The best road cycling routes around Oborne

Paddock Garden is Sherborne’s way of saying, "We’re modern now, but with layers of drama." Opened in 2005 by Alan Titchmarsh (the patron saint of sensible trousers), it’s built on the ruins of 18th-century cottages that were demolished just so the neighbors could have a better view. Rude. ​During WWII, German bombers mistook the girls' school tennis courts for something more threatening, leaving the garden with some unintentional "landscaping." Today, it’s a sustainable flex: the paths are made from half a million recycled plastic straws, proving that Sherborne is both posh and eco-conscious.

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.

A song that – originally from the American gospel tradition – has begun its journey around the world, fits wonderfully with this house of God, which the parish community has entrusted to the patronage of „All Saints“. „Oh when the Saints go marching in, oh when the Saints go marching in, oh Lord, I want to be in that number, oh when the Saints go marching in.“ Over the decades, new versions of the lyrics have emerged again and again; an original text cannot be proven due to early oral tradition. Many artists have taken up the gospel song and released it in their own interpretation, such as Bruce Springsteen with the Session Band at a concert in Dublin: https://www.youtube.com/watch?v=i6eKkirEcgE

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.

Great to get off of the main roads but watch out for pot holes and rough road surfaces. This road certainly needs resurfacing/fixing in places.