One thing I have found when walking a long distance path (e.g. the South West Coast Path) is that it is usually easy to follow a route through the country. It is also usually easy to find the way in to the centre of a town even if it's not quite on the 'official route'.
However it can sometimes be difficult to pick up the route out of a town.
One possibility to help with this would be to have a waymark point in a clearly recognisable place say about a mile outside the town. This might be, for instance, at a cross roads.
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