![Cover image](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/winchester-4.webp)
Discover Winchester's history and countryside on a cycling adventure.
Cycling routes from Winchester
Winchester, located in Hampshire and Isle of Wight, United Kingdom, offers a diverse range of cycling opportunities for both road and gravel cyclists. Cyclists can explore the lush countryside and picturesque villages, as well as enjoy rides along the South Downs National Park. Winchester is also home to the famous South Downs Way, a popular long-distance trail for cyclists and hikers. With its rich history, charming architecture, and excellent cycling infrastructure, Winchester is a top destination for cyclists and tourists alike. The locality ranks 4 on the cyclist perspective scale, offering a combination of scenic routes, historical attractions, and cycling amenities.
The South Downs Gravel Adventure
![Map miniature of "The South Downs Gravel Adventure" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/gravel/275889.webp)
Discover the rugged beauty of the South Downs on this thrilling gravel adventure.
Embark on an exhilarating gravel adventure through the stunning landscape of the South Downs. With a challenging ascent of 727 meters and a distance of 57 kilometers, this route promises to push even the most experienced cyclists to their limits. The trail takes you through the iconic Magdalen Hill Down and Avington, offering breathtaking views along the way. Explore historic sites such as Hinton Ampner and West Meon before conquering the demanding climb of Old Winchester Hill. End the journey with a picturesque ride through Green Hill and Hyde.
![Map miniature of "Hidden Gems of Hampshire Gravel Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/gravel/275820.webp)
Uncover the hidden gems of Hampshire on this thrilling gravel adventure.
Embark on an exciting gravel adventure through Hampshire's hidden gems. With a challenging ascent of 801 meters and a distance of 64 kilometers, this route is perfect for gravel enthusiasts seeking to explore the lesser-known attractions of the area. Start the journey at Winchester Castle, a historic landmark steeped in history. Explore Oliver Cromwell's Battery before reaching the picturesque village of West Tytherley. Ride through Broughton Hill and Kings Somborne, discovering their unique charm. Conclude the adventure with scenic landscapes at Farley Mount and Hyde.
![Map miniature of "Redgrave's Down Gravel Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/gravel/275804.webp)
A thrilling gravel route with beautiful downhills
Embark on this exhilarating 46 kilometer long gravel route near Winchester, featuring charming villages and thrilling downhills. With an ascent of 617 meters, this route offers a moderately challenging ride suitable for gravel enthusiasts. Highlights along the route include Magdalen Hill Down, known for its stunning views, and Hinton Ampner, an elegant country house offering a peaceful oasis for cyclists.
![Map miniature of "Otterbourne Hill Road Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275789.webp)
A scenic road route with a beautiful climb
Experience the beauty of the countryside on this 71 kilometer long road route near Winchester. With a manageable ascent of 502 meters, this route provides a pleasant and scenic ride. One of the highlights along the route is Otterbourne Hill, offering captivating views and a picturesque climb.
Farley Mount Gravel Route
![Map miniature of "Farley Mount Gravel Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/gravel/275821.webp)
A scenic gravel route with a challenging ascent
This distinctive gravel route near Winchester offers a scenic and challenging ride. With a total ascent of 580 meters over a distance of 58 kilometers, this route is perfect for gravel enthusiasts looking for a rewarding ride. The route takes you through beautiful countryside and offers stunning views of Farley Mount, a prominent local landmark.
![Map miniature of "Kilmeston Road Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275785.webp)
Scenic road route with challenging climbs and historic attractions
Explore the stunning countryside on this 81 kilometer long road route near Winchester. With a challenging ascent of 722 meters, this route is suitable for experienced cyclists seeking a challenging adventure. Highlights along the route include Kilmeston, known for its medieval church, and Beacon Hill, a prominent hill offering breathtaking views.
Stockbridge Road Route
![Map miniature of "Stockbridge Road Route" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275876.webp)
A beautiful road route with varied terrain and historic highlights
Embark on this captivating road route near Winchester, featuring varied terrain and captivating highlights. With a challenging climb and scenic vistas, this 72 kilometer long ride is perfect for road cycling enthusiasts. Highlights along the route include Farley Mount, known for its monument and breathtaking views, and Stockbridge, a historic town with charming architecture.
![Map miniature of "Hampshire Hills Road Adventure" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275802.webp)
Prepare for a thrilling road adventure through Hampshire's hilly landscapes.
Embark on a thrilling road adventure through the hilly landscapes of Hampshire. With an ascent of 971 meters and a distance of 105 kilometers, this route is not for the faint-hearted. Experience the beauty of Itchen Stoke and the scenic High Cross. Ride through the challenging Stoner Hill and Torberry Hill, conquering these hilly sections with determination. Discover the idyllic village of West Marden and soak in the rural charm. Explore World's End and enjoy the final climb up Green Hill before reaching St Catherine's Hill and concluding the journey.
Scenic Hampshire Road Trip
![Map miniature of "Scenic Hampshire Road Trip" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275845.webp)
Journey through Hampshire's scenic landscapes on this thrilling road trip.
Indulge in the scenic beauty of Hampshire on this captivating road trip. With an ascent of 836 meters and a distance of 88 kilometers, this route offers a challenging yet rewarding experience for cyclists. Begin with a visit to Ball Down, known for its panoramic views. Discover Fullerton and enjoy the ride along Doiley Hill, offering picturesque vistas. Cycle through the idyllic village of Ashmansworth and conquer the demanding climb of Hyde Hill. Conclude the journey in Kings Worthy, soaking in the beauty of the surroundings.
![Map miniature of "Historic Hampshire Road Trip" cycling inspiration in Hampshire and Isle of Wight, United Kingdom. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/united-kingdom/hampshire-and-isle-of-wight/winchester/road/275807.webp)
Embark on a historic journey through Hampshire's picturesque landscapes.
Explore the historic landmarks and beautiful landscapes of Hampshire on this scenic road trip. With an ascent of 1089 meters and a distance of 112 kilometers, this route offers a challenge suitable for well-trained amateur cyclists. Discover Oliver Cromwell's Battery and North Baddesley before reaching the idyllic Half Moon. Enjoy the scenic route to Bramshaw and Godshill, then marvel at the stunning Whitsbury Castle. Take on the challenging climb of Harnham Hill before reaching the historic city of Salisbury. Ride through Firsdown and Chattis Hill before concluding the journey in Littleton.
Cycling routes nearby:
![Image of Kings Worthy](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/kings-worthy-5.webp)
![Image of Colden Common](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/colden-common-5.webp)
![Image of New Alresford](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/new-alresford-5.webp)
![Image of Bishopstoke](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/bishopstoke-5.webp)
![Image of Eastleigh](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/eastleigh-5.webp)
![Image of Fair Oak](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/fair-oak-5.webp)
![Image of Bishops Waltham](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/hampshire-and-isle-of-wight/bishops-waltham-5.webp)
Nearby regions:
![Image of Inner London — West](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/inner-london-west/roehampton-4.webp)
![Image of Inner London — East](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/inner-london-east/brixton-3.webp)
![Image of Outer London — South](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/outer-london-south/coulsdon-3.webp)
![Image of Outer London — West and North West](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/outer-london-west-and-north-west/brentford-2.webp)
![Image of Berkshire, Buckinghamshire and Oxfordshire](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/berkshire-buckinghamshire-and-oxfordshire/blewbury-4.webp)
![Image of Surrey, East and West Sussex](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/surrey-east-and-west-sussex/dormansland-3.webp)
![Image of Gloucestershire, Wiltshire and Bristol/Bath area](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/gloucestershire-wiltshire-and-bristol-bath-area/weston-super-mare-4.webp)
![Image of Dorset and Somerset](https://images.tarmacs.app/cycling-routes/covers/united-kingdom/dorset-and-somerset/westonzoyland-2.webp)