Top Things to Do in Shaftesbury, Dorset

Top Things to Do in Shaftesbury, Dorset

Home to the view that stole the hearts of the nation, the hillside market town of Shaftesbury in Dorset is all cottages, cobblestones and jaw-dropping panoramas. Steeped in history and steep in nature, the town’s unique position and rich history make for a destination that’s truly one of a kind. 

Long the source of inspiration for poets and playwrights, walkers and wanderers, Shaftesbury has been a thriving settlement since the Saxon times. With a stunning vantage point overlooking Blackmore Vale, the town’s views were forever entrenched in the hearts and minds of the nation after featuring in the famous Hovis advert of 1973, directed by Ridley Scott. 

As well as its picture-perfect vistas, Shaftesbury is also an understandably popular destination for holidays in Dorset in its own right. Wedged between the two coasts of the South West peninsula and surrounded by sprawling countryside, it offers plenty to see and do nearby. To give you the best head-start during your boutique retreat, we have put together the top things to do in Shaftesbury: 

Blackmore Vale

A broad valley flanked by chalk hills and downland, the Blackmore Vale sits between the Cranborne Chase National Landscape (formerly known as AONB) and the Dorset Downs. Banded by the flowing body of the River Stour, it makes for a really photogenic area in which to walk, talk and burn through the calories. For the best vantage points, Hambledon Hill, Melbury Hill, Duncliffe Hill, Melbury Beacon and Castle Hill all provide stunning views over the Vale. 

Castle Hill

The site of a Saxon hillfort, Castle Hill in Shaftesbury is a great choice for local strolls. An important sanctuary for wildlife within walking distance of the town centre, it supports a range of different habitats and species. Keep your eyes peeled for the 130 types of plants and 40 species of birds which have been found here and gaze out over the horizon, seeing as far Glastonbury Tor on a clear day. 

Cranborne Chase National Landscape

To the east of Shaftesbury, the Cranborne Chase Area of Outstanding Natural Beauty is another superb place to explore during your holiday. Especially popular with walkers, its diverse landscapes include chalk grassland and escarpments, ancient woodlands, river valleys and more, offering something and somewhere for everyone within its 380sq miles. The highest point of the National Landscape, Win Green, is only 5 miles from the centre of Shaftesbury and well worth a trip for the panoramas.

Duncliffe Wood 

Duncliffe Wood on the twin summits of Duncliffe Hill is one of the oldest and biggest areas of woodland in North Dorset. Only 2 miles from the town and with plenty of parking available, its waymarked trails are a tempting proposition for year-round strolls. Notable features include the old coppice stools of small-leaved lime trees, believed to be between 600 and 1,000 years old. 

Festivals and Events

To add a fun dimension to your holiday in Shaftesbury, you can time your stay to coincide with one of the brilliant festivals and events that take place in the town throughout the year. Subject to restrictions, you can pencil in the Snow Drop Festival in February, Shaftesbury Food & Drink Festival in May, Gold Hill Fair in July, Shaftesbury Fringe in August and Shaftesbury Carnival in October. 

Gold Hill

No trip to Shaftesbury would be complete without an amble along Gold Hill, made famous by Ridley Scott’s Hovis advert, Boy on a Bike. Voted the nation’s most iconic advert of all the time, the Hovis ad featured a boy pushing a loaf-laden bike up the steep, cobbled street of Gold Hill. Head there today and enjoy the nostalgic feel and the magnificent countryside scenery beyond. For the full experience, you should also pop into Gold Hill Museum and Garden too. 

Kingsettle Wood

Just outside of Shaftesbury, Kingsettle Wood promises a delightful escape sandwiched between leafy canopies and wildflower-peppered floors. Elevated above the town at 239m, it affords stunning glimpses of the town and the surrounding Dorset countryside through the trees. One of the best times of year to visit the woods is in spring when seas of bluebells take over in a flurry of bluey-violet.

Melbury Vale Vineyard 

Only a mile or so south of Shaftesbury is Melbury Vale Vineyard. Setting up shop on a 28-acre, south-facing hillside, the vineyard was founded in 2003 and, along with its onsite winery and shop, provides a great visitor attraction in the area. With a range of delicious grapes and fruit on its sun-kissed slopes, the vineyard produces still and sparkling wines, ciders, liqueurs and brandy – offering unique blends for every occasion.

Old Wardour Castle

In a peaceful lakeside setting near Tisbury, the dog-friendly Old Wardour Castle is around 10 miles from Shaftesbury but well worth the drive for its atmosphere and audio tours. Once one of the most daring and innovative homes of its time, this 14th century castle was built with luxury and lavish entertainment in mind. Despite this, the castle and its varied inhabitants were embroiled in many nasty feuds and wars over the centuries, including a final fatal siege in the 17th century. 

Shaftesbury Abbey Museum & Gardens

Close to Gold Hill, Shaftesbury Abbey boasts unrivalled views across Blackmore Vale. Established by King Alfred the Great in AD888, it was once the country’s most important Benedictine nunnery and played a crucial role in the prosperity of the town for more than 650 years. Today, the abbey’s foundations have been brought back to life through the onsite museum and gardens. 

Shaftesbury Arts Centre

Founded in 1957, Shaftesbury Arts Centre is located in the old covered market on Shaftesbury’s Bell Street and is recognised as being one of the best volunteer-led arts centres in the South West. Among its schedule of events, you can look forward to amateur and professional plays, films, stand-up comedy, creative exhibitions, workshops and more. With something happening most days, its well worth keeping tabs.

Town Walks in Shaftesbury

If you are hoping to familiarise yourself with Shaftesbury a little more, there are many superb town walks. The Park Walk and Shaftesbury Heritage Trail lead you past important buildings in the town and are accompanied by blue plaques which detail information about the town’s history and certain landmarks. If you are following your own route, make sure you see the Gothic Revival town hall, St Peter’s Church, the old cattle market, Holy Trinity Church and St James’ Church.

 Feeling inspired? Take a look at our luxury cottages in Dorset here.

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