4.7
(252)
8,005
riders
223
rides
Road cycling in Windsor and Maidenhead offers varied terrain across royal parks, scenic waterways, and open country roads. The region features expansive natural spaces, including Windsor Great Park and sections of the River Thames, providing diverse backdrops for cycling. Elevations range from 14 to 145 meters, accommodating different fitness levels. The cycling network spans over 1258 km, with significant portions through natural landscapes and alongside rivers.
Last updated: May 5, 2026
4.5
(21)
99
riders
45.4km
01:46
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(2)
39
riders
43.2km
01:46
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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4.6
(12)
447
riders
59.8km
02:42
520m
520m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.5
(4)
422
riders
32.1km
01:41
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.4
(5)
327
riders
67.8km
02:43
220m
230m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.5
(11)
298
riders
51.7km
02:15
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.8
(15)
271
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.9
(12)
211
riders
33.4km
01:24
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.9
(14)
220
riders
32.4km
01:25
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.3
(6)
148
riders
67.7km
02:55
530m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Windsor and Maidenhead
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Nice little quiet climb up Holloway Lane, nothing too crazy gradient wise but fairly narrow if you come across any cars.
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The old Windsor Bridge is an iron and granite, multi-span bridge over the Thames. It connects Windsor and Eton and the Thames Path long distance trail also crosses here. It's thought that there has been a bridge here since the 12th century, this bridge was opened in 1824.
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Road cycling in Windsor and Maidenhead offers a varied landscape. You'll find routes through royal parklands like Windsor Great Park, scenic paths along the River Thames, and open country roads passing through charming villages. The elevation ranges from 14 to 145 meters, providing options from mostly flat rides to routes with moderate climbs.
While many routes are relatively gentle, there are options for those seeking more challenge. For instance, the Marlow Suspension Bridge – Dolesden Lane loop from Furze Platt features over 500 meters of elevation gain, offering a more demanding ride. Similarly, the Marlow Suspension Bridge – Holloway Lane loop from Cookham also includes significant climbs.
Yes, Windsor and Maidenhead offer numerous easy routes. The Pan flat Windsor loop via Drift Road is a popular choice, known for its gentle gradients. Another easy option is the Ascot loop to the Surrey Cycleway, which connects to the Surrey Cycleway and offers varied, accessible scenery.
Many routes offer views of significant historical landmarks. You can cycle past the iconic Windsor Castle, especially on routes like the Windsor and Eton Bridge – Windsor Castle loop from Eton College or the Windsor Castle – Bray Village loop from Windsor and Eton Central. Other notable sights include the Copper Horse monument in Windsor Great Park and the Hawker Hurricane Memorial, which is part of the Hawker Hurricane Memorial – Holyport Village Green loop from Windsor and Eton Central.
Absolutely. The region is rich in natural beauty. You'll find extensive natural spaces, including the vast Windsor Great Park with its ancient woodlands and open grasslands. Many routes follow the River Thames, offering picturesque riverside views. Areas like Pinkneys Green are known for open meadows, and nature reserves such as Cock Marsh and Hurley Chalk Pit provide diverse ecosystems to cycle near.
The region is enjoyable for cycling throughout much of the year. Spring and summer offer pleasant weather for exploring the open meadows and riverside paths. Autumn brings beautiful foliage to the parklands. Even in winter, many routes remain accessible, though conditions may vary. Always check local weather forecasts before heading out.
Generally, no special permits are required for road cycling on public roads and designated cycle paths in Windsor and Maidenhead. The National Cycle Network routes, including sections of Route 4 and Route 61, are freely accessible. For specific areas like Windsor Great Park, cycling is permitted on designated routes. You can find more information on local cycling infrastructure on the Windsor & Maidenhead Council website.
Yes, parking is available in various locations across Windsor and Maidenhead. Many towns and villages along the routes offer public car parks. For routes starting near Windsor Great Park, there are often parking facilities available, though these may be paid. It's advisable to check specific starting points for parking options before your ride.
Windsor and Maidenhead are well-connected by public transport, making many cycling routes accessible. Both Windsor and Maidenhead have train stations with services from London and other major towns. You can often take your bike on trains, though restrictions may apply during peak hours. Check with the train operator for their specific bike carriage policies.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 240 reviews. Reviewers often praise the diverse scenery, from the royal parklands and historic landmarks to the tranquil riverside paths and charming villages. The variety of routes, catering to different fitness levels, is also frequently highlighted as a positive aspect.
Yes, many of the road cycling routes in Windsor and Maidenhead are designed as loops, allowing you to start and finish in the same location. Examples include the Sipp and Spoke – Bottle Lane loop from Maidenhead and the Golden Jubilee Statue – Golden Jubilee Statue loop from Ascot. These circular routes make planning your ride and return journey straightforward.


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