The Winter Challenge starts at the Scout Hut on Maple Drive close to the junction with North Leas Avenue. Leave the Scout Hut and turn right down North Leas Avenue. Turn left into Northstead Manor Drive and descend to the roundabout. Cross using the pedestrian crossing with care and patience, and continue right, past the open-air pool and to the Corner Cafe. Checkpoint 1 — Disc drop.
From the Corner Cafe, along Royal Albert Drive alongside the beach, soon take the path, behind huts, uphill towards the Castle. Reach Queen's Parade and keep to the path ahead where the road turns right. Turn right before the path continues ahead to the Castle, and soon left by St. Mary's church. Checkpoint 2.
Descend by any alternative way to the Harbour or use steps on the right, and a short stretch of road, to descend to the Harbour. Turn right and follow the sea front, or cross the sands, to the Spa. Checkpoint 3.
Continue along past the Spa and climb the steps immediately past the cliff lift. Turn left along the Esplanade. Use any route to the right to reach Filmy Road. Turn left. Cross and turn right, down Belvedere Road. Cross Filmy Road, A165, and into Mount Side. Turn right at the junction, cross, and go over the stile quickly reached. Follow the path ascending half right to a second stile. Continue to ascend, and, just before the summit, take the first well-used path to the War Memorial on Oliver's Mount. Checkpoint 4.
Turn right and follow the metalled road, past a junction, and as it descends quickly and sharply right, past the junction with Weaponess Lane, to join Mere Lane. As you near the Mere, Look for the 2 footbridges which link the island to the Mere shore. Checkpoint 5.
Cross these with care avoiding slipping! Turn right along the lake-edge path to Queen Margaret's Road. Turn left, over the railway, and cross Seamer Road with care. Slightly right, go down Edgehill Road. (Scarborough A.F.C.) Just before the end of Edgehill Road, take the track on the left, ascending to an entry gate to a caravan camp. Follow the track, which bears right and ahead through the lines of caravans. Turn right, along the wide track, crossing a stile on the left before continuing ahead. After a short descent, reach a bridleway junction where a footpath passes through a gate on the left. Take the footpath across the field, at about 30 uphill, to a stile at the edge of the wood. Cross and ascend the steps and continue along the path to reach the A170 at Jacob's Mount. Checkpoint 6 (here or at the gate below).
Cross, again with care, to the stile opposite. Cross and ascend through the field diagonally right to reach the edge of Rowbrow Wood on your right. Reach a gate and follow the wide track ahead as it skirts the wood, past Seamer Beacon and several transmitters, until it enters the wood. Keep to the main, level track as it bends left into Raincliffe Woods. Where this main track narrows and descends, bear left onto the narrow path, which runs close to the field boundary above the wood. After about 1½ miles, at a small dip, a wide track comes up on your right. Not so clear is a narrow path, slightly to the right ahead, which descends moderately steeply. White markings on trees may remain to help identify this. Descend to a path junction, turn left, and reach a wider track. Turn right and descend to the road below. Cross and take the path through the trees opposite to emerge at the picnic site. Checkpoint 7.
You may take the path left at the far end, through the trees, to reach the Forge Valley road. Beware slippery boards! Alternatively use the road. Turn left round the road junction and into Forge Valley. Pass a bird observation area and take a narrow path just before a dip in the road, which bears right and downhill to the bridge over the River Derwent close to a car park. Cross and turn right along the riverside paths, taking care on the wooden boards. Cross a stile and emerge into a meadow. The correct path bears left uphill but is overgrown, so follow the clear track ahead, which soon rises to the left and later descends to gateways. Pass through and follow the waymarked path along the low embankment by the river. A short distance before the end of the field, hidden by gorse bushes, is a gateway and stile on your right. Cross and turn left towards another stile. North Stile Cottage is on the hillside above. The path continues clearly ahead now, close to the river, before rising along the fence side to join the track, through a gate, into Cockrah Foot. It may be tempting to climb the hill to reach the track shortly after passing below the cottage for better viewpoints. The track becomes a road. Turn right at the junction by Rose Cottage and cross the stile on the left, just before the bridge, and follow the embankment past Wrench Green to a footbridge over the Derwent. Cross this and the road reached, now close to Hackness. Over the stile almost opposite, the path rises, bearing a little to the right, to reach the edge of woodland. Turn left along the edge and cross the stile on the right, just before a fence, and enter the wood. Follow the clear path left and soon emerge into the field above Hackness Hall and lake. Take the waymarked grass track ahead, which shortly descends, bearing left, to a stile. Keep to the often muddy path ahead as it gradually descends to the road. Checkpoint 8.
Follow the road left, past the hall and church, and over the Lowdales Beck Bridge. Turn right, along the road to Lowdales. After about a mile reach a footpath sign on the left. Take the path, which quickly bears right over a field, and make sure that you hove reached the narrow path, which climbs steadily uphill through a plantation. This leads to an open field above. Turn right, along the edge. Cross a stile into the last field before Broxa and bear left towards a gate to the right of the farm. Reach a lane and pass a barn on the left. Checkpoint 9.
At the lane end, pass through the field gate on the right and reverse direction along the hedge side, turning left at the field corner. (THE ROAD IS OUT OF BOUNDS!) Descend along the track reached at the end of the field, and cross the stile at the sharp bend. (SELF-CLIP HERE OR AT THE STILE BELOW) Descend through woodland to a stile below, Cross and walk over the field to a gateway and a beckside track. Soon reach a stile opposite a cottage. Cross and ford, or jump over, the beck and ascend to a track. Turn left. Ignore a footpath and take the bridleway, through a gate on the right, which bears right, uphill, and enters woodland. Keep ahead where a track crosses, and, soon after reaching almost level ground, follow the main track right at a junction. Turn left at a T-junction, along a forest road. Pass an area of smaller trees and, at a junction, take the track bearing right. Right turn and later left turn at the next 2 junctions to reach the car parks at Reasty Bank. Checkpoint 10.
Cross the road to the viewpoint and take the right hand, level, track through the woodland. Follow this for about ½ mile until a slightly obscured path is reached, bearing left downhill. Emerge into a field. Continue ahead, descend bearing left and then alongside the fence to reach a gate and the road at Surgate Brow. Turn left and walk down to the sharp bend in the road. Here take the track to the right, through gates and alongside, NOT into, a plantation. Turn right at the field corner, and follow the gated track to Kirkless Farm, pass right and then quickly left through the farmyard and continue along the now surfaced road to a road junction. Cross straight over and keep to the road ahead to Burniston and the A17l is reached. Turn right along the main road, crossing with care, and turn left, along the minor road immediately before the 'Three Jolly Sailors' inn. Cross a bridge over a beck. The disused railway is just ahead. Turn left into the farmyard and right to a barn. Checkpoint 11.
Return to the road and turn left and take the steps up to the old railway, on the right just before the bridge. Turn right. Carefully cross the Al65, and, a little to the left, locate the small gate leading back to the railway track. Follow this to Scalby. Leave the track through a gate and path to the left, and follow the estate road, keeping left, down to Station Road. Cross and a little to the right, enter Chichester Close. Turn right, after passing the Wardens house, and walk round to the back of the close. A gate here leads once again onto the old track. Scalby Beck is crossed, a new estate passed through, and a bridge walked under. A church is soon seen on the right. Turn left, ascending a narrow path immediately before the bridge here to reach Cross Lane. Walk ahead, crossing once again with care. Turn right, down Newlands Park Drive, which soon merges into North Leas Avenue. The Scout Hut is soon reached on your right - Well Done!