Day trip : Shaftesbury

Gold Hill, Shaftesbury

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.

Top 5 Cotswolds villages within 1.5 hours of Winchester

Drink, Food, Shopping, Travel

The picture-perfect Cotswolds is a firm favourite in our household. It’s just close enough for a day trip, or an easy weekend away, and even in bad weather it’s still utterly charming.

Although it feels like a bit of a trek, the nearest stretches of the Cotswolds are just over an hour away from Winchester (and even closer if you’re based in north Hampshire). Pootle up the A34/M4 and you’ll hit Cirencester (the “Capital” of the Cotswolds) in an hour and fifteen.

So if you fancy a beautiful day trip for some stunning scenery and sublime pub lunches, jump in your car and try these villages.

1. Castle Combe

When I think of the Cotswolds, I think of Castle Combe. The beautiful sandstone cottages, sweeping streets, and the tranquil river running by are just exquisite.

Castle Combe is proclaimed as one of England’s prettiest villages, as well as rising to fame through being a film location for some big tv/film hits, most notably Steven Spielberg’s War Horse, Downton Abbey, and Stardust.

The White Hart pub serves a great range of easy pub classics, including jacket potatoes, stews, sandwiches and pies. If you’re after something special, The Manor House Hotel has become a firm Insta-favourite for its sweeping, ivy-covered façade, or otherwise try The Castle Inn (opposite the White Hart) which is the sister Inn to The Manor House Hotel.

And for any Harry Potter fans, nip over to neighbouring village, Lacock, to visit Hogwarts, the home where Professor Slughorn pretends to be an armchair, and one of the Godric’s Hollow filming locations.

2. Bibury

Another contender for “prettiest village in England”, much of Bibury is protected by The National Trust, and for good reason. Arlington Row, which is the most photographed row of cottages in Bibury, dates back to the 1300’s, and you can even stay in one of them.

Grab a bite to eat at The Swan Hotel, which sits on the River Coln and is another Cotswolds Insta-landmark, again for its ivy-covered façade.

3. Poulton & Meysey Hampton

Ok, so whilst these are technically juuust outside of the Cotswolds, they’re both right on the edge and so sweet that they deserve a spot on this list. I’ve grouped them together because they’re a stones throw from each other and an easy walk between. Lunch at the Masons Arms, which sits on Meysey Hampton’s beautiful green, surrounded by Cotswold cottages. The green even has the old horse mount steps from time-gone-by that you can walk up.

4. Biddestone & Slaughterford

Just a 35-minute cross-country walk between each other, Biddestone and Slaughterford sit just across the Cotswolds border, and both are equally charming in aesthetic.

Biddestone’s White Horse pub is well regarded, or why not try The White Hart in Ford, and walk in a loop between Biddestone, Slaughterford and Ford.

5. Burford

Slightly larger than the previous 4 places, Burford boasts a much larger food scene and a small high street to boot. If you like antiques and homeware, Burford is the one for you.

Walk along the River Windrush towards Swinbrook on this scenic 6.5km walk before circling back to Burford for a well-earned pub lunch.