“An Astonishing, Achievable Challenge”: Judy Gregory on Walking the Offa’s Dyke Path
Christina·
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Christina·
When Judy Gregory set out to walk the Offa’s Dyke Path, it was more than just a holiday. It was heritage, challenge, curiosity, and somewhere along the way, confidence.
“It was my first long-distance walk,” Judy says. “I’ve never done a long walk before.”
Judy, who was born in Wales but grew up in Australia, decided to tackle one of Britain’s great national trails with her partner, Anne-Maree, over the summer. They spent around three weeks on the trail, walking roughly 15 to 20 km a day, carrying only day packs while their main luggage was transferred for them, by our trusted suppliers. By the time they reached the northern coast, Judy admits it already “felt like such a long time ago,” but the memories are vivid.
Christina sat down for a video call with Judy, now back home in Australia after completing the trail, to chat about why she chose Offa’s Dyke Path, what surprised her most, and the moments she’ll never forget.
For Judy, choosing Offa’s Dyke Path wasn’t random. It was personal.
“I was born in Wales but grew up in Australia, and Monmouth was my grandmother’s shopping town,” she explains. “I’ve always known of the existence of Offa’s Dyke. I’ve seen the signs and heard about it ever since I was a kid.”
Walking the Path also felt like an opportunity to reconnect with place and history.
“I do a bit of work here with Indigenous Australian communities,” she says. “And I’ve noticed some parallels between the experiences of Indigenous Australians and the Welsh people. Offa’s Dyke feels symbolic of that for me, as it was historically built to mark a boundary and separate the Welsh from their neighbours. That’s part of why that path stood out to me.”
There was also timing.
“It felt like a really good time for me to take a longer break,” she says. “It was also a good chance for me to combine this trip, with spending some time in the UK.”
And of course, she smiles: “It also just seemed like a jolly good challenge.”
Judy walked with her partner Anne-Maree, who completed around two-thirds of the route.
“It was certainly good to have somebody to share it with,” Judy says. “I don’t know that I’d want to do something like that completely by myself.”
That said, she did end up walking solo on some days and discovered she enjoyed that too.
“The days where I walked alone, I thoroughly enjoyed,” she admits. “But there’s always this thing of, is it going to be safe or am I going to be lonely?”
For Judy it wasn’t just about who you walk with on the trail, it was also about what happens off the trail. “When you’re traveling alone, it can be lonely in the evenings,” she says. “So it really was good to travel with somebody else.”
“We thought it might be cheating… but it wasn’t”
Judy and Anne-Maree chose a supported itinerary: pre-booked accommodations each night, baggage transfers, and in some sections, a driver to shuttle them back and forth from the trail so they could stay multiple nights in the same place.
Before they set off, Judy wasn’t sure how she felt about that.
“When we were planning it, it felt a little bit as though having a completely organised thing was a bit of a weak way out of it,” she says. “You know, not carrying our own stuff.”
That view didn’t last long.
“It was just such a good way to do it,” she says. “The accommodation was a really big part of what made it a holiday. We had amazing accommodations all along the path and the way that it was all organised for us; I’ve just never done anything like that before.”
At a couple of points they spent three nights in the same place and were transported to and from the trail each day.
“I know when we first booked that I thought, ‘Oh, that’s a bit disappointing,” Judy says. “And actually, it was so nice. You felt a bit settled in a place. I thought we’d feel embarrassed about being driven back to the Path, but it wasn’t like that at all.”
In fact, she says it felt good. “It felt as though we were contributing to the local economy in some way that if we were just camping, we wouldn’t have.”
And for anyone thinking that kind of setup makes it “easy,” Judy is very clear: “Even though it felt like the weak option, it wasn’t. There were days when 15 to 20 kilometres was heaps. You wouldn’t have wanted to go any further.”
Her honest limit?
“If I’m honest, about 15 kms is about enough for me,” she laughs. “I get a bit bored after that if I’m just walking, but everyone is different and that’s what’s great about these trips, there’s something to match every pace and every level of enthusiasm.”
Offa’s Dyke Path might be beautiful, but it is not flat, and Judy didn’t sugarcoat that.
“I always knew I don’t like going down hills,” she says, “and I discovered that that is still very much the case.”
Two descents stand out in her mind.
“The first was going down Hay Bluff. I found that very…,” she pauses, searching for the polite word, “…challenging.”
But the hardest descent of the whole trail wasn’t Hay Bluff. It was a section leading down towards Moel Arthur in the Clwydian Range.
“It’s the hill you come down to the car park for Moel Arthur,” she says. “It’s like it’s not even a Path. I was by myself that day, and coming down there was a really big challenge for me.”
After she made it down, she sat at the bottom and watched someone else attempt the same slope. “I saw him have at least as much trouble as me and that made me feel better,” she laughs.
Weather added its own drama.
“When we were going along Hatterall Ridge, the weather closed in,” she says. “It was very windy and wet, and we’re from Brisbane, so for us, it was so cold, windy and cloudy and we felt like we couldn’t stand up.”
Even though locals might not have called it ‘bad weather,’ Judy explains that for two Australians just a few days into their first long-distance path, “that was a hard one.”
Then there was the heat. Judy & Anne-Maree walked during our heatwaves this summer and although its a climate they’re both used to, it still proved to have its challenges.
“There was one day that was really hard for us,” she says. “It was the day we went through Mellington Hall and on to Montgomery. That was one of the longer days, and it’s very hilly. It wasn’t the hills that got us. I think it was the heat.”
Judy started out carrying around 1.75 litres of water a day, but by the end of that day, she’d already learned one of the trail’s most valuable lessons.
“When we reached Mellington Hall, we’d run out of water,” she says. “I thought the gatehouse there might have a tap or something, but not this time!”
With five kilometres still to go before Montgomery, they decided to take a shortcut along the B road instead.
“I thought, ‘It’s a B road, it’ll be fine.’ It turned out to be busier than expected,” she says. “But we met a lovely local who helped us refill our bottles, that small kindness made all the difference. It was definitely the toughest moment for both me and Anne-Maree, but it taught us a lot.”
Lesson learned? “After that, we carried two and a half litres of water each day and it was just right.”
They also experienced plenty of generosity and warmth from the people who live along the path. “We came across signs offering free water, and even one offering Welsh cakes, though the cool box was empty when we passed!” Judy laughs.
No great adventure is complete without a few surprises and on the Offa’s Dyke Path, even maps and mobile phones can become part of the story!
Navigation on the path:
“For the most part, the wayfinding was excellent,” Judy says. “The signage is really clear, and I had the OS Maps app on my phone anytime I wasn’t sure, I just checked and it showed me exactly where I was.”
There was only one brief moment when she strayed from the route. “I lost the Path a bit in the scree-covered hills after Castell Dinas Brân,” she says. “Maybe for 15 or 20 minutes, and I was probably only 50 metres below the real trail. It was actually quite a peaceful moment, it’s such a beautiful, remote landscape. You can go for hours without seeing anyone, and that solitude makes it feel like you’ve really stepped into another world.”
Even then, Judy found herself smiling. “My phone insisted I was still ‘on’ the path,” she laughs. “Technically, I was, just a little underneath it!”
Moments like these, she says, are part of what makes the trail so special. “There’s a real sense of adventure. The Path gives you just enough challenge to feel like you’ve earned every view and every milestone along the way.”
And finally: Anne-Maree’s moment.
“There was a day when Anne-Maree’s phone pocket-dialled emergency services,” Judy says. “Suddenly her pocket’s saying, ‘What emergency service do you need? Where are you?’ She didn’t even have a SIM card in! We had such a laugh about it afterwards and it shows the system definitely works.”
When asked if there was one single “wow” moment, Judy didn’t hesitate.
“Any time that we climbed a hill and looked back,” she says. “The views across the landscape are just so beautiful.”
She especially remembers how the landscape shifted.
“For us it got greener as we went further north,” she explains. “The south seemed more dry and brown looking. And then suddenly you’re in this heather and these rolling uplands.”
Her favourite landscape of the entire walk?
“I think the Clwydian Range might have been, in terms of beautiful landscape, my most ‘wow, this is incredible,” she says. “You’re up high and it’s all this heather and it was just so beautiful. I loved the way the Path was, you know, rocks placed in it. It was really stunning.”
And there was one emotional milestone: “The very first time I saw the sea in the distance,” Judy says. “I was getting closer to the sea and that was pretty special. You just get this idea of, ‘Oh wow, I really have walked a long way.’ I left the sea and I can see the sea again.”
Offa’s Dyke Path has a reputation for being quieter than some of the UK’s more famous long distance trails, and Judy actually loved that.
“There would be hours where you wouldn’t see anyone,” she says. “When we booked it, we were told that August was a quieter time to walk it, and I loved that it wasn’t too busy.”
Judy and Anne-Maree didn’t bump into many other Australians. “I don’t think I met any Australians,” she laughs. But they did meet “a Dutch couple a few times up around the canals, going over the aqueduct,” and “a walker from London” who kept popping up in the same accommodations.
And then there was social media.
“I was posting every day on the Offa’s Dyke Facebook group,” Judy says. “Around the middle of the trail, in the Knighton area, a number of people recognised me. I’ve never had that before. People on the trail would bump into me and say, ‘Oh, are you Judy? I’ve been following you.’ It was both hilarious and wonderful.”
People always ask about British weather. Judy’s answer: “We actually got really lucky.”
“We had one wet day,” she says. “We were walking through the Wye Valley, through the forest up behind Tintern, and it was quite wet that day.”
That one rainy day taught them something practical.
“We thought the covers on your backpack would keep your backpack dry,” she says, “and they don’t. The rain goes down between your back and the backpack. So we learned we really needed to carry more plastic bags. We wrapped the books and everything after that.”
But aside from that one soaking, Judy and Anne-Maree mostly had heat and blazing sunshine, which is exactly why water became such a big deal.
“I kept thinking, I don’t know if I could do this in the wet,” Judy says. “Because the one day it did rain, we saw how quickly the Path becomes a torrent of water. So I think we were probably better off in the heat and the dry.”
“It’s given me confidence”
Offa’s Dyke Path was Judy’s first-ever long-distance trail. Now that she’s finished it, would she do another?
“Oh, definitely,” she says. “It’s given me confidence that I didn’t have before.”
Judy doesn’t consider herself “a sporty person.” “I work pretty hard to keep fit,” she says, “but I don’t consider myself especially athletic, or resilient or anything.”
Walking Offa’s Dyke Path changed that self-image.
“It’s given me confidence to do that kind of thing,” she says. “I’ve got in my head I’d love to do a long walk every year. I’m not somebody who’s going to go out and do a 10k on a weekend just for the sake of going for a hike. I quite like the idea of it being in a place I’ve never been and that being a holiday.”
Next up: home turf. “We’re going to do a walk in Australia next,” she says. “There’s a walk in Victoria called the Great Ocean Walk. It’s 110 kilometres. We’ve found a similar sort of arrangement where we can do it over 10 days, so it would actually be shorter days than what we just did. You’ve got to get the tides right, because there’s a section where you walk along the beach, so we’re hoping to do that towards the end of next year.”
Would she come back and walk in the UK again? “Yeah, I’d like to do more,” she says though she’s honest about the reality. “It is a really big deal to get over there. I managed to spend three months in the UK this year and that was pretty special. I’m not a great fan of those long haul flights,” she laughs.
Part of that extended stay included time in South Wales, at her grandmother’s old house just outside the little village of Skenfrith (“about halfway between Abergavenny and Ross”). “I lived there for two months this year,” she says. “I’ve never taken time like that off work before. I was doing some writing. It was amazing.”
Writing, in fact, is Judy’s other quiet project.
“I took about 30,000 words of notes and about 1,300 photos,” Judy says. “I was taking photos of all the interpretation signs and everything just to remind me. I would really like to write a novel of somebody walking the Path. Not about me walking it, a novel. It’s kind of the next project in line.”
At the end of our chat, I asked Judy to sum up Offa’s Dyke Path in just three words.
She laughed. “I had trouble with this,” she admitted. Then she said:
“An astonishing, achievable challenge.”
Why those words?
“Because it’s both incredible,” she says, “but it’s also achievable. You just have to put one foot in front of the other and it’s really not that hard. And that surprises me.”
Her advice to anyone thinking about it?
“Carry more water than you think. Respect the downhills. Put your guidebook in a plastic bag. Take the ‘weak option’ it’s not weak, at all, and remember: you’re allowed to surprise yourself.”
“It doesn’t take long to recover,” Judy says. “Even on the days you think you can’t, you can.”
Judy’s journey is a wonderful reminder of the joy, challenge and connection that come with walking a long-distance trail. If her story has inspired you to experience the magic of the Offa’s Dyke Path for yourself, you can explore our range of Offa’s Dyke itineraries here.
