Getting Lost on Oswald’s Trail

Oswald’s Trail is supposed to be a 13 mile circular hiking trail that takes you through the main town of Oswestry and out into the hilly rural areas near the Welsh border, passing key points of interest along the way. I say “supposed to be” as Callum and I (2/3 of The Travel Cult) got lost on several occasions and ended up walking over 19 miles. Callum is tall and has long legs and a quick pace on him. If you have read Callum’s previous blogs such as “Dublin Mountains Way” and “The Camino: A Day on the Road“, you’ll know he is a sucker for extreme distance walking, so 19 miles for him was not a significant distance. I consider myself fairly fit but keeping up with Callum was no mean feat. The fact that I completed it with him was certainly an achievement I feel merits one of those medals people get for running a marathon or trail run!

Callum and I met in Oswestry town centre. Oswestry is a small market town in Shropshire bordering with Wales where I lived from the age of 16 for many years with my family and where my mama and bro continue to live. As a young person I did not appreciate the history and beauty of the town and countryside but have since, particularly during lockdown, enjoyed exploring and learning more about it. As a ‘border town’, it has a turbulent and bloody history. The Oswestry castle “L’oeuvre” is in ruins and dates back to 1086. Much of the town centre is a conservation area due to the historical architecture including impressive timber framed Tudor style buildings as well as Georgian and Victorian buildings.

The Oswald’s trail was created by the Oswestry Group of Ramblers in 2013 marking its 40th year and is popular with local ramblers as well as those coming from further afield. So who was Oswald? King Oswald of Northumbria was born in 604, and crowned king of Northumbria at the age of 30. He died 8 years later at the Battle of Maserfield in 642, where he lost to the Anglo-Saxon King Penda of Mercia. Upon his death his body was dismembered and according to local legend, an eagle took off with one of his arms and dropped it at an ash tree where a spring miraculously emerged and continues to bubble to this day. He has since been venerated as a Saint. It is believed that the name of the town is derived from a reference to “Oswald’s Tree”. You can visit the spring which is now a restored medieval well and a lovely quiet spot where you can sit and ponder how horrible our land’s history can be. There is a beautiful sculpture there made by The British Ironwork Centre. The British Ironwork Centre is just outside of Oswestry on the way towards Shrewsbury and is famous for the incredible Knife Angel sculpture that has toured much of Britain. It is a fantastic day out where you can roam around the gigantic sculpture park (my favourite is Bumblebee from The Transformers!) and check out the cafe and indoor showroom where you can browse and buy to your hearts content! I highly recommend a visit once lockdown restrictions are lifted.

Sculpture of the eagle with Oswald’s arm at the site of Oswald’s Well on Maserfield

Our first leg took us past the Oswestry Cemetery out towards Morda along part of the Wat’s Dyke path. We passed many fields and areas that I’d never known existed, including Penylan Mill. I could have spent a lot more time exploring this area deeper and is somewhere I will definitely go back to, but Callum stops for no-one and on we continued. The trail leads you out to the back of Oswestry Rural and the Llanforda estate and woods, which despite being only a 5 minute walk from my mama’s house, she only discovered due to lockdown. We have since had many a walk and picnic here. There are some positives to this horrible Pandemic experience! The ruined garden walls of Llanforda Hall are all that remain of the Williams-Wynn family home which burnt down in 1780. Nature has decided to take back the land and trees now grow straight out of the wall brickwork. I recommend visiting in Spring/Summer when nature is in full bloom as it is a truly beautiful, serene and secluded area. See if you can find the memorial that has been set up for a local man that used to enjoy escaping to these woods!

Just after this Callum and I got a bit lost (and not for the first time!) Ive learnt through experience that men don’t seem to be too great at map reading despite wanting to take the lead, and have often gotten lost thanks to following their lead. Having been my mother’s professional map reader before Sat Navs existed, I do tend to do better, but I let Callum continue because, as the great Erol Ozan says “some beautiful paths can’t be discovered without getting lost” and we sure did find some beautiful paths!

On track!

We ended up on the Offa’s Dyke national trail which passes through the Oswestry woods. This is another trail I would like to do more of, but would definitely have to be done in sections as it is 177 miles long along the English/Welsh border from Chepstow to Prestatyn. We may have naughtily crossed the border without realising, breaking lockdown rules, but were not apprehended by the police so were able to continue on our mission to complete the trail. The Dyke is thought to be an ancient defensive earthwork ordered to be built by Saxon King Offa of Mercia in the 8th century to divide his kingdom from the neighbouring rival kingdoms that is now Wales.

The spectacular Candy woods

This path leads you through Candy Wood and the Old Oswestry Racecourse, an 18th century racecourse with the figure of 8 track still visible and used as much of the walking route. The infamous John “Mad Jack” Mytton was among some of the local figures involved in the racing. The racing brought large crowds and money to the area until September 1848 when the last race was held coinciding with the opening of the Shrewsbury-Chester railway line. Part of the grandstand is still visible lying in ruins however the ‘Janus Horse’, a double headed horse sculpture that looks both to England and Wales, remains intact and is a great spot for a photo. This was my favourite part of the trail; I felt lost in the wilderness. This section also has some of the best views over Oswestry and into Wales at 305m in altitude. The racecourse has frequently had snow this winter, providing the most magical winter wonderland scenes that I’ve been lucky enough to enjoy with my family.

On we continued on our walk, with me feeling a bit like a hobbit trying to keep up with Gandalf. We got lost several times over the hours and had to trek through fields of mud where Callum nearly lost his boot, squeeze through bushes that tore our coats and faces to shreds and navigate through fields of livestock.

Sinking in mud!

We had some incredible encounters including 2 massive buzzards flying very close to us calling to each other whilst hunting and we made friends with plenty of cows and horses along the way. The trail led us onto Brogyntyn Park, where Castell Brogyntyn ringwork fortifications and a tunnel remain from the late Anglo-Saxon period in the late 12th century.

The final leg took us to ‘Old Oswestry’, one of Britain’s most impressive Iron Age hill forts dating back to 800BC. Old Oswestry Hillfort is reputed as “The Stonehenge of the Iron Age Period” and remains one of the best preserved hill forts in the UK, according to English Heritage. You can add a walk up and around the hillfort to the trail, however by this stage I was dreaming of my bed and we chose to continue on home. I have however walked around the hillfort many times in the past. It provides stunning panoramic views across North Wales, Cheshire and Shropshire and is a great place to learn about its history with plaques explaining this around the site. The hill fort, known as Caer Ogyrfan after King Arthur’s father in law, is said to be the birthplace of his Queen Guinevere. It is also believed to have been the site for the final battle of the Powys king Cynddylan, the last descendant of King Arthur to rule in Shropshire.

On we trudged back into Oswestry having completed Oswald’s trail. The trail by not means has to be done in 1 sitting, it can be broken down into 5 separate trails and done in stages or you can decide to complete it as you wish. For more information on the trail and maps see

We completed the trail in just over 4 hours without any breaks, which considering we were up and down hills was pretty quick thanks to Callum’s long legs. Callum left me back at my car looking worse for wear. He seemed to skip away still full of energy whilst I took a good 20 minutes sat in my car to regain my strength in order to drive 2 minutes up the road to my mother’s home.

I find walking in nature such a healing experience. I have struggled with significant anxiety and feeling really down during this horrible Pandemic and walking in nature has always helped to alleviate those feelings, particularly in the Shropshire Hills. The Welsh mountain ponies on the Long Mynd always put a smile on my face. Walking the Oswald’s trail plus the therapy session I had with Callum whilst we walked left me feeling calm and renewed despite my physical exhaustion and I slept like a log that night! Thank you Mother Nature and Callum!

Me 🙂

Other posts by Janire:

Semana Grande! The biggest and best festival in the north of Spain.

Yoga and Activity Retreat, Marrakesh with Emma Kelly.

Shropshire Hills for my top 5 hills to hike in Shropshire.

Bonnie Scotland an epic wild camping road trip around the Scottish Highlands.

9 Comments Add yours

  1. Tegan says:

    This was such an informative and fascinating post to read! Thank you so much for sharing! I would love to visit the area, it sounds like everything I love– history, outdoors adventures, beautiful nature… Wow!

    Liked by 1 person

    1. Janire says:

      Thanks so much Tegan! I’m glad you enjoyed it! Feel very lucky to have such lovely places to explore during lockdown right on my doorstep!


  2. bookitletsgo says:

    Thank you for sharing this sounds like a great adventure!

    Liked by 1 person

    1. Janire says:

      Thanks for reading! Glad you enjoyed it!


  3. nina2813 says:

    Wow a 19 mile trek with a detour is LONG! The longest I’ve done is 20 km with some getting lost in New Zealand. I love all the info here. I feel like I could do it myself (until I remember the length)

    Liked by 1 person

    1. Janire says:

      Haha I was shattered by the end of it but it was fun! Ooo I wouldn’t mind getting lost on some trails in New Zealand!!


  4. Bryan says:

    While you were lost, were you a little worried? Or were you confident you would eventually find your way back? Regardless, it sounds like you made some great discoveries along the way!

    Liked by 1 person

    1. Janire says:

      No I was fine! I often get lost but always find my way back on track somehow! Even if it’s an extra few miles walk haha! It was a lovely walk! Glad you enjoyed reading it!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s