Winter Hill and Cookham Dean Circular Walk

View to Hedsor from Winter Hill Golf Course


Start & Finish: Cookham Moor Public Car Park, 2 High Street, Cookham, SL6 9SG
Distance: 10.1 km (6.3 miles)
Elevation change: +/- 118m
GPX File: get via Buy Me a Coffee
Other routes touched (walk): Thames Path, Shakespeare’s Way, The Chiltern Way Berkshire Loop
Other routes touched (cycle): Round Berkshire Cycle Route
Pubs / Cafes on route: The Bounty, Bourne End, The Mole and Badger, Cookham Dean
Map: OS Explorer Map (172) Chiltern Hills East
Links: Cookham, Bourne End, Winter Hill, Cookham Dean, National Trust Maidenhead and Cookham Commons


This is a short circular walk mixing the flat ground of the Thames Path and a loop of nearby Winter Hill. Start at the National Trust Car Park (free to members) on Cookham Moor and walk in a northerly direction to the Thames. Take a left and follow the Thames Path in a northerly direction until the Bourne End rail bridge. Leave the Thames Path here as it crosses the bridge and keep to the south side of the Thames, now starting to curve toward the west.

After 3 km from the Car Park, the path takes a right-angle behind some riverside houses. Cross the field heading south-east to and take the path that climbs the hill heading in a south-westerly direction. Follow this path for 1.6 km until you reach Quarry Wood Road. Along the way you’ll see some great views across the river to Little Marlow and the Chiltern Hills beyond.

When you reach Quarry Wood Road take a right onto it and follow it for approx 100 metres and cross over to a footpath on the left hand side of the road. Be very careful here as there’s no pavement on this road and cars can be quite fast. Be visible and keep to the right facing oncoming traffic.

Follow the path in Quarry Wood in a south-westerly direction for 200 metres to a path junction. Take a left and follow this path for another 200 metres to the corner with Quarry Wood Road. Take a right and follow the path on the south-eastern edge of the Wood for 300 metres. Cross Over Grubwood Lane and take the path through the field, up the hill next to the llama enclosure. Continue to the woods at the top of the hill where you’ll now be on the Chiltern Way Berkshire Extension.

Once in the Woods, take a left and follow the Chiltern Way. This will take you past the Mole And Badger pub, round the Cricket Common and down to Dean Lane. Follow Dean Lane in an easterly direction to Alleyns Lane having left the Chiltern Way. Follow Alleyns Lane to Broadcuts Lane, then continue over the lane and along the path to Terry’s Lane. Continue over the next field to rejoin the Chiltern Way Berkshire Extension. Take the right hand path to follow the Chiltern Way across Winter Hill Golf Course to the bridge over the railway.

Once over the railway take a right and follow the path to Terry’s Lane. Take a path on the left and follow this to the east then south, following Stroud Water back to the National Trust Car Park.