While skyline is pretty and there is lots of scenery, the speed limit is a mere 35mph and anything over they've been heavy on enforcing. We got pulled over last year for going a mere 10mph over. Typically head up there several times throughout the year. The price, however, to enter skyline has risen over each year, increasingly going up... last season it was $10 per bike / car to enter.
Definitely a doable ride to go from front royal to charlottesville, but it's going to be a long day of doing relatively slow speeds due to law enforcement on the drive. Once you get down to the BRP, things open up and it's a lot nicer, relaxed ride. Also, fall and spring on skyline tends to be pretty crazy on the weekends due to the colors coming out and in the fall, the fall colors. So you'll get a lot of traffic, sightseeing and occassional backups. If I were planning a trip..I'd ride down skyline and take one of the many backroads below the mountain to head back up, occassionally crossing over skyline on 33 and / 211, which are both nice for the twisties up and down the foothill we call a mountain..haha (the backroads are fantastic, pretty scenic and some relatively backwoods style roads...you can hit gravel most / part of the way or not at all). Just my .02
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