This is what the White Cliffs Countryside Project do all of the time
http://www.whitecliffscountryside.org.uk/includes/tng/pub/tNG_download.php?id=01740a560261c286a02f301208f1e145
There is a good one on 13th June:
East Cliff Oddities - Then and Now
2.5 miles/2.5 hours/Grade 3
A circuit around the outside of Dover's main fortress to see the other historical sights that skirt around the Famous Castle. See the site of Bleriot's 1909 landing, the development of the Eastern Docks at the turn of the 1900's, the Royal Naval Seaplane Station and much more !
Meet at the St James's Church ruins, Woollcomber Street