Gently rolling scenery with fine views of the sea and hills (22, 33 or 51 miles)
Most of the historic interest is related to Christianity, either its original introduction in the 4th Century; or the bloody schisms between its various branches in later times. Coming south from the Moss of Cree, just before you enter Wigtown, you pass the Martyr's Stake where Margaret Willson was drowned by the incoming tide for refusing to renounce her religion.
Garlieston has an interesting sleepy harbour, but it was not always so. During World War 2 it was the place where the Mulbery floating harbours were tested before being used for the invasion of Europe following D day. Currently there are signs indicating that permission has been given for a harbour recreational development, but as there is currently no developer it may be a while in coming. The harbour Inn does pub food; the stone built terraced cottages at the sea front are attractive.
Just south of Garlieston, near Cruggleton Farm there's a little church which is worth looking at. It's alone in a field, surrounded by a castellated wall. It's Norman (12th century). The congregation is long gone but the little church stands there still (key at the farm).
Further along the route, an interesting diversion is to St Ninian's Cave, a short walk by a stream to a wild pebble beach. The cave doesn't look much but pilgrims have walked down here for 15 centuries. The crosses that were at the cave are now at Whithorn but visitors still make them out of driftwood.
The main historic interest on the route is at Whithorn Priory. St Ninian's mission here began in 397AD, nearly two centuries before St Columba arrived from Ireland and started the Celtic church in Iona further north. St Ninian was born and educated under the Roman Empire which still existed at this time.
Being taken round the archeological dig is full of interest, the tour will take at least an hour. You can see work being done on medieval burials and the remains of a Norse settlement. Interesting too are the superb early christian crosses in the museum. The visitor centre has a picture show telling of early pilgrims and dark age settlers.
There are three options here: a Newton Stewart to Wigtown circular route of 22 miles; a Wigtown to Isle of Whithorn circle of 33 miles; or do both together which will be 51 miles. Whichever option you take there will be fine views of the sea and hills and lots of historic interest. The roads are not particularly hilly.
From Newton Stewart cross the A75 to the A714, continue south for over a mile then turn left at a phone box signed Moss of Cree. After that the route is quite straightforward. The countryside around here is very quiet with lots of dairy farms. The towns have a special charm, Wigtown having a choice of tea rooms and bookshops and Whithorn being famous as the place from which Christianity was introduced to Scotland. Despite its name the Isle of Whithorn is part of mainland Scotland. The former island is now joined to the mainland by Harbour Row. There's a great pub the Steam Packet Inn which does good bar lunches and a little harbour with fishing boats and yachts. Nearby too is St Ninian's Chapel, the ruin of a 13th century chapel on a site traditionally associated with St Ninian. It's by the sea, a great spot for a picnic with wild flowers and views over Wigtown Bay. Five miles further along the route, an interesting diversion is to St Ninian's Cave, a short walk by a stream to a wild pebble beach.
Whithorn has a choice of tea rooms and pubs as well as a visitor centre which includes an archeological dig and museum. When the time comes to cycle back to Newton Stewart or Wigtown, bear in mind that while the inland sections of the return route have great views there are no sources of food so take something to eat and drink with you. Just before you enter Newton Stewart note that you can avoid the roundabout and most of the busy A75 by turning first left to enter the town on a minor road.