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Welcome to Portland! I'm an avid rider here, and I have a few suggestions for you when riding in the 'off' months. First, get a fog shield for your helmet. When riding in cooler, wet weather, it's a godsend. Second, have good rain gear handy - even if you simply store it in a tank bag or seat bag. Rain comes upon us somewhat unexpectedly from October through June, so having proper gear handy is always a plus. Finally, purchase quality Gore-Tex, lined, overpants and coat. Also, keep a dry towel handy to clear your facemask from time to time. RE: type of bike? Anything is fine. I ride a Triumph Sprint ST, and I love it. It's great for the longer distances and works well in the many curves we have here. From Portland, there are great rides to Mt. Hood and Mt. St. Helens, the Coast, and throughout the Columbia Gorge. Believe me when I say that you will NOT be disappointed with the many, many available rides. It's truly a biker's paradise. I hope this helps.
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