The circuit from Hope of Win Hill and Lose Hill is a magnificent day out and makes a fine walk with excellent views on good ground with few route-finding problems - though there are some steep hills to climb.
Start from the centre of Hope village and walk up the Edale road for 300 metres. A small road, marked as a dead end, branches off right. Follow this across the river and continue, ignoring a right fork, to pass beneath the railway. Once under the railway leave this track (which is the old Roman road to Ashop and Glossop) and fork right to climb the steep farm road which leads to Twitchell Farm, which is situated in a magnificent position half-way up the hill.
Climbing up above Twitchell Farm
Sadly, this is no longer a working farm and most of its buildings are holiday cottages. Pass through the former farmyard and continue steeply uphill across the next field to meet a bridle path which crosses the hillside here. Ignore this and continue uphill across the next field, which leads to the boundary of Open Country. The path now trends to the right, making a diagonal ascent of the hillside and levelling off just before meeting a broad path which comes across from west to east and leads to the summit rocks which are about 300 metres to the east. The view on a fine day is well worth the effort of climbing the hill.
Win Hill summit
From the summit turn back to the west and follow the broad path which crosses the summit plateau and then turns north-west to follow the edge of the plateau in a fine position overlooking the lower part of Edale and looking across to Lose Hill. After perhaps 2 kilometres it joins the old Roman road coming up from Hope and you should continue along this in the same direction for another kilometre and a half to Hope Cross, admiring the views of the Jaggers Clough and the eastern end of Kinder.
Hope Cross is an ancient guide post and parish boundary marker situated on the col which separates Win Hill from Kinder and the Edale valley from the Ashop valley. The present marker post is dated 1737, though there was probably a wayside cross here much from a earlier date. It's another fine viewpoint and from here you can see right up the Edale valley and over into the Ashop valley, with Ladybower visible from a little further up the hillside.
Continue along the Roman road for another 200 metres before a bridlepath crosses, coming from the Ashop valley to Edale. Turn left and follow it down across Jaggers Clough and up the other side and then on down towards Edale. The well-made path passes above the farm buildings at Clough Farm and emerges on the Edale road 400 metres east of Nether Booth.
Lose Hill from Edale
Unfortunately you have little option but to walk along the road here, which has to be followed for nearly a kilometre through Nether Booth and under the railway. Then take the farm road which branches off left and leads across the River Noe and up the south side of the valley to Backtor Farm. Continue past the farm but at the next gate branch off the main track to follow the wall uphill and find a good grassy path which climbs steeply uphill to Backtor Nook - the notch in the ridge below Back Tor.
From here it is a short steep climb to the summit of Back Tor and an easy walk along along the too-well-trodden ridge which leads to Lose Hill. It's well worth pausing awhile up here because the views in all directions are really magnificent, but it can be a crowded place on a fine Sunday afternoon.
Hope is now laid out beneath you and to return is an easy descent. The best path follows the ridge to the south-east down to Townhead, but this leaves you with a kilometre to walk back along the road back to the village. An alternative path branches right at a large pile of stones 300 metres below the summit - cross the stile here and follow the fence down initially then straight across the field to Losehill (or Crimea) Farm - which offers refreshments and farm tours. From the east side of the farm another path continues directly across the fields to Hope.