's assailants but succeeded in avoiding a clash. Chief town of the Golden Vale is Kilmallock, capital of the Earls of Desmond. Mercenaries of the White Knight, the Gibbons, men from Limerick City and some Crown forces, in all making up more a mob than an army, came upon O' Sullivan's host, making for the mountains. This battle may have been in the region of Knockany, Hospital or Emly. It was by far the fiercest battle that the refugees had suffered thus far.