There are many historic market towns and villages along our eastern border as it winds its way from the southern Wye Valley towards the North Wales coastline, often following the Offa’s Dyke walking path. The historic markets are often a legacy as to how the towns have developed over the centuries and still today these towns are a centre for local life – so a great way for your clients to meet the locals! 

Day one

Start the tour in Chepstow, dating back to medieval times. This market town is still as famous for horseracing which can be seen at Chepstow Racecourse, and its Norman castle dramatically located perched high above the banks of the River Wye. Chepstow Castle is reputed to be the first stone built castle in Britain and marks the gateway into Wales.

Continue on the scenic A486 towards the county town of Monmouth. En-route, there’s the opportunity to visit the ruins of Tintern Abbey. It was a popular location for late 18th Century landscape painters including JMW Turner. Recently, this ‘Cistercian Abbey’ has seen a major two-year programme of conservation work that included the iconic 13th-century west front, it is regarded as one of the great glories of Gothic architecture in Britain. There is a produce market in the village on the second Saturday of each month between 10:00 and 14:00.

Tintern Abbey is in the care of Cadw. Register with the Cadw Tour Operator Scheme (CTOS) to become a member of Cadw’s online group booking scheme. Members benefit from preferential trade rates and discounts, complimentary admission for your tour leader, complimentary introductions to Cadw monuments, enhanced information for existing tours and invoicing following your visit. Travel Trade Explorer Passes can also be purchased. Please contact

An aerial shot of Chepstow Castle with a shadowy reflection in the River Wye.
Aerial shot of the grand ruins of Tintern Abbey.

Chepstow Castle and Tintern Abbey

In Monmouth, wander along the main shopping street that has retained many of its Georgian buildings, but a ‘must see’ is the 13th century stone-gated bridge that crosses the River Monnow - it is the only remaining medieval fortified river bridge in Great Britain. A general market takes place on Fridays and Saturdays every week outside Shire Hall, but may be subject to change if a large wedding is taking place.

Enjoy lunch in one of the pubs, cafes or restaurants before continuing to the medieval market town of Hay-on-Wye, a world centre for antiquarian books which also hosts the annual Hay Festival in May/June which has placed the town well and truly on the world literary map. Hay Castle has opened to the public for the first time in 900 years following a 10 year restoration and renovation project.

Alternatively, if your clients are looking for an activity filled afternoon, Inspire2Adventure offer a range of water sports and  dry sports along the River Wye.

Approximate distance: 63 miles (100km)

Approximate driving time: 1hr 15min



Superior Bedroom

The Swan at Hay

Llangoed Hall

Llangoed Hall


The Metropole Hotel

Llandrindod Wells

Day two

Today begins with a scenic drive following the A481 / A44 / B4357 to Presteigne a town with a large number of half-timbered black and white buildings and good pubs. There is a self-guided audio tour of the apartment at The Judge’s Lodging that also includes the cells and former law courts giving a flavour for life in the 1870s. Rates are available for groups of 10 or more.

Underground whitewashed tunnels of the prison area at The Judge's Lodging.

The Judge's Lodging

Returning inland on the A488, continue northwards on the A483 to the pretty town of Montgomery to explore its remarkably unchanged Georgian main square. Walk up to the castle’s ruins to see some breathtaking views of the surrounding countryside.

After lunch, continue to Welshpool, a gateway for travellers entering and leaving Wales for countless centuries. This active, bustling town is at its best on Mondays, when local farmers gather for the lifestock market including cattle and lambs and trading has been taking place on a similar basis since 1263. Explore its many well-preserved old buildings and then take a trip on the narrow gauge Welshpool & Llanfair Light Railway. It links the market town of Welshpool to the rural community of Llanfair Caereinion. Being a narrow gauge, it allows for tight curves and steep gradients, so the train is able to follow the direction of the countryside. Discounts are available for groups of 10 or more paying adults / senior citizens. Alternatively, take a relaxing boat trip on the Montgomery Canal. It was originally planned to run from Llanymynech to Newtown for the transportation of limestone for agricultural purposes. Boat trips run every Sunday and Bank Holiday (with a couple of exceptions) from Easter to the end of September. Private trips can also be accommodated by arrangement.

Approximate distance: 48 miles (77km)

Approximate driving time: 1hr 15min

A man cycling along the footpath alongside the Montgomery Canal near Welshpool.
Locomotive passing through countryside on the Welshpool and Llanfair light railway.

Montgomery Canal, and Welshpool and Llanfair railway


Spa Facilities

The Hand at Llanarmon

Lake Vyrnwy Hotel & Spa

Lake Vyrnwy Hotel & Spa

Lake Vyrnwy
Pale Hall Hotel

Pale Hall Hotel

Accessible bedroom - Ramada Plaza Wrexham

Ramada Plaza by Wyndham Wrexham


Day three

Begin the day at Chirk Castle. Like the World Heritage Site castles of Conwy, Caernarfon, Harlech and Beaumaris it was built during the reign of Edward I but it is the last castle from this period that is still lived in today, complete with luxurious interiors. The state rooms include a 17th century long gallery, grand 18th century saloon with rich tapestries, and the restored ‘East Range’, containing the library and 1920s style Bow Room highlighting the connections to high society.

The gardens cover 5.5 acres of manicured lawns, clipped yews, herbaceous borders, beautiful rose, shrub and rock gardens. There are also 480 acres of estate parkland to explore. Group rates are available for pre booked groups. 7 and 14 day touring passes are also available for international visitors.

Enroute to Llangollen is the Pontcysyllte Aqueduct - a spectacular piece of engineering, completed in the 19th century to carry the canal over the River Dee. This is the largest aqueduct in Britain and the work was undertaken by Thomas Telford. The structure is 307m long, 38m high and holds 1.5 million litres of water. It was recently included in TripAdvisor’s 10 heat-pumping places to visit. Your clients can either walk across the aqueduct (allow 45 minutes round trip from the coach park at Queens Street, Cefn Mawr, LL14 3NP) or take a leisurely canal boat ride. Depending on time, options include a 45 minute trip or a longer two hour chartered boat trips for groups. Anglo Welsh Waterways Holidays offer narrow boat trips in the 'Seren Fach' five times daily, seven days a week.

Llangollen is beautifully surrounded by Berwyn mountains and forests. A small general market takes place every Tuesday in the Market Street car park. On Friday mornings between March and December there is a country market with local produce including cakes, honey and jams and crafts and there is even a song entitled ‘Llangollen Market’! 

The town has been made famous by the annual July festival ‘Llangollen International Musical Eisteddfod’ established after the Second World War to encourage peace between nations.

Llangollen Railway travels 10 miles to Corwen along the Dee Valley, an Area of Outstanding Natural Beauty. On-board dining is available including Welsh cream tea, picnic, buffet lunches and afternoon tea. There is also a Café bar and gift shop at Llangollen Station and a tea room at Carrog Station. Group discount offered for 15 or more passengers. Discount increases if more than 35. Free admission for coach driver or tour guide.

Aerial shot of Chirk Castle nestled in trees, with the valley beyond.
A canal boat travelling along the Pontcysyllte Aqueduct with people walking along the footpath.
View of Llangollen bridge leading into the town from the river Dee.

Chirk Castle, Pontcysyllte Aqueduct, Llangollen

Other things to do include:

Look out for Castell Dinas Brân. A hill overlooking the town with a ruined castle at the top, it is rumoured that The Holy Grail is buried here. If your clients are feeling energetic they can walk to see the ruins of Castell Dinas Brȃn and enjoy lovely views. A round trip is 4 miles or 6.5km (or longer if you search for the Holy Grail).

The stone ruins of Castell Dinas Bran.

Castell Dinas Brân

Plas Newydd House and Garden is a black and white timber framed house home to the ‘infamous’ Ladies of Llangollen. For groups of 15 or more they offer a complimentary introduction by one of their Heritage Assistants. The Old Dairy Café is on site offering refreshments.

If time permits, finish the tour with a scenic drive on the A452 along the Horseshoe Pass (1367ft/417m) which offers unsurpassed views in all directions.

Approximate distance: 28 miles/45 km

Approximate driving time: 47min

Are you interested in the story of the Ladies of Llangollen? Throughout the day we have multiple heritage talks sharing...

Posted by Plas Newydd on Tuesday, September 21, 2021

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