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  • Writer's pictureSasha C

Spending 24 Hours in Dorset’s Prettiest Town, Shaftesbury

Updated: Oct 15, 2022

Perched on a hill overlooking the rolling hills of Dorset is Shaftesbury, the historic market town. When you think of the cute and quaint, quintessential countryside town, Shaftesbury is it. It’s got everything – your cobblestone streets, views and greenery, thatched cottages, lovely cafes and shops, B&Bs. It was founded over a thousand years ago and is truly untouched. The town makes an excellent day trip on its own and can also be a great stop while exploring the Jurassic Coast or Cranborne Chase AONB.

We visited Shaftesbury this summer by chance really – friends were getting married in the area (an ideal setting!) and we jumped at the opportunity to stay near what’s regularly called the UK’s prettiest town!

We hopped on a train out of London the day before the wedding to explore and round up our top tips on how to spend 24 hours in Shaftesbury, Dorset.

A view of Shaftesbury High Street and St Peter's Church
Shaftesbury is home to a lovely high street

Start off with a coffee

Shaftesbury has plenty of options for breakfast – whether you’re looking for a quick coffee and pastry at Coffee No.1 or a filling breakfast at The Salt Cellar or The John Peel. The area is also home to many quaint B&Bs so it’s likely that you’ll have ready-made access to a tasty breakfast.

Wander Shaftesbury Abbey and Park Walk

Founded originally in 888 AD by King Alfred, Shaftesbury Abbey was once England’s foremost Benedictine nunnery before the destruction ordered by King Henry VIII. Now just the foundations of the abbey remain. The museum and gardens are free to explore. Just outside the abbey is Park Walk, known for its reaching views over St James and across the expansive Blackmore Vale.

Time for lunch

Right on the High Street, is the independent Shaftesbury Deli. Sourcing mainly from local producers, you can choose from a range of fresh sandwiches, savoury pies, as well as cakes to take away for a picnic. If you fancy staying a bit longer, Shaftesbury Deli also has a cosy tea room for the ideal afternoon break.

Ecco Gelato in Shaftesbury, Dorset
The best gelato in the UK!

Explore the local shops

Shaftesbury is full of lovely independent shops catering to a wide range of interests. Shaftesbury Wine is a foodie haven with a wide selection of wines (of course) and Bright Blooms is a perfect for those with a green thumb. Just before exploring the iconic Gold Hill, pop into Ecco Gelato, a bright and friendly shop with deliciously creamy gelato or The Folde, an earthy homeware and gift shop.

The famous cobbled Gold Hill on a sunny day with Blackmore Vale in view
Introducing the UK's most romantic street, Gold Street

A trip to Gold Hill

The steep cobbled street is famous for its picturesque appearance – historic cottages line the stone streets before the incredible view. Gold Hill has two claims to fame – regularly described as one of the most romantic sites in England AND the 1973 ‘Boy on a Bike’ Hovis Bread commercial that’s been voted Britain’s favourite advert of all time.

End the day in the pub

The Mitre is an excellent classic pub, with a great menu and super friendly staff. If the tasty pies and fish and chips weren’t enough, the back decking has sensational views over Blackmore Vale. Book Table 26 for the perfect setting.

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