63 miles and you come back. I bought a new wide glide last sept. My 1st new bike. I've ridden older bikes all my life. When I got on the bike I took off riding, after riding a few hours I notised the sun was going down. I had rode over 150 miles away from the pad. I stopped an grabbed a burger and a redneck budweiser and rode home. Took the next day off and rode some more. You got to get yer butt conditioned. Git out of the house and ride. Stop and take break's and walk around some too.
yer just not in riding shape yet. Nothin wrong with the bike.

 

Get up north of the ILL / Wis border onto some nice roads and that Sporty will feel a lot more comfy.... Still windy here in the Chicago area,once it gets warmer and the winds calm down it'll be better.

 

Thanks Chiabate, will definitely consider! Cardboard no offense but have you ever sat on a stock Sportster seat for a long time? T3, I'm looking forward to heading up that way. Meant to do it last year but never had the time.

 

Unless the large majority of your rides are very short I'd work on making the bikecomfortable first, then worry about performance upgrades if it were me. If you're miserable you won't ride as much, so maybe a different seat? Extended footpegs, etc.