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@mooks
I've done something similar to that ride geared, since my parents live in West Moors. There are a couple of hills that can take it out of you, but nothing that can't be done fixed. The descents (depending on which way round you go) aren't too demanding either.
The B3082 around Badbury Rings/Kingston Lacey is really exposed though, and the ups and downs along that road can take it out of you - make sure you take it in turns to lead on that bit.