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Cycling paradise near historic Windsor Castle and the River Thames.


Cycling routes from Windsor

Windsor is a great locality for road and gravel cycling, with its picturesque countryside and beautiful landscapes. The roads are well-maintained and there are plenty of cycling routes to explore. Cyclists can enjoy the stunning views of Windsor Castle and the River Thames as they ride through the town. In addition, the nearby area offers some well-known climbs and cycling spots, such as the Chiltern Hills and Burnham Beeches. Overall, Windsor is a popular destination for cyclists, offering both challenging climbs and scenic routes.

Explore the scenic Thames Valley on this thrilling gravel ride

gravel
84 km
291 m
Tough

Discover the beauty of the Thames Valley on this 84 km gravel adventure. With a total ascent of 291 meters, the route takes you through picturesque towns and stunning landscapes. Suitable for experienced gravel riders.


Embark on an exhilarating road cycling journey through Buckinghamshire

road
68 km
536 m
Tough

Get ready for an adrenaline-fueled road cycling adventure through the stunning landscapes of Buckinghamshire. This route offers a challenging ascent of 536 meters over a distance of 68 kilometers. Begin your journey with a visit to Dorney, home to the iconic Dorney Lake and a hub for water sports enthusiasts. Take a moment to catch your breath and admire the southern viewpoint of Cliveden, offering breathtaking vistas of the surrounding countryside. Ride through the scenic beauty of Hazlemere and soak in the tranquility of its landscapes. Explore the charming village of Latimer, known for its historical buildings and idyllic setting. Marvel at the natural charm of Fulmer and take a moment to appreciate its stunning uniqueness. Conclude your adventure in Eton, a town renowned for its illustrious school and outstanding architectural heritage.


Experience the rolling hills and charming villages of the Chilterns and Missenden on this exhilarating gravel route

gravel
73 km
388 m
Tough

Embark on a scenic 73 km gravel loop through the Chilterns and Missenden, featuring a challenging ascent of 388 meters. This ride showcases the idyllic countryside and offers a taste of traditional English village life. Suitable for intermediate to advanced gravel riders.


Embark on a scenic road ride with Windsor Castle as your starting point and explore the beautiful surrounding areas

road
53 km
371 m
Tough

Discover the beauty of Windsor and its surrounds on this 53 km road cycling route, boasting an elevation gain of 371 meters. From historic landmarks to charming villages, this ride provides a glimpse into the region's rich history and natural beauty. Suitable for intermediate road cyclists.


Uncover the hidden gems of Buckinghamshire

gravel
60 km
127 m
Tough

Embark on an exciting gravel ride through the breathtaking landscapes of Buckinghamshire. This route presents a challenging ascent of 127 meters over a distance of 60 kilometers. Begin your journey with a visit to Windsor Castle, a symbol of British royalty for over 900 years. Explore the scenic town of Iver, known for its charming architecture and peaceful ambiance. Ride through the picturesque landscapes of Ruislip and immerse yourself in its natural beauty. Discover the hidden gems of Northolt and its vibrant local community. Experience the thrill of spotting planes at the 27L Runway Viewing Area in Myrtle Avenue. Marvel at the historical charm of Bedfont and witness the tranquil beauty of Egham. Conclude your adventure with a sense of accomplishment and a newfound appreciation for Buckinghamshire's beauty.


Unveil the scenic wonders of Berkshire, Buckinghamshire, and Oxfordshire

gravel
78 km
821 m
Savage

Embark on an epic cross-county gravel adventure that takes you through the diverse landscapes of Berkshire, Buckinghamshire, and Oxfordshire. Challenge yourself with an ascent of 821 meters over a distance of 78 kilometers. Begin your journey in White Waltham, a village known for its idyllic charm and aviation history. Explore Henley-on-Thames, known for its world-famous rowing regatta and stunning riverside views. Visit Stonor, home to one of the oldest manor houses in England, boasting rich history and impeccable gardens. Marvel at the breathtaking landscapes of Winter Hill and immerse yourself in the natural beauty of the surroundings. Ride through the charming town of Maidenhead, nestled on the banks of the River Thames, and take in its picturesque scenery. Conclude your adventure in Eton, renowned for its prestigious school and quintessential English charm.


Discover the scenic beauty of the road to Eton

road
44 km
70 m
Tough

Embark on a scenic road cycling route that showcases the natural beauty of Berkshire, Buckinghamshire, and Oxfordshire. Challenge yourself with a moderate ascent of 70 meters over a distance of 44 kilometers. Begin your journey in Eton, renowned for its prestigious school and quintessential English charm. Explore the tranquil beauty of the Temple Gardens and immerse yourself in the serenity of the surroundings. Ride through Hayes End and take in the picturesque landscapes that this charming town has to offer. Stop by the 27L Runway Viewing Area in Myrtle Avenue and experience the thrill of plane-spotting as majestic planes take off and land. Visit Bedfont, a town steeped in history and surrounded by idyllic landscapes. Conclude your ride in Windsor, home to the iconic Windsor Castle and a treasure trove of architectural wonders.


Step back in time as you explore the historic sites of Berkshire on this road cycling adventure

road
59 km
335 m
Tough

Embark on a 59 km road cycling journey through Berkshire and soak in the rich heritage of the region. With a challenging ascent of 335 meters, this route offers a perfect blend of history, nature, and picturesque countryside. Suitable for intermediate road cyclists.


Discover the historic Windsor Castle and pedal through the picturesque Thames Valley.

gravel
59 km
91 m
Tough

Embark on a scenic gravel loop from Windsor, exploring the charming towns and countryside of Berkshire, Buckinghamshire, and Oxfordshire. This route offers a unique blend of heritage sites, river views, and rolling gravel trails. Traverse the tranquil routes dotted with idyllic villages and landscapes that have inspired countless writers and artists. Take in the captivating views and immerse yourself in the serenity of the Great British countryside.


Take on the demanding Surrey and Kent hills as you push yourself to the limit on this epic road cycling route

road
109 km
593 m
Savage

Prepare for a challenging 109 km road cycling adventure through the hills of Surrey and Kent, featuring a grueling ascent of 593 meters. This route offers a true test of endurance and rewards riders with breathtaking views and iconic landmarks. Suitable for experienced road cyclists.


Cycling routes nearby:

Image of Eton
Eton

Idyllic cycling in historic Eton

Image of Datchet
Datchet

Picturesque Cycling in Datchet

Image of Eton Wick
Eton Wick

Cycle Through the English Countryside in Eton Wick: Charming Routes Await!

Image of Slough
Slough

Discover the cycling opportunities in the scenic countryside near Slough

Image of Old Windsor
Old Windsor

Cycling Through Time and Nature in Old Windsor

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Colnbrook

Colnbrook, South East England: Discover the English Countryside on Two Wheels

Image of Farnham Royal
Farnham Royal

Tranquil Cycling Retreat in Farnham Royal

Image of Egham
Egham

Exploring the picturesque cycling routes and immersing in history in Egham, United Kingdom.

Image of Stoke Poges
Stoke Poges

Serene cycling in the heart of the UK's countryside

Nearby regions:

Image of Leicestershire, Rutland and Northamptonshire
Leicestershire, Rutland and Northamptonshire

Picturesque regions with rolling hills, charming market towns, and historic landmarks.

Image of Bedfordshire and Hertfordshire
Bedfordshire and Hertfordshire

Exploring the picturesque countryside and historic towns of Bedfordshire and Hertfordshire.

Image of Inner London — West
Inner London — West

Urban Cycling Adventure in London

Image of Outer London — South
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.

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 Hampshire and Isle of Wight
Hampshire and Isle of Wight

Diverse landscapes with challenging climbs, picturesque countryside, and coastal routes, perfect for immersing in the British cycling scene.

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