(S/E) From the lion sculpture at Egypt point, follow the esplanade with the sea on your left. Pass Rosetta Cottage where Randolph Churchill met and proposed to his wife, Jennie Jerome, at Cowes week 1883 - Winston Churchill was born in November 1884.
(1) Pass left of Princes Green and after an information board, pass to the left of the Royal Yacht Squadron. This was originally a castle built by Henry VIII in 1539. It was rebuilt in 1850's by Anthony Salvin. Continue on to The Parade - keep to the left and pass a Chinese restaurant.
(2) Turn right into Watchhouse Lane and pass The Union Pub (a walker friendly pub). Turn left into High Street. Pass the Sir Max Aitken Museum (Max Aitken was the son of Lord Beaverbrook) - contains nautical memorabilia in a sail loft. Continue along the High Street. The number of Edwardian facades reflects the heyday of royal yachting. Continue up Shooters Hill- see Jolliffe's art deco shop - originally a shoe shop. Uo on to Birmingham Road with Alexander House and a fine Methodist Chapel. Here turn around and pass Beken's photographie shop- by royal appointment.
(3) Retrace your steps down Shooter's Hill and go left into Cross Street near a car park and by the Painters Arms pub. Turn left into St Mary's Road. Pass a green area on the left with a closed tunnel, which was the route of the railway. At the road junction, turn right into Victoria Road by Cowes Baptist Church. Go to the top of the bill and turn right onto Park Road.
(4) Turn left into Ward Avenue. Cross to the right of the road and follow the grassed area half right to Northwood House, built by the Ward family. Pass an ice house and war memorial damaged in the Second World War. Pass to the right of St Mary's Church, the tower was designed by John Nash. Follow the perimeter of the church to reach its entrance in Church Road. The lodge, by the church on the left, was also built by John Nash.
Go right, down Church Road and turn left into Union Road with its masonic hall of 1846. Keep right into Sun Hill passing Sun Hill House. This part of Old Cowes has some interesting and pleasant architecture. No 32 is the Foresters' Friendly Society 1865.
(5) At the bottom of the hill, turn left into High Street. Herc there is a fine late Georgian façade, and a eustoms warehouse (now Quba sails). Turn left up Market Hill. Here, on the right, there are almshouses, Ward's Cottages, for retired servants from Northwood House. Also, further on the right are Macnamara almshouses of 1881.
Turn right into Castle Road to a junction by an archway. Take the track, Trinity Church Lane and just after the church turn right down some steps. Turn left along Queen's Road which reio111s the esplanade. Continue to your starting point. (S/E)
