Maidenhead to Windsor loop

Ride level Regular cyclist
Distance 27 mi / 43 km
Type of bicycle Any
Traffic free
Circular route

Georgina Cox is Head of Marketing and Membership at Cycling UK. She was raised in Berkshire and participates in triathlons. Here's her favourite training route.  

Head out of town to Ascot Road. You’ll ride over the M4 and then head onto more open, country roads. Past the village of Holyport, continue on the fairly flat route, turning left at Winkfield Lane, then left onto Drift Road – a very popular, straight, fast road for recreational cyclists, cycle racing including time trials, triathlon and mass participation events.

On reaching the roundabout at the junction back with Ascot Road, you can take a breather. Then turn around and sprint back all the way to the end of Drift Road. Skirting round the bottom of Legoland - head onto Mounts Hill, then left at the roundabout up the A332/Sheet Sleet Road.

This stretch of road up to Windsor is smooth, fast and fun – just take care as there are carparks in Cranbourne Park on your left and some pedestrian crossings. Get your speed up on the dip as otherwise it’s a hard slog back up the other side! Windsor Great Park is on your right with views up the famous long walk to the awesome castle.

Note that the roads around the town are closed off during the Changing of the Guard (check the Windsor castle website for seasonal days / times) so you may need to divert slightly to avoid traffic build ups.

Head towards the town up to the A308, which is then a fast, straight road back into Maidenhead. Or stop off in Windsor to enjoy a wide variety of pubs, shops, riverside, restaurants and of course –LOTS of tourists! If you’re interested, you can also head over the pedestrian bridge into Eton. At the end of the pretty, quaint High Street, you can view the historic school buildings and spot the boys in their traditional tailcoats.