The worst I have been out in was a day gusting to about 50 MPH in Plymouth County, MA. The Plymouth airport had 12 hrs of sustained winds 22-32 with a max gust of 55 MPH. Once I had the tailwind, it was quite enjoyable! With the tailwind at one point, I was crossing on a highway bridge on a small (like 1%) incline, and sprinting up to 40 MPH. Fortunately though, with so many trees around, the only difficult headwinds were wider roads facing directly into the wind itself (US 44 being the worst).

Before doing that, I didn't know what the worst I'd ride in is. I honestly think that a sunny day, cold front coming through after a storm, would not get any worse than this, save for the upper Midwest. I think if it could be worse, I'd probably pass.