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@bothwell
Ok, I did this at the weekend so can report back.
Gillingham to Ashford is along the national cycle network route 17 and if you follow it religiously, you will probably regret bringing your road bike as you go through the North Downs. It's very rutty, it's very rocky, it's very dusty, and it's very muddy in places. I had 25mm tyres and it was hideous between Westwell and Lenham, with huge trenches in the single track filled with rocks and branches. CX tyres might be ok but I'd have been much happier on my MTB. I was coming from Canterbury towards Gillingham and I decided to bail right after Lenham because I was so knackered from trying to avoid all the obstacles in front of me (though i was also fairly heavily loaded with post-wedding luggage so YMMV).
The scenery is stunning, do it for that alone. I went out on a Sunday where I'd have expected quite a lot of people, but there was virtually nobody along the whole route until I got reasonably close to Maidstone where there were a couple of quad bikers and a guy on a dirt bike, along with maybe four or five mountain bikers. That was it, otherwise very peaceful.
The other half, Ashford to Canterbury, is along national cycle network route 18, and that's road bike friendly if a bit gravelly towards the end as you get onto the Great Stour Walk. I'd have liked something a bit grippier than my Gatorskins going down the two or three small hills in evidence there but as I said, I was fairly heavily loaded so felt that a bit more than I'd have done otherwise.