An easy hour’s drive from Winchester, Shaftesbury is a lovely little town nestled within the rolling hills of Dorset. To reach Shaftesbury, you have the pleasure of driving through the Cranborne Chase Area of Outstanding Natural Beauty, and it’s easy to understand why Dorset-dweller, Thomas Hardy, was so inspired by this area.

Shaftesbury is a small town, with a population of around 6,600. It is also one of England’s oldest towns, with records placing it back to the 8th century and King Alfred the Great. But, what firmly placed Shaftesbury on the modern map is the Hovis advert in the 1970’s, which features a young boy pushing a bike and basket of bread up Gold Hill, before free-wheeling back down its cobbles to the words “get that wheatgerm inside of you boy, and you’ll be pedalling up that hill as fast as you pedal down it“, that has since seen the town’s tourism flourish.

Where to Park:

The most important factor in any day trip. Parking. We parked in the town centre, at Bell Street Car Park. Other options include Angel Lane Car Park and Barton Hill Car Park.

Where to Eat:

Pamplemoose Dorset offers some great takeaway options, like sandwiches and cakes and great coffee. The Mitre Inn is also a lovely pub with terrace views. The Salt Cellar also came highly recommended, particularly for its positioning at the top of Gold Hill itself.

What is there to see and do?

First things first – Gold Hill. A must-see for a visit to Shaftesbury, take a stroll down and back up this beautiful and iconic Dorset landmark. The cottages will make you giddy and the views will have you inspired to traipse across the Blackmore Vale.

Other things: stroll around the quaint town, popping your head into its independent shops and delis. Visit the Shaftesbury Abbey ruins, museum, and gardens. Walk up Castle Hill, a wildlife reserve and hill that gives you views over the town. Walk parts of the Great Wessex Way, a trail stretching from Wiltshire to Dorset, or the Fontmell & Melbury Downs.

Further afield: If you’ve conquered Shaftesbury itself and have some time on your hands, Stourhead (a National Trust site and where Pride & Prejudice was partly filmed) is 20 minutes away, Old Wardour Castle (a castle ruin and English Heritage site) is a mere 10 minutes away. You could also head directly south another 50 minutes to Lulworth and Durdle Door.