Picture perfect Shaftesbury lies on the edge of Cranborne Chase, a designated AONB (Area of Oustanding Natural Beauty) in Southern England. I’d seen lots of photos of Shaftesbury online and knew it was packed with beautiful streets and interesting history, but also knew it was quite small and would need tying in with somewhere else to make a break of it. We chose neighbouring Cranborne Chase, to give us a balance of picturesque towns, history and English countryside. This is a much lesser known and visited part of England so was very quiet, and I’m excited to share with you.
You could choose to stay in Shaftesbury itself, or choose one of the area’s many ‘pubs with rooms’ such as The Beckford Arms or The Royal Oak, which make a perfect base out in the countryside for walks, eating and wine drinking without the hustle and bustle of a town centre.
Day 1 – Shaftesbury and The Wardours
We arrived early in Shaftesbury to ensure a car parking space as there is only really one, quite small, central car park. Shaftesbury is the only hilltop settlement in Dorset which means it commands lovely views out over the countryside and is made up of some beautiful steep hills. There are a few sites worth visiting, so spend your first morning exploring Shaftesbury itself.
A. Gold Hill
Start at the most famous point and get some photos before the crowds arrive. Gold Hill (famous for being Hovis Hill, from the bread adverts) is one of the most recognisable streets in England, its beautiful cobbles and rickety houses being picture perfect England. From the top of the hill you can see the rolling fields in the background, although on the day we visited it was a bit misty. It’s actually the 5th steepest street in England, so be prepared to get a bit puffed out walking back up it!



B. Gold Hill Museum
The Gold Hill Museum is deceptively big. Opening at 10.30am, it’s worth popping in to learn a bit more about the history of Shaftesbury including its Medieval history, to becoming a lace and button trading town, to modern times. The Museum also has a nice little garden with more nice views to take in.
C. Shaftesbury Abbey
Shaftesbury Abbey was founded in the 800s by Alfred the Great, the most famous Anglo Saxon King. He believed in education for both men and women, and set up the Abbey as a place of learning and retreat – he put his daughter in charge as the Abbess. Over the years, the Abbey welcomed many wealthy visitors including King Cnut who died here. Katherine of Aragon also visited on her way to London to marry Henry VIII.
Ironically it was then Henry VIII who then destroyed the Abbey during the dissolution of the monasteries in 1539. All that remains today is some of the foundations, a beautifully done garden and a great museum which tells the history of the Abbey.

After the morning in Shaftesbury, it’s then time to head out in to the countryside. There are various options for lovely walks in the area but I’m a sucker for a Castle so decided to head 20 minutes down the road into Cranborne Chase to Old Wardour Castle and do a walk from there.
D. Old Wardour Castle
Old Wardour Castle was such a treat – I didn’t know what to expect but it blew me away. This Castle was built in the 1380s as a fortified manor home, rather than a Castle as we often know them. In the 1500s it was updated in to Elizabethan style and then, in a Civil War siege of 1644, the owner accidentally blew up one side of his own castle, while recapturing it from the Parliamentary army. From there, the Castle was then never repaired as the family built New Wardour Castle just a short distance away as a stately home, and turned Old Wardour into a picturesque park of ruins, lake and woodland. It remains like this today.
E. Wessex Way walk
After visiting the Castle, finish a day off with a walk which takes you on a loop through rolling fields and woodland between Old and New Wardour Castles, all within Cranborne Chase AONB. The route takes around 1.5 hours and is 3.5 miles long. The route we followed can be found HERE. As you can see we got totally rained on during this walk, but as they say – there’s no such thing as bad weather, only a bad choice of clothing -including mine, when I got wet feet.

Day 2 – Fonthill Estate (or alternative Cranborne Chase walk)
Day 2 is all about a nice long walk in the countryside. There are a huge array of Cranborne Chase walks to do and their website is great with various options detailed, ranging from easy to hard. We hose a medium walk, detailed HERE. The walk was 7 miles and took us around 4 hours to complete, with lots of photo stops.
As you can see, the good old English weather did a massive U-turn and went from cold, miserable rain the day before to glorious, boiling sunshine in the course of 24 hours. At least I didn’t have wet feet again.
A. Beckford Arms to Berwick St Leonard
We started at The Beckford Arms and walked from there through rolling countryside, woodland and some picturesque small hamlets to reach Berwick St Leonard. In Berwick, there is a lovely church which is now unused, apart from one service a year. I find it sad that churches like this are slowly disappearing all over the country, but also understand it’s a sign of the times and not every small village can keep a church going anymore. I hope we manage to preserve many though, as the buildings really are historic and special.

B. Berwick St Leonard to Ridge
After visiting the church, head across the field full of sheep until you reach Fonthill Bishop, and then walk along the public Bridleway until Ridge. The path here is clearly marked and there are some beautiful rolling landscape views.

C. Ridge to Beckford Arms
The final stretch of the walk brings you back across to The Beckford Arms, through some clover fields and varied woodlands. The highlight of this part of the walk though is Fonthill Lake which you can divert to stroll around if you want to see more of it.

After a couple of long walks in the last 2 days, you’ll be ready to collapse with a glass of wine, so spend your final evening resting, relaxing, drinking and eating before heading home.
I hope you’ve enjoyed my little tour of this wonderful lesser known piece of England. What do you think of it? Stay safe and happy travelling everyone.
Absolutely gorgeous photos! Seems quite peaceful as if you had every corner just to yourself. Indeed, even the pub seems deserted. Glad your luck with the weather changed.
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It was definitely pretty quiet and well off the tourist track which was really nice 🙂 And yes, typical English weather!
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Beautiful pictures! I just love your posts on these towns that are the unsung beauties of England and all they offer. They confirm the idea that I could live there and I show them to the husband trying to convince him that he could live there too 🙂
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Oh I’m so glad you enjoy them Meg 🙂 It’s for sure a beautiful place to live and so many lovely homes to choose from. BUT they do require a lot of maintenance. Worth it though, in my humble opinion!
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I forgot to say….Happy happy Thanksgiving 🙂
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Thank you so much! Happy Thanksgiving to you too 🙂
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So beautiful Hannah, I’ve not visited Shaftesbury but seen photos of its famous hill many times. The surrounding area looks beautiful and totally unspoilt and I’m sure you had a lovely time despite getting your feet a bit wet!
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So glad you like it Marion and thanks for reading. It really was a completely unspoilt area which was perfect for walking. The wet feet didn’t matter at all 🙂
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Gorgeous photo’s! I had no idea Gold Hill was the Hovis hill. I had it in mind that it was in Yorkshire somewhere. I’m not far from tge Wardours, I actually walk the dog at Old Wardour sometimes. I can revisit the area now with some fresh ideas, thank you for the inspiration 😊
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Thanks Helen and thanks for reading! Yes I thought the same – it’s because the advert is set in Yorkshire so you automatically think it’s there! Oh wow you’re really close so that’s amazing to show you some ideas close by 🙂 Have a nice evening
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Certainly looks like a lovely area to explore! Your pictures are gorgeous…love the pretty houses!
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Thanks so much Linda, it really is a lovely area to explore, perfect for a ‘taking it slow’ relaxing weekend 🙂 Thanks for reading and have a nice evening
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Gorgeous as always! At first glance, I’d believed Shaftesbury to be part of the Cotswolds, as the cottages along cobblestone streets seem to resemble those in that particular region. In any case, it looks to be delight going from cottage to abbey to castle offers a bit of everything to enjoy for a weekend getaway!
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Thanks Rebecca! Yes it definitely looks a bit like the Cotswolds for sure, and it’s only around 30-45 minutes drive away so is quite close. It’s a great spot for a weekend away. Thank you so much for reading – have a great evening 🙂
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And I forgot to say…Happy Thanksgiving 🙂
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Thanks, Han! Have a wonderful upcoming weekend. 🙂
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Absolutely beautiful! There are so many interesting and scenic spots in England I would like to explore some time. Thank you for your advice.
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Thank you so much! Yes it’s a bit like Germany really, get a bit off the tourist path and there are so many lesser known areas to discover 🙂 Thanks for reading.
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So many great things to do and see here! English countryside to the max. That street looks really steep in the photo. I imagine it feels a lot steeper in person.
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Definitely English countryside to the max, it was such a restful visit. The hill is really steep….it was used in a commercial for bread here for decades where a boy whizzed up on his bike holding loaves of bread. And then there is a comedy sketch about it which is really famous in England where a comedian walks up the hill and it takes him so long because it’s so steep…..basically saying the commercial is a load of rubbish. Thanks for reading, hope you’re having a wonderful Thanksgiving 🙂
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It almost seems you were the only ones there (well, you and the sheep 😉). I’m a sucker for a castle as well (and we don’t have them here in SA), so I always enjoy your posts where there is a castle! And what a lovely walk on the second day – pretty houses and green fields and then ending the day in that beautiful pub … sounds perfect to me!
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Totally just us and the sheep – we barely saw anyone else on our walk…well other than the public footpath took us through someone’s garden as they were hanging the washing haha! Castles are wonderful, we are so blessed with them here in England. So glad you enjoy the posts, and thanks for reading 🙂
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Absolutely beautiful!! I’d spend so much time taking pictures of the idyllic houses, they’re so cute!
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Aww so glad you think so Lyssy – and yes you would definitely be snapping away 🙂 Happy Thanksgiving, hope you’re having the best day
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Thank you!! 🥰
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What a pretty countryside. I’d love to live or even stay in one of the Gold Hill houses. Maggie
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Thanks Maggie, and you can actually rent one of the houses on Gold Hill I think as it’s an AirB&B now!!! Thank you so much for reading 🙂
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Such a great outing Hannah.and beautiful surrounding area .Love your photos..
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Thanks so much for reading Anita, and really glad you like the photos 🙂
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Hannah…what a gorgeous countryside tour!!
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Thank you so much, really glad you enjoyed it
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What a beautiful area and that castle/stately home is cool. Imagine having enough money that you go, “Repair? Nah, just leave it and we’ll build another.” 🙂
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Thank you so much for reading, it was a really lovely area. Haha, can you imagine…nah I’m bored of that castle anyway, let’s just build another one
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In my next life…
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The cobblestoned streets lined with all those houses that look like cute cottages in Gold Hill looks so charming. Oh wow does that seem like a cardio workout though. Agreed, it’s always good to get to the best viewpoints early before the crowds appear. The Old Wardour Castle looks pretty amazing and such a neat area to explore and photograph.
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Thanks so much for reading, it really was a lovely and varied place to visit. I agree Gold Hill is a bit of a work out – my legs definitely felt it for a bit afterwards hahaa! Have a lovely Sunday evening.
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Cobblestone roadways, slate shingles and continuity of structures…picture perfect, indeed! Beautiful countryside views, with quite a steep grade. Love the Old Wardour Castle! You certainly have some outstanding, beautiful areas to explore, dear Hannah, and I’m happy that you share your visits. 🙂
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So glad you like it Phil, thanks for your kind words 🙂 Have a wonderful Sunday!
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Very enjoyable! These little villages are wonderful places to walk and explore. I like the idea of pubs with rooms. The old castle ruin has such interesting shapes.
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They’re lovely aren’t they…..and yes, we love a pub with rooms in England – they are like a laid back hotel, although now they are becoming popular we have all the really posh, expensive 5* ones popping up too which I always think lose a bit of the pub charm! Thanks so much for reading Ruth 🙂
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Absolutely wonderful tour and photos, Hannah. You’re far too young to remember the Hovis adverts!!
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It’s such a beautiful area. I just remember my family playing the Ronnie Barker sketch up the hill over and over again – I have no idea why it’s so funny but I can’t help laughing every time 🙂
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Ah – I’d forgotten that; Barker was a comic genius – but the original advert was funny enough! 🙂
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I think this is the best I’ve seen till till now. You’re amazing!
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From gloomy to sunny. What a difference a day makes!
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There may not be a prettier sight in England than the cottages and cobblestones of Gold Hill against the rambling North Dorset countryside. With stunning views over a patchwork of fields and hedgerows, together with a rural charm that is reminiscent of days gone by, Shaftesbury is, nevertheless, a town that has everything you could want for a lovely day out. You really live in such a beautiful part of the world that beckons to be explored. Thanks for sharing and have a good day 🙂 Aiva xx
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It’s just so beautiful isn’t it, I agree it’s definitely one of the most beautiful streets in England. Thanks for reading and you too 🙂 x
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