I am a little late to the party, sorry !!
My family takes a 16 day vacation every year to see family under the same geographical situations that you describe : we hike, we canoe, we go into city, etc.
I bought this coat last year , in black, it is completely waterproof but looks like a spring coat:
http://www.llbean.com/llb/shop.....38;feat=sr
It is a super lightweight coat that is great in your back pack if your are doing something sporty - but it looks fantastic in the city because the silhouette is that of a trench. It is also super for layering since it has no lining and it is a great windbreaker to boot.
I also bought this shoe :
http://shop.nordstrom.com/S/30.....rchresults
It is mega comfortable and looks great with casual skirts, shorts or dresses.
Finally, my favorite site for modern casual/sporty attire is athleta.com;
http://athleta.gap.com/browse/.....?cid=46843
This is a great lightweight skirt that has a pair of shorts underneath - you can ride a in bike them !
As always, bring a scarf and a pair of tights ( footless or not ) to layer.
Happy travels