The best family-friendly hikes and walks around Winterbourne Steepleton

The parish church is pretty much the only thing left of the Benedictine abbey. It is beautifully preserved and well-maintained.

Not much is really left of the old Benedictine abbey. Remaining building parts are used commercially today. The parish church is still beautifully preserved.

Great place to rest and take in the views

Under the full moon’s silver glow, the Hampton Stones near Abbotsbury do not remain cold, silent granite. As the light reaches its peak, the boulders groan and stretch, shedding their stony shells. They emerge as towering, grey-skinned humans and prowling, heavy-limbed beasts, driven by an eternal, agonizing thirst. They wander the ridgeway, desperate to reach the cool waters of the Fleet. Yet, they are cursed; as the moon begins to fade and the first hint of dawn touches the sky, their forms stiffen. Fearful, they scramble toward their original positions, desperately trying to return to the safety of the earth. But if the moon fades too quickly, they are caught in the open—frozen mid-stride, trapped forever in stone, waiting for the next full moon to grant them another fleeting, thirsty night of life.

When you look out over Abbotsbury, the rolling hills present a striking landscape shaped by thousands of years of human hands. Instead of smooth, uniform hills, the slopes are dramatically stepped and contoured, telling the story of ancient and medieval survival. The Rolling Hills View The chalk and limestone hills of the South Dorset Ridgeway drop sharply into the Abbotsbury Vale. This creates a dramatic contrast: steep, stark ridges covered in wild gorse and grass that soften into a green, undulating basin before meeting the sea. The landscape is a quilt of ancient hedgerows, steep valleys, and dramatic mounds, the most prominent being Chapel Hill, which rises like a small wave right on the edge of the village.

Standing at the crest of the South Dorset Ridgeway gives you one of the most striking coastal panoramas in the UK. Because the ridge rises sharply just inland from the coast, the landscape unfolds below you like a massive, living map. The Fleet Lagoon and Chesil Beach The most dominating feature from this height is the massive sweep of Chesil Beach, a 18-mile barrier of shingles stretching out toward the Isle of Portland in the distance. Trapped right behind it is The Fleet, a shallow, glassy lagoon. From the Ridgeway, you get a clear view of how this narrow strip of water mirrors the sky, contrasting sharply with the rougher English Channel waves breaking on the outer side of the bank. Abbotsbury Vale Looking directly down into the valley, the village of Abbotsbury looks nestled into the rolling green landscape. St Catherine’s Chapel: The 14th-century stone chapel sits entirely exposed on its own smaller hill down in the vale, looking like a tiny solitary sentinel against the backdrop of the sea. The Subtropical Gardens and Swannery: You can trace the dark, wooded canopy of the gardens and the open waterways of the swannery where the Fleet tapers off into the land. On a clear day, the perspective is incredible—you can track the entire curve of the Jurassic Coast all the way out to the red cliffs of Devon in the west.

Legend says the Devil was hanging out up on Portland Hills, feeling competitive. He spotted the church tower down in Abbotsbury and decided to try his luck at a game of quoits, using a massive, multi-ton boulder as his ring. He hurled the rock across the landscape, but his aim was off—it smashed down onto Black Down ridge instead. Today, locals call that ancient burial chamber the Hell Stone, marking the Devil's bad throw.

Great place for free parking if you get here early enough