I do a 2-way ride where the turn around point is Hampton Beach, NH, exactly 50 miles east of my home. I vividly remember two times where the winds shifted from being from the ocean to being from land right as I turned around. It's almost comically ironic when it occurs, but it definitely is not funny at the time. OTOH, on those rare days where the tailwind turns around just as you do, you end up feeling like Superman. That almost never happens to me, though, as I intentionally will do the in-your-face part on the front end of the ride and the shift is way too unpredictable to deliberately time it that way if you start with the wind at your back.

If the forecast is for winds, though, I usually try to pick a route where it's cross-winds. That did not work well much this year for me, the winds just seemed to be out to get me no matter what I did.