Originally Posted by davidmcowan
Yeah... I feeling like if I do it I could just roll the flip flop hub so that if I'm feeling really tired I can just flip it so I can coast. I guess my fears are more about being able to keep up with my pack of friends (all non cyclists) and not totally conking out so that I can't have fun at night. Again, I ride a lot but I am just a little fearful.

If I rode my fixed gear though I wouldn't need to worry about rack and panniers because it is already set up that way, it is an older "touring" bike so the geometry is a little more relaxed, and I'm accustomed to riding her all the time.
My LBS told me about some cogs that fit together so it's possible to have two on one side of the hub. If you hit some bad hills, you could manually change gears. Or carry a cog or two with you and swap them out.
Since you are accustomed to riding the bike you know what you're getting yourself into. You may want to map the route on one of these sites that'll give the elevations and grades. Maybe find some local hills that match the ones on the route and see how well you do.