![Cover image](https://images.tarmacs.app/cycling-routes/photos/united-kingdom/gloucestershire-wiltshire-and-bristol-bath-area/8684975250/fifehead-magdalen-2.webp)
Shaftesbury Hill Challenge
A road cycling route starting from Shaftesbury
Conquer the rolling hills of Shaftesbury on this challenging road cycling route.
Map
![Map miniature of "Shaftesbury Hill Challenge" cycling inspiration in Dorset and Somerset, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/dorset-and-somerset/shaftesbury/road/181276.webp)
Experience the beauty and thrill of cycling through the undulating landscapes near Shaftesbury. This road cycling route offers a satisfying challenge for experienced cyclists, with a total ascent of 328 meters over 38 kilometers. Enjoy breathtaking panoramic views of the surrounding countryside as you conquer Duncliffe Hill, Fifehead Magdalen, Bourton, Castle Hill, and Motcombe. Discover the medieval castle remains at Castle Hill and soak in the tranquility of Motcombe Wood along the way. This route is a true gem for road cycling enthusiasts seeking a satisfying and scenic biking adventure.
road
38 km
328 m
Tough
Route profile
Highlights on the route
0 km
0 km
Start: Shaftesbury City centerShaftesbury: Cycling in Shaftesbury: Scenic routes through rolling hills.
Shaftesbury is a locality located in Dorset and Somerset, United Kingdom. Road and gravel cyclists will find Shaftesbury to be a fantastic destination offering a mix of scenic routes through rolling hills and captivating countryside views. The area is known for its stunning landscapes, with its most famous feature being Gold Hill, a picturesque cobblestone street. Cyclists can explore the local trails and challenging climbs in Cranbourne Chase, making Shaftesbury a great choice for those seeking diverse cycling experiences.3 km
3 km
Duncliffe Hill211 mPeakConquer Duncliffe Hill, with its steep gradients, and reward yourself with magnificent panoramic views of the countryside.
10 km
10 km
Fifehead MagdalenVillageEmbark on the challenging ascent of Fifehead Magdalen and experience the exhilaration of reaching the summit.
20 km
20 km
BourtonVillagePass through the picturesque village of Bourton, known for its charming cottages and idyllic scenery.
25 km
25 km
Castle Hill163 mPeak ViewpointExplore the historic Castle Hill and discover the remains of a medieval fortified structure.
34 km
34 km
MotcombeVillageEnjoy a peaceful ride through the scenic woodland of Motcombe, surrounded by nature's beauty.
38 km
38 km
Finish: Shaftesbury City centerShaftesbury: Cycling in Shaftesbury: Scenic routes through rolling hills.
Cycling routes from Shaftesbury:
The Gravel Route of Green Landmarks The Gravel Ride of Hills and History The Ultimate Gravel Adventure Road Cycling Tour of Tranquility The Great Dorset Challenge Gravel through Rural Dorset and Somerset Challenging Road Loop through Dorset and Somerset Scenic Road Circuit around Dorset and Somerset Scenic Countryside Road Ride around Shaftesbury Gravel Adventure through Dorset and Somerset Countryside Shaftesbury Hill Challenge Donhead St Andrew, Winkelbury Hill, Pentridge Hill Loop Gravel Adventures of Shaftesbury Shaftesbury Heritage Loop
Cycling routes nearby:
![Image of Gillingham](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/dorset-and-somerset/gillingham-5.webp)
![Image of Tisbury](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/gloucestershire-wiltshire-and-bristol-bath-area/tisbury-5.webp)
![Image of Stalbridge](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/dorset-and-somerset/stalbridge-5.webp)
![Image of Henstridge](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/dorset-and-somerset/henstridge-5.webp)
![Image of Templecombe](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/dorset-and-somerset/templecombe-5.webp)