The Ventnor parish contains 113 numbered footpaths and bridleways. These combine splendid coastal paths, steep flights of steps through the town and the enchanting and heavily wooded wilderness areas in the Landslip and Undercliff. There are many paths over the Downs which boasts the highest point on the Island St Boniface Down at 241 metres/791feet.
From the top of the Downs it is possible to see right along the south coast of England as far as Beachy Head. In the other direction the higher land way beyond Southampton and Portsmouth can be seen.
The annual Island Walking Festivals take place in May and October attracting some 5,000 visitors as well as thousands of participants from the Island some of whom volunteer as walk leaders. Ventnor always has plenty of walks in these festivals which may have local history or natural history themes.
Ventnor town is a conservation area and still retains its quaint Victorian character. The footpaths are great for exploration and many are composed of steps running up and down the steep landslip on which Ventnor is built.
The most convenient guide to footpaths and bridleways is the Ordnance Survey Explorer Map OL29 The Isle of Wight.
The website of the Island branch of The Ramblers has a map of paths and bridleways www.iowramblers.com/page3.htm
The Definitive Rights of Way map for the island can be searched by area and may be found at www.iwight.com/rightsofwaymaps/
Details of the guided walks offered as part of the Island Walking Festivals (7th-22nd May and 21st-24th October 2011) are published in booklet form and can also be found at www.isleofwightwalkingfestival.co.uk. Many walks take place in the Ventnor area.
If you prefer to choose your own walks, without a guide, The Isle of Wight Ramblers have published four books describing walks in the most scenic areas on the Island. www.iowramblers.com/page5.htm
Leaflets giving details of summer and winter walks are available and a monthly guide to Island guided walks can be found at www.iwight.com/just_visiting/walking/Walks__Events_by_month/
The Ventnor Local History Society has published Ventnor Town Trails available at £1.50 from the Heritage Museum 11 Spring Hill, Ventnor PO38 1PE.