Day 1, Chepstow to Bigsweir Bridge

The backdrop to the start of your Offa’s Dyke journey is extremely impressive, a large stone and plaque set at the top of a steep bank provides a great photo opportunity, as indeed does the view.

Behind you lies the River Severn, here at its widest point as it opens out into the Bristol Channel, spanned by the ‘old’ Severn Bridge, with its iconic ‘H’-shaped pillars which have welcomed travellers between England and Wales for decades.

Though there is now a newer second crossing further south, this is THE view and a wonderful way to start your trip north, where you will encounter the river in a much smaller form later on.

Walking-wise, there is a bit of doubling back on yourself to get to the start-point on this remote bank but the extra distance is well worth it and as you stride back down the steep bank, you can reflect that you have started in style.

Very shortly, the path then rather less heroically goes through a small housing estate, in which is easy to get momentarily lost in but gather your bearings with confidence because Offa’s Dyke is a fantastically well-signposted route and any navigation issues you face will be few and far between.

I am terrible at map reading and have turned wandering blindly around in circles into an art form. I hardly deviated from Offa’s Dyke at all on Day 1, which tells you all you need to know about the signage.

Emerging from the housing, you find yourself following the channel of the River Wye, which meets the Severn at Chepstow and the diverging courses of those two rivers frame the Forest of Dean area.

As you cross over the main A48 and pick your way uphill through the knot of housing which is Tutshill, keep your eyes to the left and through the trees you will see a nice view of the Wye as it passes Chepstow, crossed in the distance by a small bridge and overlooked by the impressive medieval castle.

And up and up you go – there is a fair bit of climb in this first section as you gain the height above the river but it is not savage and soon you meet the line of the Gloucestershire Way, which shares a few hundred yards before the paths diverge.

Urban life is now being left behind you, you won’t really see anything similar for two days when you reach Monmouth, for now you enter a world of forest, small villages and riverbanks.

An early point of interest is the remains of a medieval watchtower just beyond Tutshill but you will really be in your stride now, the ground is levelling out and you can start to push on towards Woodcroft.

As you pass to the left of the village, there is a chance to appreciate the height you have gained as you glimpse the River Wye far below, cut into a deep channel around Wintour’s Leap, named after a Royalist who reputedly escaped his Parliamentarian pursuers during the civil war of the 1640s by leaping into the river and swimming to Chepstow Castle.


The stone marking the start/finish of Offa’s Dyke Path at Chepstow. There is a fantastic view of the River Severn as it opens into the Bristol Channel and the ‘old’ Severn Bridge from the cliff where the stone sits.

Chepstow watchtower – medieval ruin on the Offa’s Dyke Path just outside Chepstow.

Chepstow watchtower – medieval ruin on the Offa’s Dyke Path just outside Chepstow.

Up to now, you will have had the company of the odd dog-walker but now the route starts to quieten down, especially on a weekday, and there is a lovely sense of silence and isolation. Even the cows, a real feature of the early part of the walk, start to disappear as you push towards woodland.

I walked this path in early spring and despite the seasonal rains, it was in very good condition. The last remains of the autumn leaves provided a binding and it was possible to make very good time, buoyed by a warmish breeze despite overcast skies and with early primroses and daffodils offering a lovely burst of colour in the blossoming hedgerows now the snowdrops had gone.

Approaching Tintern, you start to enter woodland proper and with it another bout of steepish climb, though take heart that it will give you the height to enjoy probably the best view of this first day – the Devil’s Pulpit.

This natural viewpoint offers a lovely outlook along the Wye Valley with the exceptionally picturesque ruins of Tintern Abbey in the foreground. The ruins inspired one of the great works by the Georgian/Victorian poet William Wordsworth and will probably inspire a photograph or two for you as well.

The story goes that the Devil tried to tempt the monks of the abbey from the stone ledge but was seen off by their prayers.

There is another notable landmark before you reach the Devil’s Pulpit however – Offa’s Dyke itself, a two-mile section of which is preserved in this area.

A sign alerts you to the fact and you need it because it is not immediately apparent – more distinct sections lie later on the trail.

However, it is a nice boost to stand on this remarkable piece of civil engineering, ordered by King Offa in the 8th century to mark the boundary between his lands and the Welsh. It is worth reflecting that until the canal-building boom in the late 18th century, this was the largest single engineering undertaking in the country for some 1,000 years.

By now your legs may be pinging a bit from the up and down nature of the woodland and by Lippets Grove, I was very much thinking of lunch but I pushed on manfully to Brockweir, which I reached after about three hours’ walking from Chepstow.

In fact you have a choice just before Brockweir, there is a high road to Bigsweir via the Hudnalls or a low road along the river and you are free to take your pick.

After all the woodland, I fancied a bit of riverside so carried on down the hill to the village of Brockweir, where there are some handy benches where a tired walker can enjoy a ham sandwich in comfort. There is even a pub, which I resisted but only just.

Brockweir is a small, neat and pretty little hamlet but there is an information board on the old quayside which records that this was once a bustling concern. It was the highest point on the Wye that the freight boats could navigate and was a key point of exchange for iron and timber out of the Forest of Dean during the 18th and 19th century.

Beyond Brockweir, your walking terrain changes markedly, the high wooded ridges are behind you now and instead you transfer to flat river bank. For my spring walk, there was evidence of seasonal flooding, which I had already noted from the Devil’s Pulpit as the fields below Tintern Abbey were streaked with floodwater.

It was clear but boggy and you need to watch your feet a little. Watch out for patches of water amidst the grass as the water channels back towards the river – that’s bog!

That said, after all the up and down, it was nice to just amble on the flat and very soon you will see the village of Llandogo on the opposite bank. A meandering turn in the river takes us to Bigsweir and in the short distance, there is the bridge which is today’s goal.

It is not a brutal day’s walking by any means but your legs will be tired by now. Llandogo is about a 20 minute walk by road but it is not too bad – there are accommodation options here and also a pub, The Sloop. Rest up for tomorrow – we are off to Monmouth!

Left – A view of Tintern Abbey ruins and the River Wye from the Devil’s Pulpit, where legend says the Devil preached at the monks to try and tempt them away from their faith.


Right – The riverside section towards the end of the day sees Llandogo on the opposite bank near the finish point at Bigsweir Bridge