Easy hikes and walks around Oborne

Sherborne Castle & Gardens, often called the "New Castle," was built by Sir Walter Raleigh in 1594 after he decided the neighboring 12th-century ruins were a bit too "medieval chic" for his tastes. Today, it remains the private home of the Wingfield Digby family but is open to those who want to see how the other half lived during the Tudor and Georgian eras. ​The Castle Interior ​The house is a grand H-shaped mansion that has managed to hoard four centuries of high-end decor. It’s essentially a very large, very expensive time capsule. ​The State Rooms: Features a blend of Tudor architecture and 18th-century "upgrades," including ornate white marble fireplaces and Georgian sash windows. ​Art & Porcelain: The walls are lined with nationally important collections of fine art and furniture that make a modern IKEA catalog look deeply upsetting. ​The Family Museum: Located in the cellars, this museum covers the castle’s "Great Stories," including Raleigh’s local legacy and the 1753 transformation of the grounds.

Sherborne is so fancy it has "spare" castles. Sherborne Old Castle started as a 12th-century fortified palace for a bishop who clearly valued "defense" over "patience." Fast forward to 1592, and Sir Walter Raleigh moves in. He tried to modernize the drafty ruins but eventually gave up, presumably after realizing medieval plumbing is just a hole in a wall. ​He built Sherborne New Castle nearby—a chic Elizabethan mansion. During the Civil War, Parliament got annoyed and "slighted" (read: blew up) the Old Castle. Now, the ruins serve as a romantic backdrop for the New Castle’s "Capability" Brown gardens.

The Pageant Gardens bandstand is the spiritual home of "aggressively pleasant" afternoons. Built to commemorate the 1905 Sherborne Pageant—a massive theatrical flex involving 900 locals in tights—this octagonal masterpiece is where brass bands go to battle the sound of falling leaves. ​It’s the ultimate Victorian stage for looking dignified while holding a tuba. Surrounded by pristine lawns and flowerbeds that would make a perfectionist weep, the bandstand serves as a reminder that nothing says "British Summer" like listening to The Liberty Bell while your ice cream melts at a record-breaking 18^\circ\text{C}. Pure, unadulterated whimsy.

If you think your homeowner’s association is strict, try the Almshouse of St. John the Baptist. Established in 1437, it was basically a 15th-century "assisted living" facility for the "brave and the broke." ​The rules? Absolutely medieval. You had to be "of good character," which in 1437 mostly meant "doesn’t throw mud at the Abbot." The jewel inside is the Sherborne Missal, a book so fancy it makes your iPad look like a rock. Today, it stands as a gorgeous Hamstone time capsule where history is thick, the chapel is tiny, and the vibes are strictly "pious chic."

Founded in 1550 by King Edward VI, Sherborne School is an elite boys' independent school that practically owns the town’s aesthetic. Built atop the site of a former Benedictine priory, its honey-colored Hamstone buildings blend seamlessly with the adjacent Abbey. ​It is a "Harry Potter" fever dream of cloisters and tradition, but its real prestige lies in its alumni. This is where Alan Turing solved puzzles before Enigma and where actors like Jeremy Irons and Hugh Bonneville learned their craft. It remains one of the UK’s architectural and academic heavyweights, turning out "Old Shirburnians" for nearly five centuries.

Originally a Saxon cathedral, Sherborne Abbey is a golden-stoned masterpiece of Perpendicular Gothic architecture. Its claim to fame is the fan vaulting—arguably the earliest and most spectacular in England—which spreads across the ceiling like delicate stone lace. ​The Abbey has survived fires (started by a bickering abbot and townspeople in 1437), the Dissolution of the Monasteries, and the test of time. Inside, you’ll find the tombs of West Saxon kings and the stunning Great West Window. It remains a living "lantern" of Dorset, glowing with honey-colored Hamstone and a quiet, ancient majesty that defines the town.

I always make time to pop in on my walks in this area as it is wonderfully calming and peaceful. I like to just sit and marvel at the talent of the architecture.

Sandford Orcas sits beneath Holway Hill, where the summit stands at 172m. The village itself is full of English history, with the Manor house built around 1550 AD and the church of Saint Nicholas thought to be from the 13th century. Surrounded by the Dorset countryside, it is a beautiful place to explore and to embrace its distinctive characteristics.