How I get there is my own business and only mine but I will share them with you.
Went in '04, '06 and '08.
In '04, I left Worcester, MA on Thu, bike loaded up for the ride of a lifetime, hooking up with a friend in New Jersey and stopping along the way at various houses of friends met on the net, along the way, arriving in Sturgis on Tue afternoon. Partied nightly, mostly in the campground after riding the Black Hills, etc during the day. Left Sun, putting 667 miles on the clock, Mon clocked 712 miles and Tue clocked another 535 miles, arriving home late afternoon.
In '06, I had planned to ride with the same buddy and two others but about 10 days prior to leaving, an opportunity presented itself to put my bike on a truck and fly out. My two close buddies were doing the truck/fly route when one had to cancel. I took his place rather the letting one go alone, an option I will never regret. I boarded a plane in Boston at 6 am and was at my hotel in Rapid City by noon time, bike waiting for me. My buddy was on a later flight. Two days later we were on our way to Jackson Hole, Yellowstone, Cody and Beartooth Pass. Yeah, we went the reverse way of the way the masses do! Did 1,500 miles just in Wyoming and Montana.
Move on to '08 and these two are planning on trailering their bikes and riding in a conversion van. Gas is up over $4 a gallon and I want nothing to do with that trip. The reason they wanted to do that is because they "figured" the price to truck/fly would be higher. I made a few calls and booked the three of us for $1,800 each, $300 cheaper than the '06 cost. We had 9 days of fun in the Sturgis area, again not a regret.
We're doing it again next year and a few others are interested in joining us as well. This time we're thinking of using the truck/fly route as a mere drop-off/pick-up method and getting on the road to Colorado/Utah.
I just did a four-day, 1,100 mile trip. My old behind can't handle more than that on the Deuce. Someday I may step-up and get me one of the VistaCruiser type bikes.
ennis