Distance: 3.5 miles

Difficulty of the terrain: medium

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

Walk from Chirbury in the far west of Shropshire, across the Vale of Montgomery, over the Offa’s Dyke National Trail and into Wales to Montgomery the former county town of Montgomeryshire.

The Story

Route Notes

Getting Back

Small but Poised

These days Montgomery, in northern Powys, a mile west of Shropshire’s border between England and Wales is essentially a large village, with around 1,300 inhabitants. However, to its residents, and in terms of its feel, it remains a town.

Montgomery grew up in the early 13th Century in the shadow of Montgomery Castle, whose ruins still command the top of a steep hill above the town, which affords views further west towards where the River Severn twists into England from Wales.

The town’s story is typical of many of the towns created by knights and nobility through royal charters during the 13th Century. Though unlike those situated further east firmly in England, Montgomery also tells the story of the medieval conflicts between England and Wales which were resolved, albeit not without ongoing tension, in 1536 when under Henry VIII, himself of Welsh descent, Wales was fully incorporated into a legal entity known to this day as England and Wales.

In common with the rest of the Welsh Marches this history defined Montgomery’s early history. The Treaty of Montgomery, where uniquely in history, Llywelyn ap Gruffudd was recognised by England’s Henry III as Prince of Wales and an independent ruler in his own right, was signed at Montgomery Castle in 1267. Later in the early 15th Century Montgomery was looted by supporters of Owain Glyndŵr.

After the Parliamentary side won the initial phases of the mid-17th Century Civil Wars, Montgomery Castle was slighted, with its defensive walls breached and its roof removed, to ensure it could no longer be used for defensive purposes. 

From that date Montgomery settled into being the sleepy county town for the sparsely populated mid-Welsh county of Montgomeryshire. Many of the town’s grandest civic buildings like the town hall were constructed in the 18th and 19th Century, including its spectacular red brick Town Hall built between 1748 and 1751. As well as the remains of the old Montgomeryshire County Goal, which was constructed in the era of social reform in the early 1830s, around the time that the work house system replaced the Old Poor Law, and had a relatively short life, closing in 1878, with most of the structure demolished.

While Montgomeryshire ceased to exist at local government reorganisation in 1974, with Montgomery becoming part of the large mid-Wales county of Powys, it remains a key district centre to this day. The town retains an unusually large proportion of its original 13th Century street plan, with the historic centre home to numerous buildings like the Old Bell, a former pub which is now a museum, dating back to the 16th Century. While for a settlement of its relatively small size, and tranquility, Montgomery retains a relatively large number of shops, a post office, several cafes, a chip shop and a few pubs. Which is a fairly substantial number of amenities for a settlement with fewer than 1,500 inhabitants.

Route Notes

Get the route: via Ordnance Survey Maps or download the GPX. file from Dropbox

I create the Walk Midlands routes via Ordnance Survey Maps Explorer enabling me to take them on my phone. Subscribe yourself via the banner above.

On alighting the bus in the centre of Chirbury, to the east of the Vale of Montgomery, head to the crossroads in the centre of the village.

Here head west down a quiet lane beside a large sturdy redbrick late Victorian house heading out of the village.

Continue along this lane for some distance.

Soon on the right there is a footpath waymark pointing up a green lane, and through a metal gate out into open fields.

Follow this path across the fields approaching a small cluster of houses.

Head up the driveway of these properties and then turn right onto a footpath across the fields.

Soon you approach a stand of trees, where you pick up the Offa’s Dyke Path National Trail.

Upon reaching the Offa’s Dyke footpath, turn right.

Soon you turn left down a footpath on the far side of a stile, crossing from the English Midlands into Mid-Wales, approaching Montgomery which is now in the middle distance.

When you reach a little cottage turn right, and head uphill, until beside a larger house you reach a lane.

Turn left and follow this lane around towards Montgomery.

Soon you turn left up a wide footpath approaching a modern housing estate on the edge of Montgomery.

Walk through the housing estate and head up a flight of steps towards the town’s church.

Soon you reach the main road through the town where you turn left to reach the main square (currently primarily a car park) where the Town Hall stands at the far end.

Behind the Town Hall there is a steep, narrow road which runs uphill towards the ruins of Montgomery Castle with its commanding views across the plains below.

Montgomery town centre is where the walk ends.

Getting Back

At the time of writing in November 2025 Montgomery was served by four buses a day to and from Shrewsbury on Mondays through to Saturdays with no Sunday service. Shrewsbury is a major bus hub for destinations across Shropshire and the surrounding counties as well as being served by trains south towards Hereford and South Wales, west towards the West midlands conurbation, and north towards North Wales, Crewe and Manchester. Two additional services run between Montgomery and Shrewsbury on week days. In November 2025 Montgomery was also served by Transport for Wales bus services between Oswestry and Newtown via Welshpool. Welshpool has an hourly train service on weekdays and Saturdays north west to Shrewsbury.