Dorset’s countryside is a cycling paradise, offering rolling hills, quiet country lanes, historic villages, and scenic climbs. Whether you’re looking for gentle rides, long-distance loops, or challenging climbs, the areas around Sherborne, Shaftesbury, and Gillingham provide some of the best cycling routes in the South of England.
Here are some of the top cycling routes near each town, including Google Maps links to help you find the starting points!
🚴♂️ Best Cycling Routes Near Sherborne
1️⃣ Sherborne & Blackmore Vale Loop – Classic Countryside Ride 🌿🏡
📍 Start: Sherborne Abbey, Sherborne
• Distance: 55 km (34 miles)
• Difficulty: Moderate
• Terrain: Rolling country roads, farmland, small villages
🚴♂️ Why Ride It?
• A gentle loop through Blackmore Vale, one of Dorset’s most beautiful rural areas.
• Passes through Yetminster, Bradford Abbas, and Stalbridge.
• Stunning views of Dorset’s rolling hills without too many steep climbs.
📌 Best for: Riders looking for a scenic countryside ride with a mix of easy and rolling terrain.
2️⃣ Sherborne to Cerne Abbas – The Abbey & Giant Ride ⛰️🏛️
📍 Start: Sherborne Castle, Sherborne
• Distance: 50 km (31 miles)
• Difficulty: Moderate to Challenging
• Terrain: Hills, valleys, and quiet rural lanes
🚴♂️ Why Ride It?
• Scenic ride through Dorset’s hidden valleys, with some rolling climbs.
• Stops at Cerne Abbas, famous for the Cerne Abbas Giant.
• A mix of fast sections and slow, steady climbs with rewarding descents.
📌 Best for: Intermediate riders looking for a varied and interesting route with historical landmarks.
🚵♂️ Best Cycling Routes Near Shaftesbury
3️⃣ Shaftesbury & Gold Hill Climb – The Ultimate Challenge 🏔️⛪
📍 Start: Gold Hill, Shaftesbury
• Distance: 45 km (28 miles)
• Difficulty: Challenging
• Terrain: Hills, steep climbs, scenic countryside
🚴♂️ Why Ride It?
• Takes on Gold Hill, one of England’s most famous (and toughest!) cycling climbs.
• Stunning views across the Dorset Downs and Cranborne Chase.
• Mix of fast descents, rolling roads, and steep climbs for a challenging ride.
📌 Best for: Experienced cyclists looking for a serious hill climb challenge in a beautiful setting.
4️⃣ Shaftesbury to Cranborne Chase – AONB Adventure 🌲🏞️
📍 Start: Castle Hill Viewpoint, Shaftesbury
• Distance: 65 km (40 miles)
• Difficulty: Moderate
• Terrain: Open countryside, quiet backroads, rolling hills
🚴♂️ Why Ride It?
• A beautiful ride through Cranborne Chase, a designated Area of Outstanding Natural Beauty.
• Mostly quiet roads with occasional traffic-free sections.
• Features rolling terrain and short but challenging climbs.
📌 Best for: Gravel or road cyclists looking for a long-distance adventure through quiet, scenic countryside.
🚲 Best Cycling Routes Near Gillingham
5️⃣ Gillingham & Stour Valley Loop – Riverside Cycling 🌊🚵♂️
📍 Start: Gillingham Train Station
• Distance: 50 km (31 miles)
• Difficulty: Easy to Moderate
• Terrain: Quiet lanes, river paths, open countryside
🚴♂️ Why Ride It?
• Follows the River Stour, offering a mix of fast roads and scenic countryside.
• Passes through Mere, Bourton, and Stour Provost.
• Minimal traffic, making it perfect for peaceful, scenic riding.
📌 Best for: Beginner to intermediate cyclists looking for a gentle but rewarding ride through Dorset’s beautiful countryside.
6️⃣ Gillingham to Longleat – Ride Through the Safari Park! 🦁🌳
📍 Start: Gillingham Town Centre
• Distance: 70 km (43 miles)
• Difficulty: Moderate to Challenging
• Terrain: Country lanes, forest roads, rolling hills
🚴♂️ Why Ride It?
• A unique cycling experience that takes you near Longleat Safari Park.
• Fantastic views of the Wiltshire and Somerset countryside.
• Includes some challenging climbs and fast descents.
📌 Best for: Riders who want a long ride with an interesting destination and fun wildlife spotting.
🌟 Bonus: Multi-Town Cycling Challenge
🔹 Sherborne ➝ Shaftesbury ➝ Gillingham Loop – 85 km (53 miles)
• Difficulty: Challenging
• Terrain: Hills, valleys, fast descents
🚴♂️ Why Ride It?
• A full-day ride connecting all three towns.
• Includes scenic valleys, historic towns, and tough hill climbs.
• A great training ride for those preparing for long-distance sportives.
📌 Best for: Advanced cyclists who want a full-day adventure with varied terrain.
🚴♂️ Tips for Cycling Near Sherborne, Shaftesbury & Gillingham
✔️ Road or Gravel? – Most routes are road-friendly, but some have gravel sections (check in advance).
✔️ Watch for Traffic – These areas have quiet roads, but be careful near villages and on faster lanes.
✔️ Refuel Smart – The best café stops are in Sherborne, Shaftesbury, and Gillingham town centres.
✔️ Prepare for Hills – Dorset and Wiltshire have some steep but rewarding climbs!
✔️ Weather Ready – The countryside can be exposed—bring waterproofs & layers in unpredictable weather.
🔥 Final Thoughts: Where Will You Ride First?
The Sherborne, Shaftesbury, and Gillingham areas offer some of the best cycling routes in Dorset and Wiltshire. Whether you’re looking for gentle countryside loops, historic routes, or steep climbs, there’s a ride for everyone.
🚴♂️ Have you cycled these routes? Share your experiences & tips in the comments below! 🔥💬
