Right now that is the big debate!
Ride, or trailer part way...
We are weighing options. We live in Indy, so he says it's around 1100 miles each way.
I'd love to ride it all the way. His bike and my lack of riding experience are running us into questions. His bike currently hits the gas light about every 100 miles. So he may need a bigger tank before we can do it. But we shall see!
Would certainly be a great late honeymoon adventure to ride the whole way!
A bit slower and longer if you stay off of the freeways riding but infinately more enjoyable. As I noted I'd plan on at least 1,200 miles and 4-5 days if you ride to Sturgis.
While the fuel light comes on at about 100 miles the range is over 165 on the highway but I always stop for fuel every 100 miles and suggest it. It's good to take a short break after that many miles of riding to avoid fatique.
You do have the option of riding there, then dropping the M/C off at any Harley dealer and they will ship it home for you. I believe that the cost is $500 but you'd need to check on that. I believe I read that in the HOG literature. Then you can fly home from wherever you drop the M/C off.
On a personal note I've found the journey to and from an event to be equal or better than the event itself. The sights I see and the people I meet on the highways and byways are one of the most enjoyable parts of any road trip I take. That and the actual riding is what it's really all about even when you make it to an event like Sturgis.