A 12.6 mile circular walk around Oswestry, highlighting the rich heritage including the Old Oswestry Hillfort.

Oswald’s Trail image


12.6 miles


Undulating countryside

Start from

Oswestry Bus Station

Nearest to




The route

Oswald’s Trail is a complete circuit of Oswestry taking in many of the important historical points of interest along the way. Whilst the total route is 12.6 miles it has been divided into 5 easily accomplished sections so that the walk can be undertaken in stages.

Oswald’s Trail was conceived by the Oswestry Group of the Ramblers as a permanent mark of the group having been in existence for 40 years (2013), with the support and help of The Ramblers Holidays Charitable Trust, The Ramblers and Shropshire Council.

History of Oswald

The Battle of Maserfield is thought to have been fought near Oswestry in 642, between the Anglo-Saxon kings Penda of Mercia and Oswald of Northumbria. Oswald was killed in this battle was dismembered and according to legend, one of his arms was carried to an ash tree by a raven.  Miracles were subsequently attributed to the tree as Oswald was considered a saint. Thus it is believed that the name of the site is derived from a reference to “Oswald’s Tree”. The spring Oswald’s Well is supposed to have originated where the bird dropped the arm from the tree.

Oswestry Hill Fort

Old Oswestry is one of Britain’s most spectacular and impressive early Iron Age hill forts in the Welsh Marches near Oswestry in north west Shropshire. Old Oswestry Hillfort is reputed as “The Stonehenge of the Iron Age Period”.  It remains one of the best preserved hill forts in the UK, according to English Heritage. Built on lower ground, it is also one of the most accessible hill forts with stunning panoramic views across North Wales, Cheshire and Shropshire.

Wat’s Dyke

Wat’s Dyke is a 40 mile (64 km) earthwork running through the northern Welsh Marches from Basingwerk Abbey on the River Dee estuary, passing to the east of Oswestry and on to Maesbury in Shropshire, England. It runs generally parallel to Offa’s Dyke, sometimes within a few yards but never more than three miles away. The Wat’s Dyke Way follows the dyke for 61 miles.

Oswestry Old Racecourse Common

The site stands on the 1000ft hilltop of Cyrn y Bwch (Welsh for ‘Horns of the Buck’) which was historically seen as the barrier between “the Kingdom and the Principality”. Thus it has viewpoints giving excellent vistas over England and Wales.  The site provides extensive views of the surrounding countryside. Consisting of a patchwork of scrub, scattered trees, bracken and wildflower rich grassland the area supports a wide range of birds and insects.  By the eighteenth century the area was being used for racing horses, with one of the reasons for the race meetings being to bring together the local landowners and gentry of Wales and England.  Signs of this historic use are still evident. Much of the figure of eight racetrack forms the main walking route around the site. The remains of the grandstand are still present. For more information please see our Oswestry Old Racecourse Common page.

Offa’s Dyke Path National Trail

The Offa’s Dyke Path National Trail runs for a distance of 285Km (177miles) following the English-Welsh border as it progresses from Chepstow on the Severn Estuary to Prestatyn on the north Wales coast.  45Km (28miles) of the route passes through Shropshire with a section passing through the woods and common of Oswestry’s old racecourse.


Oswestry is an ancient market town located in the North of Shropshire close by the English - Welsh Border. Its strategic position as a 'frontier town' has given it a turbulent history. Today the town still retains its vital function as a market and shopping centre serving North West Shropshire and Mid Wales. The narrow passageways link streets whose names conjure up images of the past: English Walls, Welsh Walls, The Bailey and the Horsemarket. It is a locally important shopping and agricultural centre and still retains the intimacy of a rural town serving local people and home to a number of specialist and independent shops.