Originally Posted by
ddeadserious
Work your way up to it. Set a Saturday or something and aim for a 40 mile ride, and if you're feeling good, bump it to 50. Just work your way up to 100, there's no reason to rush into it.
As for the chafing, get some decent bike shorts or bibs and get some kind of chamois butter/cream; others here should have specific recommendations.
Alright. Sounds like a good approach.
The trouble is finding someplace I can ride for long stretches without having to stop at lights etc. But I loathe the Lakefront trail too (at least when it's busy, and especially when it's windy - which is almost always seems to be).