Perched high on a hilltop with sweeping views of the Blackmore Vale, Shaftesbury offers postcard-perfect Dorset charm paired with deep-rooted history. Just a few miles down the road, Gillingham delivers a quieter, rural counterpoint — a practical base for exploration with strong cultural and historical ties of its own.
Together, these two North Dorset towns invite slow-paced visits steeped in heritage, greenery, and proper countryside character. Whether you’re on a gentle weekend break or planning a longer trip, Shaftesbury and Gillingham promise peaceful landscapes, market-town traditions, and some of the best views in the county.
Shaftesbury is one of the oldest and highest towns in England, and its skyline reveals a rich medieval past. Start with Gold Hill — a steep, cobbled street famously featured in the 1973 Hovis bread advert — which remains one of Britain’s most iconic images of rural life. At the top enjoy panoramic vistas from Park Walk, a peaceful promenade lined with benches and flower beds.
Nearby, the Gold Hill Museum sits within historic 17th-century buildings. Inside, you’ll find exhibits on rural life and traditional farming tools used in the area, along with stories that reflect the town’s long history.
Just a short walk away, Shaftesbury Abbey Museum and Gardens tell the story of a once-powerful Benedictine abbey founded by King Alfred. Today, visitors can explore tranquil gardens, browse interactive displays, and listen to audio experiences that share the lives of those who once lived and worshipped there.
Gillingham may not sit high on a hill, but it holds its own historical and cultural appeal. As Dorset’s most northerly town, it borders both Somerset and Wiltshire and is the only town in North Dorset with a mainline train station — making it a useful base for exploring further afield.
Historically a Saxon settlement, Gillingham developed rapidly in the Victorian era thanks to the railway and local industry. Its fascinating story is told in Gillingham Museum, which offers a detailed journey from prehistory through Tudor education to the present day.
Of particular note are its connections with artist John Constable, who painted several local landscapes in the 1820s — some of which you can still visit today.
Those who enjoy walking in nature will find plenty to appreciate here. Just outside Shaftesbury, Duncliffe Wood offers peaceful trails through ancient trees. Managed by the Woodland Trust, it’s especially lovely in spring, when bluebells fill the ground beneath the canopy.
The North Dorset Trailway runs along a former railway line, offering a scenic route through fields and quiet villages for both walkers and cyclists.
Just across the county line in Wiltshire, the National Trust site at Stourhead features landscaped gardens, water features, and classical-style temples making it ideal for a relaxing day outdoors.
Shaftesbury and its surrounds make the most of Dorset’s rich produce. At the top of Gold Hill, The Salt Cellar Café offers coffee with arguably the best view in the county. Down in the town centre, The Grosvenor Arms serves contemporary British dishes in stylish surroundings, while La Fleur de Lys is a long-standing favourite for a more intimate dining experience.
Out in the surrounding countryside, Udder Farm Shop is a local go-to for fresh produce, homemade meals, and a café with views over the Blackmore Vale.
Regional cheeses, local ales, and treats from Shaftesbury’s regular farmers’ markets are all part of the experience. These markets are great for finding homemade chutneys, fresh bread, and other local specialities.
Shaftesbury’s annual Snowdrop Festival brightens up February with thousands of blooms planted around the town. In spring, the Food & Drink Festival (also known as ‘Feastival’) takes over the streets with stalls, tastings, and community spirit.
Come summer, the Gillingham & Shaftesbury Show bring the crowds with vintage tractors, local crafts, livestock competitions, and live entertainment.
Shaftesbury and Gillingham are more than pretty scenes, they reflect Dorset’s countryside at its most welcoming and characterful.
Whether you’re browsing small shops, wandering through peaceful woods, or sitting down with a slice of cake overlooking the rooftops, these towns invite you to slow down and enjoy the moment.
Start planning your visit and see for yourself what makes this corner of Dorset so special.