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Hulsroy
The Kennet & Avon canal would cover a good chunk of the route. Mixture of surfaces from gravel towpath to going across a few fields.
It's a Sustrans route (http://www.sustrans.org.uk/ncn/map/route/kennet-and-avon-cycle-route)
Before that, to get to Reading, you can follow either the Thames from SW London towards Reading. Much of that is off-road. Or the canal from Hanwell / Southall. They both meet up around the Jubilee River near Windsor.