01694 723600 info@secrethillswalking.co.uk

Offa’s Country- West Shropshire and East Powys

The tour is not available yet.

Proceed Booking

Save To Wish List

Adding item to wishlist requires an account


Why Book With Us?

  • Value for Money
  • Personal Service
  • Hand-picked Tours & Activities
  • No single supplement (UK only)
  • Flights from local airports (Europe only)

Make an Enquiry

Do not hesitate to contact us. We are an expert team and we are always happy to talk to you.


01694 723600

You matter to us & we promise to provide you with a superb walking & social holiday, tailored specifically to your needs. We provide walking holidays for walkers & as walkers ourselves, we appreciate & understand the requirements of a walking holiday.

Discover a borderland full of history, with castles, canals, spectacular bridges and bustling market towns. Watch out for badgers and birds of prey. Our solos guided walking holiday introduces you to the stunning, secret lands of the Welsh borders and west Shropshire. It is a land which is undiscovered, where you may walk for miles without encountering anybody else on your path. If you want to get away from the hustle and bustle of life, then this is the holiday for you.

Join us on our speciality holidays – aimed uniquely at singles and solos. We offer guided walking holidays in some of the most picturesque locations in the UK and Europe. We also specialise in providing bespoke guided walking holidays for specific groups.

  • Four and a half days
  • Refund guarantee
  • Expert Tour Guides
  • Five days
  • Location: Shropshire Hills
What you get on a Secret Hills Break
  • Hotel bed and breakfast– en suite two nights/ three nights if the holiday falls on a Bank Holiday – Spring Bank or August Bank Holiday
  • Dinner- three course.
  • Lunch- except first day
  • Sole Occupancy
  • Personal service
  • Expert guiding- friendly, local guides that know the area superbly well
  • Transport to walks start and finish as needed
  • Flexibility
  • No single supplement
  • A social, relaxed approach
  • Full joining details prior to your holiday
  • Our administration support from the point of booking to you joining the holiday

Hotel and Meals

We base this holiday at Montgomery – once county town of Montgomeryshire- a lovely setting for walking the borderlands between England and Wales.

Our hotel is the Dragon in the market square- a half timbered building and a hotel for decades.  Welcoming, homely yet efficiently run by its local owners. Comfortable lounges and a well stocked bar. Every room is different too. There is a swimming pool on site for your use.


Breakfast and dinner at the hotel. We will try to stop at one of our lovely country pubs at lunch time but it may aslo be a packed lunch.

Great reasons to join us

There are other walking holiday companies that cover the countryside but we believe we offer the best value for many reasons….

  • We specialise in organising guided walking holidays for single and solos travellers
  • We are a small friendly company
  • We have a loyal customer base who return again and again (so we must be doing something right) – read our testimonials page on the website
  • We offer a lot of flexibility – you can stay extra nights which we are happy to organise for you. We are also very flexible on the walks we provide, adapting to suit walkers and weather conditions
  • Our walk leading is second to none. Unlike some other large Walking Companies, we use LOCAL leaders who live in the area and who love their surroundings. They have expert knowledge of everything you need to know to make an area come alive.
  • You are safe in our hands – our guides are experts, fully qualified in first aid. Also, because of their local knowledge of the hills, they can respond to any situation that might for example demand cutting short a route. They don’t need to consult maps – they know the hills intimately.
  • Our leaders are all easy-going, genuinely sociable people who want to ensure that you have the best time you can with the rest of the group. They make the weekend fun by engaging with all members of a group, and ensuring that everyone feels part of the group experience.
  • We give great value for money. Because we recognise that lots of walkers holiday on their own, we have negotiated no single supplement deals with all our hotels to ensure the best possible deal.
  • We always use good hotels. 
  • We have smaller groups than some of the larger walking companies, because we believe the social experience is much better in a smaller group. People can talk to everyone, especially at dinner where you can all sit on one table in a small group. Our numbers vary from holiday to holiday but an average group size would be 8-12.


Montgomery is close to the borders of England and Wales.

SY15 6PA for your Sat Nav.

The nearest rail station is Welshpool. See www.nationalrail.co.uk

The re are taxis available from this station.


We start walking on Sunday afternoon at 2.30pm- a short two hour walk to enable you to get to know each other and ourselves.Solos and Singles Guided walking in the Shropshire Hills

Four day walks of between 9 and 11 miles and on the first afternoon a lovely get to know you walk around the town and surrounding countryside.

We will finish at about 3.30pm on the last day.

Grade and Difficulty

The countryside around Montgomery is mainly rolling hills and moors, with deep valleys.

The walking is moderate with some steep ascents and descents, but we will take these steadily.

We walk between 9 and 11 miles a day. Footpaths are generally good and well marked. The underfoot conditions can be stony- so you need good, well soled walking boots for this holiday.

You may find that walking poles will aid your enjoyment of this land.


Although our leaders are well trained and experienced in dealing with different capabilities of our walking clients, if they have any concerns about any clients ability or suitability to undertake safely any walking activity we plan or they feel that participation of an individual may affect the groups safety and cohesion, then they have full permission to exclude that client from an activity.

They will try at all times to provide an alternative suggested activity, though this may involve the client in additional local cost.

We rarely have to enforce this above recommendation, but it is a sensible and necessary protection for the individual client, the group and the leaders.

Sample Walks

Walks in the following areas

– Montgomery’s hinterland- its fort and memorial on the hill, Offa’s Dyke and the lovely surrounding countryside of rolling hillsSolo and Singles Guided walking in the Shropshire Hills

– the Severn Valley, Welshpool and the Montgomery canal.

– The iconic Stiperstones ridge in West Shropshire.

– Corndon and Roundton hills in East Powys.

– Offa’s Dyke country and Kerry Ridgway.

– The wild moorlands of the Clun Forest area where Offa’s Dyke crosses Llanfair Hill.

– Around the lovely market town of Bishops Castle and the Shropshire Way.

Walking at a steady pace – time to take in the broad expanse of green countryside

Meet New Friends

Its all about meeting new friends. Each holiday is designed to be a friendly, relaxed and stress free occasion. Talking is as important as walking on Secrethills Walking Holidays. We don’t go in for discos, we may use an event that is taking place in the area we are in to boost the weekends activities – but its good, old fashioned chat that makes our short breaks successful.

“Make new friends that turn into old friends” – that’s our motto.

You might be surprised by what fun you’ll have with people who are older or younger than you during a holiday with us, and that’s exactly the sort of atmosphere we encourage; people find it very rewarding. It doesn’t matter what your reasons for traveling with us are, we’ve had people who are single, divorced or widowed, people who have partners that are unable to travel, and people who can’t holiday with their friends anymore as they’ve all got married themselves. There are people who want to make friends, see sights, and experience something completely new. Whatever your reason, we’ll welcome you with open arms and our friendly hosts will help you to get the most out of your holiday.

Don’t worry if this is the first time you have ventured to join a group holiday – its always a bit daunting – but we will look after you and ensure that you get used to being amongst friends again. Trust us to to get you back into the swing of things.

Oh – by the way – its not a dating agency – over the years we have had people meet and fall in love – but that’s just chance. Our aim is that you make like minded friends – just relax and enjoy.

Just arrive and enjoy.

How to Book

To reserve a place on any of our holidays, please follow these simple instructions.

Reserve online  – once you have chosen your holiday, click on Proceed Booking and complete the online form. If you have difficulty reserving online, please  contact us (tel: 01694 723600, email: info@secrethillswalking.co.uk) and we will assist you to complete your booking.


Please note we cannot take credit/debit card details over the phone. You may pay by the following methods when you book online…

  • Paypal – if you have a Paypal account, simply click on the link to the Paypal website.
  • Credit / Debit card – we use Paypal to host our credit/debit cards facility because it is a very secure system. So if you want to pay with a card, simply click on this option which will take you to our page on the PayPal website. Check in there as a “Guest” to enable your card payment. You do not need to have a Paypal account for this transaction.
  • We will also accept a Bank Transfer – you will find our account details on the booking form.
  • Finally, we will also accept a cheque payable to Secret Hills Walking Holidays and sent to: Secret Hills Walking Holidays, 35 Sandford Avenue, Church Stretton, Shropshire, SY6 6BH

Please note than an initial deposit is required with each booking regardless of which payment method you choose. Your booking will be accepted when your payment (deposit or full balance) is received. Note – if you are reserving a holiday within a month of the start date then the full amount is due immediately and no deposit should be paid.

It is important that you read the terms and conditions before you sign the booking form.

Note – if you are reserving a holiday within a month of the start date then the full amount is due immediately and no deposit should be paid.


Montgomery, in Welsh, Trefaldwyn, meaning “The Town of Baldwin”  is a small town with a big history. The town of nearly 1,300 people is situated in the Welsh Marches, (the lands along the English and Welsh border) and Iron Age Celts, the Romans, the Saxons, the Normans, the English Civil War and many other historical forces all left their mark here.Solos and Singles Guided walking in Offa's Country

Fast forward to the 21st century and Montgomery, a Georgian gem, is tucked away from the madding crowds, but just 3 miles from the A483. With its medieval street layout, imposing Town Hall, mix of Georgian, Victorian and timber framed buildings and an active and generous community, it’s a place where time seems to stand still. And, with a wealth of comfortable and friendly places to stay, as well as to eat and drink, you can be sure of a warm welcome in the town.

Tickle your taste buds in one of the town’s quaint cafes selling delicious homemade cakes and locally made produce. Alternatively, dine at the hotel with its award-winning bistro restaurant or opt for a tasty bar meal served with a local beer. No time to stop? Then pick up some crispy fish ‘n chips on the go. And – if you fancy a tipple – we can do that too! Montgomery is blessed with a brewery, vineyards and local cider producers.

Fancy a little retail therapy? Then take a stroll around the local shops offering gifts, fashion, home interior wares, books and flowers. Oh, and we have a traditional ironmonger too selling everything you could ever need. A must-see attraction in its own right – you’ll travel back in time when you step through the door.

The Welsh Marches – the land we walk on this holiday



What are the Welsh Marches?

The Welsh Marches is an area that lies along the border between the countries of England and Wales, roughly between the Welsh mountains and English rivers. These borderlands don’t have an official or legal status today. The region is very picturesque; made up of mountains, rivers and valleys, quaint villages and many castles. The marches have the largest number of motte-and-bailey castles in Britain.

Why are the Welsh Marches so called?

The term, “Welsh March”, known in Latin as ‘Marchia Wallie’, comes from the Middle Ages, when “march” or “mark” was the word for a borderland or a border between two different countries/states or zones. The word “mark” comes from the Anglo-Saxon ‘mearc’ which meant boundary. The Lords who oversaw the marches were known as Marcher Lords.

Where are the Welsh Marches?

The Welsh Marches refers to the English counties that are along the border to Wales, like Shropshire and Herefordshire. At one time the Marches included Cheshire, Worcestershire and Gloucestershire as well. The Welsh Marches has the largest collection of castles than anywhere else in the UK. Some historic sites you can find include Ludlow Castle, Stokesay Castle, Hopton Castle, Wigmore Castle and Shrewsbury Castle.

What was the strategic importance of the Welsh Marches?

The Marches were used as a political tool in that they gave warning in case of a military uprising or acted as an area to check on trade between the two countries. The March Lords were able to build their own castles without permission from the King and create their own taxes for the people living in the area. The Welsh Marches became a powerful tool in the ruling of England over Wales.

What is the history of the Welsh Marches?

After the fall of the Roman rule over Britain, Wales was not the country it is known as today. Instead, it was made up of lots of small kingdoms. Each ruled by their own Prince.

Mercia, which is now known as the Midlands in England, ruled by a seventh century King called Penda, created a strong alliance with the Welsh rulers. However, after Penda’s death, his successors wanted to expand Mercia into the west. Under the leadership of King Offa, market towns like Shrewsbury and Hereford created the first barricade, Offa’s Dyke. This Dyke became a frontier between England and Wales, and can still be seen near today’s border.

King William, after the Norman Conquest, had three of his most trusted men placed in Shrewsbury and Hereford to help maintain the Welsh border and contain the Welsh people. The amount of March Lords increased over the years; raiding areas of Wales and then fortifying it against attack, giving more land to their supporters.

The March Lords created their own independent area with their own laws. By the 12th century, the marches, covered about two thirds of Wales. Hundreds of castles were built in the area by Norman lords. New towns were established in south Wales including Ludlow, Chepstow and Monmouth, but the Welsh people kept attacking and supporting rebellions against the Normans.

The Council of Wales and the Marches was started in 1472 by Edward IV, and run from Ludlow Castle. Their job was to govern the lands for the English crown.

Ludlow is a historic town that is in the centre of the Welsh border. Due to having its own castle and the size of the town, it became the authoritative capital of the Welsh Marches. This importance helped grow Ludlow’s wealth, which can still be seen today in the beautiful homes and buildings which would house many Lords and Councillors. In 1542 the Council gained more of its own powers, following on from the death of Edward IV, being now responsible for all of Wales as well as the Welsh Marches. In 1689 the Council was terminated, following William III’s claim to the throne. There was little resistance from the people, but this also led to Ludlow Castle no longer being used and falling into disrepair.

The Welsh Marches Today

Also known as just the Marches, they are used to describe the English counties along the border of Wales, including Shropshire and Herefordshire. It can also be applied to Powys, Monmouthshire and Wrexham. The Marches has a railway track, called the Welsh Marches Line, that runs from Newport in south Wales up to Shrewsbury, linking the south of Wales to the northwest region of England. 

Many tourists take the Welsh marches route for the landmarks, cities and towns that feature along the way. These include:

  • Hereford – an ancient Cathedral city, which also has a covered market, Cathedral Green, Norman arches and the 14th-century Mappa Mundi “Map of the World,” the largest medieval chained library in Europe.
  • Ludlow – Offa’s Dyke is near the town, as well as the once powerful Wigmore Castle.Ludlow also has a market, which sells many types of food, and has a lot of historical buildings still intact and being used. There’s also Ludlow Castle, former home of the Council of the Marches.
  • Shrewsbury – a town that is very rooted in its countryside and farming traditions, it still has a lot of medieval street and architectural features, with over 650 listed buildings. There’s also parks, Shrewsbury Abbey and Shrewsbury Castle.
  • Ironbridge Gorge – the birthplace of the Industrial Revolution, with 10 museums and the world’s first iron bridge.
  • Wroxeter – the third-largest Roman city in Britain, once called Viroconium.
  • Llangollen – a Welsh market town set in the mountains, it annually hosts a famous International Musical Eisteddfod.
  • Chester – Another cathedral city that was originally a Roman fort in 79 AD. Also, one of the most walled cities in Britain.




6 Reviews
Sort By:RatingDate

Carol kenny

Solo Traveller

The hotel was good with clean room, friendly staff and good food. The walk leaders were very friendly and knowledgeable providing a pleasant experience. It was well organized.

September 24, 2021

Jane Wright

Solo Traveller

  Efficient reservation. Hotel was excellent. Mike and Lynda (walk leaders) looked after us well and managed to gel us into a group quickly. An enjoyable, interesting week. Really lucky with the weather. I’m glad I did my training 🙂

September 22, 2021

Andrew Cook

Solo Traveller

Guided walking, Yes I did enjoy. Mike and Linda guided us really well and helped us if we needed helping. It was a fast pace we went but I understand that because we had to cover a lot of mileage in 1 day.  Organisation of holiday was good considering the demands of social distancing. I’m glad it went ahead. I would absolutely reserve another holiday.

September 22, 2021

Liz Watson

Solo Traveller

Alan and the walk leaders did a great job making the holiday a success.

September 28, 2020

Christine Collins

Solo Traveller

Thank you for a great walking experience with lovely people and Mike our guide who was really knowledgeable about the area we were walking though.  A great first guided walking holiday! The Dragon Inn in Montgomery could not be faulted.  The staff were attentive, helpful and polite and the food was amazing. Organisation – It was 100%, thank you.

September 24, 2020