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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.

Discover the rugged beauty of the South Downs on this thrilling gravel adventure.

gravel
57 km
727 m
Tough

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.


Uncover the hidden gems of Hampshire on this thrilling gravel adventure.

gravel
64 km
801 m
Tough

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.


A thrilling gravel route with beautiful downhills

gravel
46 km
617 m
Tough

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.


A scenic road route with a beautiful climb

road
71 km
502 m
Chill

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.


A scenic gravel route with a challenging ascent

gravel
58 km
580 m
Tough

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.


Scenic road route with challenging climbs and historic attractions

road
81 km
722 m
Tough

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.


A beautiful road route with varied terrain and historic highlights

road
72 km
704 m
Tough

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.


Prepare for a thrilling road adventure through Hampshire's hilly landscapes.

road
105 km
971 m
Tough

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.


Journey through Hampshire's scenic landscapes on this thrilling road trip.

road
88 km
836 m
Tough

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.


Embark on a historic journey through Hampshire's picturesque landscapes.

road
112 km
1089 m
Tough

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:

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Kings Worthy

Cycling Paradise with Historical Charm

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Colden Common

Exploring the serene landscapes of Colden Common and nearby South Downs National Park

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New Alresford

Tranquil rides amidst breathtaking countryside

Image of Bishopstoke
Bishopstoke

Begin your cycling escapade amidst the breathtaking nature of Bishopstoke in the United Kingdom's Hampshire and Isle of Wight region.

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Eastleigh

Urban and Rural Cycling Adventures in Hampshire

Image of Fair Oak
Fair Oak

Enjoying the charming countryside views and well-maintained roads of Fair Oak on a road or gravel bike.

Image of Bishops Waltham
Bishops Waltham

Discover the historic charm of Bishops Waltham on your bike

Nearby regions:

Image of Inner London — West
Inner London — West

Urban Cycling Adventure in London

Image of Inner London — East
Inner London — East

Experience the vibrant energy of Inner London — East on a road or gravel bike.

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Outer London — South

Discovering the cycling gems of Outer London — South

Image of Outer London — West and North West
Outer London — West and North West

Scenic rides on the outskirts of London with some challenging climbs.

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Berkshire, Buckinghamshire and Oxfordshire

Exploring the cycling treasures of Berkshire, Buckinghamshire, and Oxfordshire

Image of Surrey, East and West Sussex
Surrey, East and West Sussex

Discover the charm of English countryside and coastal beauty in Surrey, East and West Sussex, United Kingdom.

Image of Gloucestershire, Wiltshire and Bristol/Bath area
Gloucestershire, Wiltshire and Bristol/Bath area

Exploring the scenic countryside and vibrant cities of Gloucestershire, Wiltshire, and Bristol/Bath area on two wheels

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Dorset and Somerset

Diverse cycling opportunities with historical landmarks and charming villages.